day trip st michaels md

Day Trip to St. Michael’s on Maryland’s Eastern Shore

If your summer plans don’t already include a day trip to the charming town of St. Michael’s on Maryland’s Eastern Shore, it’s about time you planned one. Our Bed and Breakfast on Maryland’s Eastern Shore is the perfect place to escape this summer, especially if you need a bit of solitude and zen-like relaxation. We wouldn’t blame you if all you wanted to do while here is sit back with a good book and relax, but we’d be remiss not to mention all the great things to do on the Eastern Shore, including taking a day trip to the charming town of St. Michael’s.

St. Michael’s is a picturesque harbor town located approximately an hour south of our Rock Hall Bed and Breakfast. USA Today named it one of the top 10 coastal towns in America, so you can count on it being more than worth the drive to spend the day here. Once you’ve had this fill of St. Michael’s, the comfortable accommodations at our Eastern Shore Bed and Breakfast will be waiting for you. Book your room today!

Day Trip to St. Michael’s, Maryland

Though there is more than enough to do in Rock Hall and the surrounding Chesapeake Bay, it’s sometimes fun to get out and explore. A day trip to St. Michael’s on Maryland’s Eastern Shore is a perfect choice! St. Michael’s is a charming town on Maryland’s Eastern Shore, filled with a delightful combination of bustling marinas, delicious restaurants, and one-of-a-kind boutiques. St. Michael’s is also home to the excellent Chesapeake Bay Maritime Museum, which is a great place to learn even more about the history and life on Maryland’s Eastern Shore.

Like many towns on Maryland’s Eastern Shore, St. Michael’s has a lengthy and fascinating history that dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. Today, there are plenty of wonderful things to do in St. Michael’s, centered around its historic square, St. Mary’s Square, and its bustling harbors. Here’s a roundup of eight of our favorite things to do in St. Michael’s on Maryland’s Eastern Shore:

• Get established in the town by taking a self-guided walking tour of St. Michael’s on Maryland’s Eastern Shore.
• Take historic narrated cruises through St. Michael’s Harbor, or charter a boat and enjoy a sailing excursion in The Chesapeake Bay. You can even combine wine tasting with a sailing adventure in St. Michael’s!
• Enjoy some unique shopping in downtown St. Michael’s , where you’ll find a diverse range of shops and art galleries to browse.
• Rent a kayak, SUP, or bike from Shore Pedal and Paddle , and enjoy a day exploring St. Michael’s on Maryland’s Eastern Shore, just as you would beautiful Rock Hall, MD.
• Visit the Chesapeake Bay Maritime Museum and learn all about the history of this unique part of the world.
• Sometimes, there’s nothing better than relaxing with a cold pint of locally crafted beer on a hot summer day. You’ll find some delicious craft brews at Eastern Shore Brewing in St. Michael’s.
• Plan to attend at least one of the fun festivals in St. Michael’s! The most popular ones include WineFest at St. Michaels in April, St. Michaels Brewfest in May, and the Wine & Food Festival and OysterFest in October.
• Don’t forget to eat plenty of crab , oysters , and other local delicacies – it’s part of everyday life here on Maryland’s Eastern Shore, and it’s no different at the best St. Michael’s restaurants .

The Best Place to Stay on Maryland’s Eastern Shore

Though spending a day in the charming town of St. Michael’s is a wonderful thing to add to your itinerary to Maryland’s Eastern Shore, there’s something other-worldly about staying on our 70 zen-like acres near Rock Hall, MD. Our Eastern Shore Bed and Breakfast is rated as one of the best places to stay, and it won’t take you long to see why for yourself.

Maryland’s Eastern Shore is an easy escape from crowded cities like Baltimore, Washington D.C., and Philadelphia – and no matter the time you visit, you’ll find this beautiful part of the world serves as the tranquil and refreshing paradise you’ve been looking for.

Our Bed and Breakfast on Maryland’s Eastern Shore offers so much more than a comfortable place to call home at the end of the day. Though our accommodations are exceedingly comfortable, you’ll find that staying here goes far beyond a simple place to sleep. The amenities included in your stay, attention to detail, and exceptional hospitality work in concert to set our Eastern Shore Bed and Breakfast apart from its competitors.

Moreover, we’ll prepare you a fresh and delicious breakfast each morning of your stay. It’s the perfect fuel for whatever adventure lies ahead, including a day trip to the quaint town of St. Michael’s. Though you aren’t very far away from bustling metropolises, you’ll feel like you’re on an entirely different plane. It’s one of the best parts about staying with us on Maryland’s Eastern Shore. Isn’t it time you booked your room at our luxury Bed and Breakfast?

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How to Plan the Ultimate Day Trip to St. Michaels, MD

Are you looking for hidden gems along Maryland’s Eastern Shore? While there is plenty to see and do in historic Chestertown, many of our guests enjoy a day trip to St. Michaels, MD, during their stay. Filled with bustling marinas, fabulous restaurants, and one-of-a-kind boutiques, this charming waterfront town is well worth the visit. Here’s what you’ll discover when you go!

Things to Do in St. Michaels, MD

Whether exploring by land or sea, you’ll love every second of your visit to St. Michaels, MD. Once known as a hub for shipbuilding and oystering, this Eastern Shore of Maryland town is now a prime destination for boaters, outdoor enthusiasts, and history buffs alike. Spend a day exploring museums and historic sites, kayaking along beautiful creeks and rivers, or sipping through some of Maryland’s best wineries, breweries, and distilleries. The possibilities are endless!

For a day trip, we recommend adding the following activities to your itinerary:

1. Visit the Chesapeake Bay Maritime Museum

If there’s one thing you must do in St. Michaels, it’s visit the Chesapeake Bay Maritime Museum ! This 18-acre interactive museum features an excellent collection of Chesapeake Bay artifacts, exhibitions, and a floating fleet of historic boats. Take a step back in time and learn about the history and culture of our gorgeous region. Climb to the top of the 1879 Hooper Strait Lighthouse and enjoy breathtaking harbor views. Or, hop aboard the museum’s 1920 Winnie Estelle boat and enjoy a scenic river cruise. One thing’s certain: you won’t run out of ways to explore at the Chesapeake Bay Maritime Museum!

Are you looking for even more history? Here’s another look at the unique Chesapeake Bay history .

2. Take a Boat Tour Along the Miles River

Speaking of boat tours, here are two other great river cruises to add to your list! Patriot Cruises offers some of the best historical, narrated cruises in St. Michaels. Enjoy the ride as your experienced guide tells you about the town’s history, which dates back to the American Revolution. Along the way, you’ll see 300-year-old Victorian mansions, beautiful scenery, and native wildlife. Keep an eye out for dolphins and osprey!

Sail Selina II also offers excellent Chesapeake Bay boat tours and sailing charters in St. Michaels, MD. This luxury sailing yacht can accommodate six guests, so it’s perfect for those looking for a more intimate experience.

3. Reconnect With Nature

St. Michaels is an outdoor enthusiast’s dream, from fishing and boating to sailing and kayaking. Would you like to spend a day on the water? Enjoy a relaxing paddle along San Domingo Creek, Oak Creek, Miles River, or Leadenham Creek. Are you planning to do some fishing while on vacation? Cast a line right into the Bay for catfish, largemouth bass, and rainbow trout.  If you’d like to get your adrenaline pumping, rent bikes and pedal along scenic Route 33 or impressive nature trails .

4. Dive Into History at St. Michaels Museum

Calling all history buffs! Located inside a 19th-century home, the St. Michaels Museum features regional exhibits and walking tours. Docent-led tours are held on Saturdays at 10 a.m. from May through October. However, you can also schedule a self-guided tour any day you please.

5. Sample Delicious Wine, Brews, and Spirits

When you’re ready to unwind, check out some of the breweries, wineries, and distilleries in St. Michaels. Lyon Distilling is a favorite spot for locals and visitors alike. This popular nano craft distillery is especially famous for its small-batch rum. Stop into the tasting room (it’s open seven days a week) and sample some of Maryland’s finest liquors!

Perhaps you’re in the mood for an ice-cold beer? Enjoy a tasting at Eastern Shore Brewing ! The oldest brewery on the Eastern Shore of MD, it’s also one of the best. From amber ales and hoppy IPAs to dark and delicious porters, their award-winning brews will surely impress!

Wine lovers will want to make a stop at St. Michaels Winery . This local winery is open Thurs-Mon and has 20+ delicious wines. Dry-wine flights, sweet wine flights, and by-the-bottle options are available. No reservations are required, so feel free to drop in and try them all!

Dining in St. Michaels, MD

Are you craving fresh Maryland blue crab? Or perhaps you’re in the mood for authentic Italian, Irish, or Southern cuisine? When it comes to restaurants while on your day trip to St. Michaels, the hardest decision you’ll have to make is which one to try first. From casual crab houses to romantic bistros and fine dining establishments, there are many fantastic places to drink and dine. Here are some of our top recommendations for a day trip:

1. Ava’s Pizzeria and Wine Bar

This cozy restaurant is one of the town’s most popular eateries for a reason. Stop into Ava’s for delicious Italian fare, wood-fired pizzas, and seafood fresh from the Bay.

2. The Crab Claw

Nothing compares to the taste of fresh Maryland blue crab! This local crab shack opened in 1965 and has served delicious seafood ever since. Open March through October, The Crab Claw is as seasonally fresh as it comes! Enjoy beautiful views of the Miles River while you dine.

3. Limoncello Italian Restaurant and Wine Bar

You must try Limoncello’s if you’re looking for an authentic Italian dining experience. With entrees like Ravioli con Astice, Linguine con Vongole and Pappardelle allo Zafferano, each mouthwatering dish sounds better than the last! There is also an excellent selection of exclusive Italian wines and seasonal cocktails in a casual dining atmosphere reflecting the beauty of Southern Italy.

4. Bistro St. Michaels

Bistro St. Michaels is a favorite brunch and dinner spot with a romantic ambiance and delicious New American fare. The menu features an array of hors d’oeuvres, savory soups, salads, entrees, and wine. We highly recommend the Coq Au Vin and Lamb Ragout!

5. Justine’s Ice Cream Parlor

Certainly after lunch or dinner, you’ll want to stop into Justine’s Ice Cream Parlor for some of the best scoops along Maryland’s Eastern Shore. Choose from 42 premium flavors of hand-dipped ice cream, soft-serve ice cream, frozen yogurts, sorbet, and sherbets!

Shopping in St. Michaels, MD

On your day trip to St. Michaels you’ll also find fabulous shopping opportunities. Here, you’ll find unique antique stores, trendy boutiques, nautical-themed specialty stores, art galleries, and so much more. The following are some of our favorite shops:

1. Chesapeake Trading Company

If you’re on the hunt for a new outfit, head over to Chesapeake Trading Company . This casual yet chic boutique store has a great selection of men’s and women’s apparel, jewelry, home goods, gifts, books, music, and more.

2. Ophiuroidea

Also called “The O” by locals, this coastal-inspired boutique features an array of clothing, handcrafted nautical items, mermaid art, sea glass jewelry, coastal furniture, and home goods. Check them out for one-of-a-kind finds!

3. Simpatico

Foodies will love shopping at Simpatico , a little piece of Italy in the heart of St. Michaels. Here, you can find exclusive “Made in Italy” items such as fine wine, artisan cheeses, meats, olive oils, pasta and risotto, desserts, and much more. They also carry a unique selection of ceramics and gift baskets.

4. Antiques on Talbot

For Eastern Shore antiques, take your time browsing Antiques on Talbot. This famous antique shop features everything from oyster plates and sterling silver to artwork, quilts, linens and more.

5. Silver Linings

Are you looking for a dazzling new necklace or a pair of nautical earrings? Stop into Silver Linings for genuine sterling silver and gemstone jewelry. We especially love the unique Chesapeake Bay-themed collection.

Come Home to Brampton Inn For a Great Night’s Rest

Finally, after a fabulous day trip to St. Michaels, MD, return to our historic Chestertown Inn to relax and unwind. Brampton Inn offers the most romantic and comfortable lodging experience along the Eastern Shore. Located just one hour from St. Michaels, our Inn allows you to see another storybook destination of Maryland during your getaway. Plus, Brampton is just minutes from Chestertown’s best restaurants, shops, and things to do . If you’re looking for luxurious accommodations , top-notch amenities, and delicious food, this is the ideal choice for your getaway!

During your stay at Brampton Inn, you can expect to start each morning right with a delicious, homemade breakfast to send you on your way. After a day of exploring the picturesque town of St. Michaels, kick back and relax in your private room or cottage. Or, join us for our complimentary Afternoon Tea Time and Social Hour .

Are you ready for an unforgettable vacation along Maryland’s Eastern Shore?

Check Availability Now .

Updated March 2024

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16 Best Things To Do In St. Michaels, Maryland

The best ways to spend your time in “the town that fooled the British.”

Where To Eat

Where to drink, where to stay.

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The beating heart of Maryland’s Eastern Shore, this nook of a town on the Chesapeake Bay has an individual spirit steeped in maritime history. At once a languid small town full of charm and a bustling vacation town within an hour and a half drive from Washington, D.C. , St. Michaels positively shines in the summer. Rich in history (the town was founded way back in 1677) and proud of its nickname as “the town that fooled the British” in the War of 1812, St. Michaels is also known, of course, for its Maryland crabs, the season of which runs April through November. The charming, walkable downtown is lined with Victorian buildings now housing local shops and outfitters. Although it does put on a stunning show in the summer, St. Michaels is the quintessential Eastern Shore getaway anytime of the year. 

Learn About the Area’s History

St. Michaels and the surrounding area are rich in history and have centuries' worth of stories to tell. The compact St. Michaels Museum centers its exhibits on 19th-century local history and offers excellent historic walking tours, including a tour offered the first Saturday of every month that explores Frederick Douglass’ three years in St. Michaels. 

stmichaelsmuseum.org , 201 East Chestnut Street, St. Michaels, MD 21663

Examine Maritime Artifacts and Vessels

Head to the waterfront Chesapeake Bay Maritime Museum for an overview of hundreds of years of St. Michaels history through a rich collection of Chesapeake Bay artifacts, exhibitions, and vessels. The museum offers a host of public programs and workshops, including the Apprentice for a Day Shipyard Program for the curious of all ages.

cbmm.org , 213 North Talbot Street, St. Michaels, MD 21663

Window Shop

St. Michaels is a town made for strolling and South Talbot Street, which runs the length of the village, is where you should begin. Olde Town Candy Company, The Preppy Redneck , Chesapeake Trading Company, and The Shops at Sea Captain’s Cottage are town mainstays.

Head Out On the Water

No trip to the Eastern Shore is complete without heading out on the Bay. Sail Selina II offers a wealth of options for enjoying and exploring the Chesapeake, from two-hour day-time water tours, to wine and beer tastings on the water, to moonlit sails, to private charters. Their guides are equally schooled in history and safety, and provide in-depth context for your visit to St. Michaels and the wider Chesapeake Bay region. 

sailselina.com , 101 North Harbor Road, St. Michaels, MD 21663

Pedal Your Way Around Town (and Beyond)

Why walk when you can bike? Cruiser bikes provide the perfect mode of transport for exploring the town and the waterfront. For an extended bike adventure, pedal your way to the Oxford-Bellevue Ferry, and board the historic vessel (it’s believed to be the nation’s oldest privately operated ferry) for a 10-minute ride across the Tred Avon River. Many local hotels have bikes available for guests; Shore Pedal & Paddle offers rental options as well. 

shorepedalandpaddle.com , 500 South Talbot Street, St. Michaels, MD 21663

Grab a Bite in Oxford

In Oxford, sit fireside at the quaint Robert Morris Inn and order the Smoked Bluefish Pate Crostini. The seafood-forward Capsize OXMD offers waterfront views, cocktails, and appetizers like Jumbo Lump Crab Balls and Crab Cocktail. Follow up with handcrafted ice cream scoops and sundaes at Scottish Highland Creamery . With 600 flavors in rotation, visitors will always find something new.

robertmorrisinn.com , 314 North Morris Street, Oxford, MD 21654

capsizeoxmd.com , 314 Tilghman Street, Oxford, MD 21654

scottishhighlandcreamery.com , 103 South Morris Street, Oxford, MD 21654

Pamper Yourself at the Spa at Harbour Inn

Enjoy a couple's massage or book some solo time at the Spa at Harbour Inn . Services include hot stone massage, paraffin hand and foot treatments, seasonal facials, body scrubs, and wraps. Extend your relaxation with an overnight stay at the Harbour Inn . Many rooms and suites are appointed with private balconies overlooking the harbor. Dine on-site at the inn’s Harbour Lights restaurant with water views, sit poolside, or tour the area on hotel bikes.

spaatharbourinn.com , 101 North Harbor Road, St. Michaels, MD 21663

Enjoy Oysters at Ruse

Ruse , located in hip The Wildset Hotel , takes its name for the legendary trick the people of St. Michaels used to save the town from a British invasion in the early 19th century. Serving as both a touch point for hotel guests and a meeting place for locals, the restaurant’s menu is Chesapeake Bay-centered and features an impressive list of oysters from up and down the East Coast.

ruserestaurant.com , 209 North Talbot Street, St. Michaels, MD 21663

Order Bottomless Mimosas at The Galley

Down South Talbot Street, The Galley is what small-town restaurant dreams are made of: lively dining rooms and a line out the door on weekend mornings. The restaurant serves bottomless mimosas every Sunday and partaking in the celebration is practically a rite of passage here. The menu includes cold-pressed juices, local handmade crabcakes bene, omelettes, and a maple waffle sandwich. The 1806 building also is home to a popular top-floor Tree Top Lounge which is a local favorite spot to grab a post-dinner drink.

thegalleysaintmichaels.com , 305 South Talbot Street, St. Michaels, MD 21663

Feast on Seafood at The Crab Claw

For a quintessential Maryland seafood experience, head to The Crab Claw . The waterfront restaurant is a relaxed, decades-old, come-as-you-are institution. Get your fill of fresh seafood here–there are plenty of dishes to try, like Oysters Casino, Maryland Crab Soup, steam buckets, and sandwiches. For traditionalists, crabs with Old Bay seasoning are the thing to order.

thecrabclaw.com , 304 Burns Street, St. Michaels, MD 21663

Savor a Casual Meal at Foxy's Harbor Grille

Foxy’s Harbor Grille is another great, local-approved casual dining option serving Caribbean-style dishes, seafood, handhelds, and specialty cocktails. Located in the St. Michaels marina, this spot has some of the best waterfront views and a deck that's perfect for warmer weather.

foxysharborgrille.com , 125 Mulberry Street, St. Michaels, MD 21663

Reserve a Table at STARS

For an upscale dinner, or special occasion, head to STARS at the Inn at Perry Cabin , which seats guests both in their dining rooms and also arranges private, waterfront tables. The three-course tasting menu changes daily and draws heavily from what’s in season—crabs, oysters, lobsters, as well as local produce. 

innatperrycabin.com/dining/stars , 308 Watkins Lane, St. Michaels, MD 21663

Get a Pint at Eastern Shore Brewing

Before or after dinner, stop in for a beer at Eastern Shore Brewing . Selections range from seasonal beers, flights, and growlers to go. Enjoy events like live music and trivia throughout the week. Try the St. Michaels Amber Ale, their flagship beer.

easternshorebrewing.com , 605 South Talbot Street, St. Michaels, MD 21663

Sample Spirits at Lyon Rum

Visit the Lyon Rum distillery to learn about the small-batch process, taste their signature and seasonal American rums, and purchase some to take home with you. Rum liqueurs like Coffee Rum and Curacao Orange are infused by hand, and their rums are distilled in traditional pot stills using Louisiana cane sugar.

lyonrum.com/visit-the-distillery , 103 East Marengo Street, St. Michaels, MD

Inn at Perry Cabin

Stay in the Historic Inn at Perry Cabin

The historic Inn at Perry Cabin looms large in St. Michaels. The classic resort went down in film history for being part of the cult-hit movie Wedding Crashers, but today guests will find a stay here an elegant, peaceful, and secluded affair. The Inn boasts 26 acres of gardens, orchards, lawns, and shore. Its restaurant, as well as a highly regarded spa and golf course, keep guests returning year after year.

innatperrycabin.com , 308 Watkins Lane, St. Michaels, MD 21663

Relax in Style at The Wildset Hotel

The Wildset Hotel , a Scandinavian-chic boutique hotel stretched across four 19th-century buildings, burst on the scene in 2021 and places you centrally in the buzz of the town. Breezy modern rooms, firepits, and its Chesapeake-centric restaurant make this a standout. 

thewildset.com , 209 Talbot Street, St. Michaels, MD 21663

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St. Michaels Is Great For

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• Inn At Perry Cabin
• St. Michaels Harbour Inn, Marina & Spa
• St. Michaels Inn
• The Old Brick Inn
• The Wildset
• Bistro St. Michaels
• Foxy's Harbor Grille
• Limoncello Italian Restaurant & Wine Bar
• The Crab Claw
• Chesapeake Landing
• Tilghman Island
• Chesapeake Bay Maritime Museum
• Spa at Harbour Inn
• 1879 Hooper Strait Lighthouse
• Saint Michaels Winery

Ultimate Day Trip to St. Michaels, MD

Small seaside communities, such as Saint Michaels, typically boast a rich history, attract tourists, and exude charm. Saint Michaels is a prime example of this. Its name originates from the first church built in the area, which drew in settlers who began constructing boats and cultivating tobacco. Today, it remains a charming and peaceful town in Maryland, perfect for a leisurely day trip. The waterfront is stunning, with eclectic boutiques, exceptional dining options, and bustling marinas to explore.

Shopping in St. Michaels, MD

The shopping opportunities in St. Michaels are great. There are plenty of art galleries, nautical-themed specialty stores, boutiques, and antique stores. The top 5 shops on our list are:

Silver Linings , a stunning jewelry store where you can buy sterling silver jewelry adorned with gemstones. They even have their own unique Chesapeake Bay-themed collection.

Antiques on Talbot , an eclectic antique store on Talbot Street that has everything from oyster plates to linens, quilts, and artwork, to name only a few.

Simpatico , a foodie’s dream come true. If you’re looking for genuine Italian imports like desserts, risotto, pasta, olive oil, meats, artisan cheeses, and fine wine then Simpatico is your paradise right in the heart of St. Michaels. You will also find unique gift baskets and ceramics here.

Ophiuroidea , a boutique inspired by the beauty of the coast. Here you will find unique home goods, furniture, sea glass jewelry, mermaid art, handmade nautical items, and a wide variety of clothing. And if you cannot pronounce the name, do not fear! Locals refer to the boutique as The “O”.

Chesapeake Trading Company , another boutique that holds a variety of apparel, music, books, gifts, home goods, jewelry and much more.

Dining in St. Michaels, MD

The thing about a coastal town is that the seafood is always top-shelf. But in this Maryland town it doesn’t stop there. They also specialize in Southern, Irish, and Italian cuisine. The only problem is deciding which eaterie to try first. Catch a drink or have a great meal at one of the amazing local places. The St. Michaels area is home to anything from fine dining establishments to casual crab houses.

Justine’s Ice Cream Parlor  is the perfect place for an after-dinner treat. They have 42 flavors to choose from, and they do hand-dipping. But that’s not all. Also, try their sherberts, sorbet, frozen yogurts, and soft-serve ice cream.

Crab Claw  is home to amazing fresh Maryland blue crab. Enjoy the taste of amazing food while taking in the spectacular view of the surrounding Miles River.

Ava’d Pizzeria and wine bar  is one of the most popular eateries in Saint Michaels. Wood-fired pizzas and delicious Italian fare are right at home here in the Bay.

Best Things to Do in St Michaels, Maryland

St. Michaels used to be known as a shipbuilding and oystering Colonial village on Maryland’s Eastern Shore. Today the charming town is full of activities like fishing, kayaking, and sailing, along with idyllic little shops and waterfront restaurants. Saint Michaels is a great place to visit regardless of the time of year. Coastal restaurants are great; there is a local rum distillery, an iron mill, and a late 1800s lighthouse, and several museums. It might be a good idea to call places ahead of time and confirm opening times and availability. We have made a list of the most popular attractions in St. Michaels.

Patriot Cruises

Patriot Cruises is the perfect way to take a relaxing boat trip down Miles River. Their cruises are 75 minutes and take guests along a scenic route to see beautiful locations. Like the 200-year-old mansion where Wedding Crashers was filmed. Oh, and yes, you’ll be traveling down the waterfront in a steamboat. Throughout the tour the captain will be relating the many stories they know about St. Michaels inhabitants, the Battle of 1812, and the Chesapeake Bay watershed’s history. Passengers can also come to the Pilot House where they can learn how the vessel works.

The narrated cruises in St. Michaels are not the only boat tours in the area. For sailing charters and Chesapeake Bay boat tours in a luxury sailing yacht, try out Sail Selina II. Since there are only six guests allowed on this tour, it is great for smaller groups.

St. Michaels Crab and Steak House

We have briefly mentioned St. Michaels Crab House earlier, but it is so famous in this town on Maryland’s Eastern Shore that we had to give more details. In 1994 Michaels Crabhouse first opened its doors in St. Michaels. However, the name was later changed to St. Michaels Crab & Steak House. The building that is home to the St. Michaels Crab house was built in the 1830s and was once used for oyster shucking. Meals are all made to order and all seafood is fresh from the Eastern Shore sea.

Chesapeake Landing, St Michaels, MD

Another restaurant on our list is Chesapeake Landing where you can also buy fresh seafood to prepare at home. Today the place is known for having the best marine-inspired dishes in the Mid-Atlantic. They also serve burgers and Certified Angus Beef steaks, baby back ribs, and chicken entrees. Their crabs and oysters come from local vendors and are used in the restaurant but also sold in the market.

Bistro St. Michaels, St Michaels, Maryland

While we’re talking about restaurants we have to mention the Bistro St. Michaels. The head chef is from Talbot County and the establishment was opened to serve traditional meals with a modern touch. Today the establishment serves American cuisine prepared with European techniques. Ingredients are sourced from locals and are organic and free-range. All of their produce is sourced from sustainable and humane farmers.

208 Talbot, St Michaels, Maryland

If fine dining is more your speed, try 208 Talbot. The building is vintage and the space is intimate, and the food is amazing. The menu features local Chesapeake fare that can be described as “New American” where you can enjoy gluten-free dishes, vegetarian, duck, filet mignon, lamb, and seafood dishes. The dessert menu is also a feature of interest with its angel food cake, cheesecake, and classic bread pudding.

You will find a full-size bar at 208 Talbot, where you can order bespoke cocktails, various beers, and a great variety of wines. Furthermore, if you want to visit 208 Talbot, but fine dining is not for you, then you can order from the separate Tavern menu which ensures a more casual experience for diners.

Iron Will & Woodworks, St Michaels, Maryland

Like many other establishments in St. Michaels, this woodwork shop was founded by a married couple who has been restoring and rebuilding vintage wood pieces for many years. They also teach the intricacies of wood and ironworking. The location of their business was chosen for its local history, and the focus of the business is to restore home decor, bars, furniture, fixtures, etc.

Michaels Museum, St Michaels, Maryland

The historic district of St Michaels is a major tourism draw for the town, and the St. Michaels Museum is a great stop on a historic tour through town. The museum is community-focused and aims to create a bond between tourists and locals. The environment at the museum is inviting and visitors can join a guided walking tour where museum staff will explain the important historic elements of each exhibit. The museum also has programs aimed at children, whether for a school visit or a trip with their families. If you miss the guided tours at St. Michaels Museum then you can still take a self-guided tour any day of the week.

Lyon Distilling Co., St Michaels, Maryland

In 2012 Jaime Windon co-founded the Lyon Distilling Company after spending years trying to perfect the art of mixology. Her experience as a bartender and her enthusiasm for locally crafted spirits drove her to open Lyon Distilling. By the end of 2013 they had launched a custom line of signature rum. These drinks are meant to pay tribute to the Eastern Shore and specifically Chesapeake Bay. Visitors can tour the distillery and enjoy some tastings.

Chesapeake Bay Maritime Museum

The second of three museums on our list is the Chesapeake Bay Maritime Museum which spans 18- waterfront acres. In the past this area was home to seafood packing houses, but the museum was built and officially opened in 1965. The goal of the museum was to display the history of Chesapeake Bay in terms of geography, society, and economy. Exhibits map the transition between sailboats, steamboats, and eventually gas engines. The museum also collects Chesapeake Bay watercraft and today has around 80 historic boats in its collection.

This museum actually makes for such an exciting stop that we recommend it above any other history stop on our list. The Chesapeake Bay Maritime Museum in St. Michaels is truly a must-see installment. Even your kids will love to explore the Chesapeake Bay Maritime Museum.

1879 Hooper Strait Lighthouse

The Hooper Strait Lighthouse is a great place to visit to grab a panoramic view of the surrounding harbor area. For many years the lighthouse served its purpose of guiding boats through the Hooper Straight into the harbor. Today the lighthouse is part of a 1920s-themed museum.

Spirits, Brews, and Wine

St. Michaels has quite a few distilleries, wineries, and breweries, and we have already talked about the Lyon Distilling Co. But there are also other booze-based attractions, like St. Michaels Winery, where visitors can sit down in the tasting room and enjoy a journey through their delicious wines. Lastly, St. Michaels, MD, is also home to amazing craft breweries serving anything from dark porters, and IPAs, to amber ales.

Take a Breath of Fresh Air

If you love the outdoors then St. Michaels, MD, will not disappoint. There are many opportunities for kayaking, sailing, boating, and fishing. Visitors can easily spend a day on the water, like a proper East Coast weekend getaway. Kayaks can be rented and taken down Leaderham Creek, Miles River, Oak Creek, and San Domingo Creek. Fishing is a highly popular pass time, especially in places like Waterman’s Wharf and Tilghman island. The Bay is full of rainbow trout, largemouth bass, catfish, and carp.

Closing Thoughts

You can check out the St. Michaels Business Association website for further tourist information. We recommend Talbot Street, St. Mary’s Square, and The Maritime Museum for a peek at Chesapeake Bay artifacts. It also has the largest collection of watercraft that we have ever seen. Nearby on Mulberry street you can visit the Cannonball house, or you can peruse some of the many gift shops and historic attractions around town. St. Michaels has something for everyone and is a great summer getaway destination.

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How to Plan a Perfect 24-Hour Getaway to St. Michaels, Maryland

The historic waterfront town is brimming with hot new hospitality options, quaint cafes, Euro-chic bars, and much more

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After crossing the Chesapeake Bay Bridge, follow U.S. Route 50 down the Delmarva Peninsula and hook west along the scenic stretch of Route 33 to stumble upon Maryland’s coastal cottage town of St. Michaels. Part of the beauty of this idyllic destination – just a 1.5-hour drive from D.C. – is its postage-stamp size. Between the main dining-dense drag of Talbot Street to cute cobblestone side streets leading the way to water, soaking up the picturesque harbor’s top attractions in one day is easy as pie.

For an on-brand Maryland arrival

It wouldn’t be a trip to the Eastern Shore without waterfront orange crushes and blue crabs, so why not dive right in with both. At trusty boater bar Foxy’s Harbor Grille ( 125 Mulberry Street ), order the fresh-squeezed seaside staple by the bucket and Chesapeake’s star crustacean all kinds of ways (crab cakes, soup, sandwiches, and chilled claws). For the ultimate crab-cracking, Old Bay-blasted experience, decades-old seafood house The Crab Claw ( 304 Burns Street ) is the move. Trays topped with steamed crab stay in season here through October. To quench post-picking cravings for beer, head to local pioneer Eastern Shore Brewing ( 605 South Talbot Street ) to sample its award-winning St. Michaels Amber Ale flagship in an old-world setting. Sip and stay on its gravel-lined patio or grab a growler and take the party to-go.

The heart of St. Michaels upped its laid-back luxury game in summer 2021 with the anticipated arrival of the Wildset — a stylish, 34-room boutique hotel where a check-in desk doubles as a hip cafe with Ceremony espresso drinks scribbled on a big brown paper roll next to a well-curated sundry shop. Settle into the nautical-chic sanctuary fit for Vogue by flicking on a matte fireplace and relaxing on a private balcony or porch with a read from the room. Complimentary guest perks include custom bikes to roam around town and an abundant breakfast spread full of fresh pastries, coffee, and yogurt. The manicured grounds will soon grow with a pool. For now, lounge around a stone-framed fire pit at twilight to toast s’mores. 209 Talbot Street

Other options: For an elegant harborside bed-and-breakfast with antiques-filled rooms, consider the restored Hambleton Inn ( 202 Cherry Street ). And for the ultimate overnight splurge, there’s the luxe Inn at Perry Cabin . Made famous by the movie Wedding Crashers , the postcard-perfect resort is home to special-occasion spot Stars Restaurant ( 308 Watkins Lane) .

Aperitivo hour

A surprise slice of the Italian coast lies right off the main drag. Naples natives run six-year-old standby Limoncello ( 200 S. Talbot Street ), where Italian wines pour freely from a cheery bar alongside a daily lunch-and-dinner selection of homemade pastas and char-grilled flatbread. To stock up the room (or trunk) with bottles of hard-to-find varietals, along with all-imported Italian cheeses, ceramic plate ware, and jewelry, check out charming retail store Simpatico ( 104 Railroad Avenue ) and ask its friendly female staff about their bi-annual trip to Umbria. For more European feels in the center of St. Michaels, consider recently reinvented French restaurant Bistro ( 403 S. Talbot Street ). Originally established in 1995, the cozy stalwart is the spot for steak frites, tuna nicoise salads, and mussels. During happy hour (4:30 p.m to 6 p.m.), enjoy $6 martinis, $7 lemon vodka-infused cosmos, and pimento cheese-stuffed arancini.

The team behind Nashville’s award-winning Henrietta Red brought the strip a chic, seafood-centric American restaurant in summer 2021 with the debut of Ruse at the foot of Wildset. A bright and airy raw bar wrapped in hand-painted terracotta tile swaps customers’ pencil-checked shellfish sheets for shucked oysters sourced from nearby tributaries like Harris Creek and other East Coast waterways. Peak ingredients from local farmers and fishermen dictate dishes of the day, which means the super-seasonal menu changes as frequently as the tide. Tenured chef and Bel Air, Maryland native Michael Correll celebrates summer dishes like crab and ramp rangoon, burrata and strawberries, and shrimp tagliatelle, which all pairs nicely with its natural wine list and well-executed cocktails. 209 N. Talbot Street

Justine’s Ice Cream Parlor , an old-timey Maryland draw for over 30 years, keeps scoops coming until 10 p.m. daily. Its cherry-red facade is hard to miss, inviting diners to indulge in a massive milkshake selection (77 in all), dozens of ice cream flavors, and sundaes. 106 N. Talbot Street

Go for a nightcap, come back for breakfast

Historic tavern Carpenter’s Street Saloon , lovingly called C-Street by locals, is the kind of all-day dive dreams are made of. The brick-lined bar draped in colorful flags doubles as a morning mainstay for scrapple (a Delmarva Peninsula favorite), biscuits and gravy, and home fries. C-Street seamlessly transitions by day into a late-night, no-frills hangout for plastic cups of booze, crab balls, and buzzed requests from a modern-day jukebox that plays just about every song under the sun. 113 S. Talbot Street

A leisurely morning

Check out and swing by roadside roaster Rise Up Coffee ( 1216 St. Michaels Road ) to fuel up on single-origin beans from around the world. This tricked-out, drive-thru trailer is the location that started it all in 2005; the Maryland brand has since ballooned to over 10 outposts. Make room in the trunk and stop by the town’s resident distillery Lyon Rum ( 103 E. Marengo Street) to buy bottles of its popular, small-batch spirits (FYI: an under-construction tasting room with cocktails will debut in the fall). For the ultimate collectable car buff, the Classic Motor Museum ( 102 E. Marengo Street ) is right across the street. For a $10 admission, peruse exhibits of pre- and post-WWII automobiles, mid-century muscle cars, and vintage trucks parked inside a big barn. After hopping in your own car to drive back to reality, be sure to make one meaty pit stop to Easton’s edgy Rude Burger ( 4 S. Aurora Street ) for excellent barbecue and bourbon in a retro pump-station setting. The tiny Maryland town of Easton is also flush with fine-dining restaurants and cafes as of late.

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• How To Spend 24 Hours...

How to Spend 24 Hours in St. Michaels, Maryland

Maryland’s Eastern Shore is home to Ocean City and Atlantic beaches of Maryland and Delaware, but there are also several smaller towns along the Chesapeake Bay worth visiting. Just an hour-and-a-half from both Baltimore and D.C., and right across the Bay Bridge, St. Michaels is perfect for a weekend getaway. Here is how to spend 24 hours in this historic town by the bay.

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Grab a gluten-free treat

Bakery, American, $ When you arrive in town, grab a sweet treat at Gluten Free Bakery Girl. This little shop was started by pastry chef Tricia King, and locals love the delicious breads, buns, and cakes that are all gluten-free. You can also get dairy-free and vegan creations.

Rent a bike and take a ride

Do a half-day or full-day bike rental from TriCycle and explore the area. The roads are very flat and most motorists are used to seeing cyclists. If you want a challenge (and a ride that takes about three hours), pedal all the way down to Black Walnut Point, or just bike around the backroads to enjoy the scenery.

Check out the Chesapeake Bay Maritime Museum

In the afternoon, be sure to visit the Chesapeake Bay Maritime Museum. Celebrating Maryland’s relationship with the water, the museum has boat-building demonstrations, exhibits on the legacy of watermen and fishermen on the bay, a whole building dedicated to the once-thriving and now-recovering oyster industry, and more.

St. Michaels Winery

Wine Bar, Wine Seller, American, $ The tasting room at the St. Michaels Winery is open year-round, so be sure to stop by to taste some wine made right in town. The winery offers samples starting at 11 a.m. each day, with a variety of whites and reds to choose from. They pride themselves on using Maryland-grown grapes for many varieties of their classic wines, while also having fun, summer wines that are perfect for a picnic.

Eastern Shore Brewing

Bar, American, $ If wine isn’t your thing, or you just want to sample more of what St. Michaels has to offer, check out Eastern Shore Brewing down the street. The beers are brewed on-site, so you know you’re getting the freshest beer in town, and the tasting room offers both pints of beer and sampler flights. The space inside is cozy and the perfect place to relax after a busy day.

Sail the Chesapeake on a Patriot Cruise

Museum Before heading home, take a boat cruise on the Chespeake. During the summer months, Patriot Cruises offers narrated historical cruises every day, and Island Music Cocktail Cruises on Saturdays. Tour the water on a replica of a 1930s steamer—the type of boat that crossed the bay to take tourists to bay-side resorts—and learn about the history of the region. The boat has refreshments and air-conditioning.

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Our immersive trips , led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.?>

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Welcome to  St. Michaels, Maryland !

Welcome to St. Michaels, Maryland, one of USA Today's Top 10 Best Small Coastal Towns.  Within a few hours drive of Washington D.C., Philadelphia and New Jersey, St. Michaels is a quaint historic town with a beautiful harbor, exceptional dining, amazing B&B's and Inns and one of a kind shopping.  Join us in St. Michaels for an experience of a lifetime.

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Every day is beautiful in green valley.

With a wide variety of events and opportunities, Green Valley has something to offer everyone. Celebrate the fun of the Minnesota State Fair with us each summer. Enjoy a scenic stroll through our many parks or play a round of golf at one of our three courses. Have your picture taken with the World’s Largest Owl and marvel at all the beautiful outdoor murals throughout the town. Our community offers a thriving economy, superb schools, traditional values, faith and fellowship, helpful services, and many entertainment options. Green Valley is truly the ideal place for new ventures and new growth because every day is a beautiful  day.

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WineFest, Running Festival, Oysterfest, Fall into St. Michaels and Christmas in St. Michaels are just a few of the wonderful festivals held throughout the year. Many of these festivals have been held for years and all feature the beauty of St. Michaels. 

Event Destination

St. Michaels is a wonderful home for your Destination Wedding, Corporate Event or Family Reunion. Our facilities have the ambiance and services to make your event a once in a lifetime memory.

Dog Friendly Paradise

Many Hotels, restaurants, retailers and even local banks all have amenities specific to dogs traveling with their owners, making St. Michaels a heavenly spot for mans best friend.

Best Things To Do In St. Michaels, Maryland

The best ways to spend your time in “the town that fooled the British.”

The Best Waterfront Town In Every Southern State 2024

The Eastern Shore of Maryland has a deep history powered by the water that surrounds it. Its fishing villages, like St Michaels, have thrived thanks to the resources of the Chesapeake Bay and are now destinations filled with natural beauty as well as opportunities for sailing and enjoying freshly caught seafood, including the crabs for which the area is famous.

St Michaels Tourism

We would like to thank the wonderful artists who contributed images to this website including The Town of St. Michaels, The Chesapeake Bay Maritime Museum , The St. Michaels Museum , Susan Hale -Chesapeake Scenes , Tracey Finch Johns, Monte Morton , Eastern Shore Dronography , Dick Cooper , Agent Aerials and Wiliam Wilhelm Photography

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Top Things to Do in St. Michaels, MD

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We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md, we sail april 19,2024 to nov 3, 2024, clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

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2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

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St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

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Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

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Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

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Day Pass: Extend That Endless-Summer Glow With A Trip To St. Michaels

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“The earth belongs to God. Everything in all the world is His!” -Psalm 24:1

St. Michaels, MD

Friday, September 13, 2024

Price per person: $199.00

Walking Guide 3 requires moderate amount of walking possibly on uneven surfaces; longer and shorter days; possible air travel with long walks to terminal gates.

Hear about the Battle of 1812 and cruise aboard the Patriot , hearing detailed history of St. Michaels, the Eastern Shore and the Chesapeake Bay watershed.

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Fri, Sep 13    $199 Pickup: Lancaster, PA    Lv-7:00 am    Rt-9:00 pm

*Arrive for lunch at the Crab Claw Restaurant- included *Cruise aboard the Patriot , hearing detailed history of St. Michaels, the Eastern Shore and the Chesapeake Bay watershed *Hear about the Battle of 1812, the history of the amazing mansions on the Miles River and the great history of the people who lived in our area over the past 300 years *Visit the Chesapeake Bay Maritime Museum, learning about the Chesapeake Bay’s history, traditions, and culture *Browse the shops and have an early dinner before traveling home- on own

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