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Chesapeake Bay Tours

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Annapolis's Favorite

• Charter Cruises up to 32 people
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Annapolis Boat Tours

Tour Boat Annapolis provides boat tours & cruises in Annapolis, MD. Our boat tours are a unique and fun way to experience the beautiful city of Annapolis. We hope to entertain everyone from families, tourists, locals, etc. Come see us to learn about the area, celebrate an occasion, or just get out and enjoy the water. The tour strictly remains in the protected waters of the harbor; from the Naval Academy through Ego Alley and up into Spa Creek. Bring your own food/snacks and beverages if you choose (ice, water, and coolers are provided). There will be no alcohol sales onboard.

2 Charter Boats for Rent in Annapolis

Annapolis Girl

The Annapolis Girl is the smaller vessel in our fleet, featuring sightseeing cruises around the beautiful city of Annapolis, sunset cruises, date nights, celebrations, corporate events, etc.. The Annapolis Girl allows up to 6 guests, creating a more personal, intimate setting for your charter.

Annapolis Lady

The Annapolis Lady is our larger vessel capable of handling up to 32 people. We offer the same sightseeing cruises around Annapolis highlighting its beauty. We also offer sunset cruises, celebration cruises, corporate events, etc. The Annapolis Lady also hosts special event cruises featuring live musical performances from local artists.

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The Marina at Nautilus Point:

710 Americana Drive - Dock F Annapolis, MD 21403

Phone: (443) 333-1030

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ANNAPOLIS 2-HOUR PRIVATE BOAT TOUR

Experience the beauty of annapolis from the water.

On this tour of the charming Annapolis harbor and surrounding waterways, you'll enjoy all the sights and sounds of the city, hearing both historical and personal stories about the city, its merchants, sailers, and watermen, and more. There's a reason sailors from around the world rank Annapolis as their favorite port call––it's one of the prettiest seaside towns on the East Coast. We'll get close-up views of power boats, sail boats of all sizes, and even a yacht or two. You'll learn about the settlement of the Chesapeake Bay, Annapolis, and the adjacent rivers, and also hear the story of the "Annapolis Tea Party" in 1774! Your tour guide, a native of Annapolis, boater, and sailor, will share personal adventures on the waters––capsizing in high winds, "skulling" on windless days, and evening races in the summer. As always, questions are welcome about whatever captures your interest.

Sample Itinerary

ANNAPOLIS CITY DOCK: * State House

* Ego Alley

* Kunta Kinte–Alex Haley Memorial * Main Street * Market House * Annapolis skyline

SPA CREEK / CARROLL'S CREEK, including views of: * St. Mary's Church * Charles Carroll House * Many beautiful private residences * Dozens of docked boats and sailboats ANNAPOLIS HARBOR: * Sailing Clubs * Marriott Hotel * Annapolis/Eastport drawbridge SEVERN RIVER: * US Naval Academy

Meeting Point:

Dock of Chart House Restaurant (300 Second St.)

Important Notes:

– There is no bathroom aboard the Electric Boats, so please use the facility available at the dock before we depart.

– Life-vests and flotation devices are supplied on the boat; you don't need to bring your own.

– Our trip will begin with a brief safety lesson to make sure everybody knows what to do in case of an emergency.

Activity Level:

Minimal. The boats have comfortable, cushioned seats.

Children–Friendly: 

Yes, children are welcome and will find much to enjoy on this tour!

Handicap–Friendly:

Embarking and de-barking the boat can be difficult for those with mobility impairment. Please contact me with your specific needs, to see if they can be accommodated. 

TOUR PRICE:

$550  weekday  /    $595  weekend, for up to 9  guests   (duration: 2 hours).

Questions about this tour? Contact me for answers, or to customize this tour for you and your party.

Wine and Dinner Cruises on the Chesapeake

July can be steamy or dreamy – hot on land but much cooler on the water.  Watermark Cruises and the Schooner Woodwind offers a range of options for getting out on the scenic Severn River or the majestic Chesapeake Bay. These well- established local companies provide unique adventures of varying durations – from on-demand water taxis to foodie-favorite wine and dinner cruises.

Watermark has a fleet of boats, ranging from the popular Harbor Queen , a replica of an old river boat that leaves City Dock every few hours for a 40-minute cruise around the Annapolis Harbor to round trip cruise on a catamaran motor boat named Lady Sarah that takes passengers on a glorious round trip from the City Dock to the picturesque town of St. Michael’s on Maryland’s Eastern Shore. This perfect “day on the bay” is a double-edged treat, with fare that includes a complimentary ticket to the Maryland Maritime Museum, the boat’s docking destination in St. Michael’s. Ticket holders for the cruise have a three-hour layover in St. Michael’s, a town with many good restaurants – among them the Crab Claw (super casual) and the elegant Inn at Perry Cabin.

Other members of the Watermark fleet are the Miss Anne , a cozy 22-seater that plies the coves of Carrol’s Creek and Cabaret II, a motorized craft whose route focuses on lighthouses on the bay. And there’s one more boat in the fleet – a water taxi . Call the Watermark Captain at 410-263-2033 if you need a water taxi to take you to and from the concentration of good restaurants on the Eastport side of the Annapolis Harbor.  This low-cost on-demand service originates at the City Dock, ferrying passengers to the docks of the Annapolis Chart House , Carrol’s Creek Café and O’Leary’s Seafood Restaurant and to walking-distance destinations like Ruth’s Chris, Boatyard Bar & Grill and Lewnes Steak House.  P.S. Watermark folks are pet friendly, welcoming leashed and well-behaved dogs on most cruises.

Call Katy 410-268-7601 for more information and go to www.cruisesonthebay.com for reservations and schedule.

Schooner Woodwind & Woodwind II, a pair of gorgeous 74-foot wooden boats, offer a winning variety of on-the-water excursions ranging from daily two-hour cruises to Saturday night “Boat and Breakfast” accommodations that include a two-hour sunset sail and sunrise breakfast on the deck.  “Party Like a Sailor” events provide a taste of sailboat racing, with both schooners competing with each other during the popular Wednesday Night Races sponsored by the Annapolis Yacht Club. Reservation holders are entitled to a Cuzon Rum Punch beverage on board and another at the informal “after party” at the Boatyard Bar and Grill in Eastport.

Schooner Woodwind owner and seasoned sailor Jen Kaye is also a “foodie,” who masterminds “Wine in the Wind” evenings.  Tickets are still available for August 27, a Spanish-themed two-hour sail featuring four wine samples “perfectly paired with magnificent morsels” provided by prime time Annapolis caterer Palate Pleasers.  Kaye will showcase the wines of Maryland’s Dodson Vineyards at a special dinner on August 20, when the menu will include a rose paired with a ceviche of scallops and shrimp, chardonnay with jumbo lump crab salad, red with beef medallions and a floral white with a dessert torte.  At this point, there are nine remaining reservations.

Captain Kaye will celebrate Schooner Woodwinds’ 25 th anniversary in 2018 – during which time Schooner II achieved international celebrity as the “star” of the movie “Wedding Crashers.” These two photogenic schooners are the setting for corporate team building sessions, wedding rehearsals and receptions and high-end social gatherings.  Scheduled cruises happen rain or shine or with only one person on board. Their home port is the dock at the Annapolis Waterfront Hotel , where they depart for two-hour cruises at 11 am and 1:30, 4 and 6:30 pm.  Join the crew with a call to 410-263-7837 for more information and go to www.schoonerwoodwind.com for reservations and schedule.

Photos courtesy of Cruises on the Bay by Watermark and Annapolis Sailing Cruises: Schooner Woodwind .

Mary Lou Baker

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26 west street annapolis, md 21401, [email protected], phone: 410-280-0445, toll-free: 888-302-2852, fax: 410-263-9591.

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Sailing Season is Here. Join Us for a Sail!

Rates and Schedule

Includes a complimentary soda or water.

Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48).

Tickets go on sale 6 days prior to the date you want to sail.

2024 Public Sailing Schedule

April 13 – april 23, seven days a week.

12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail) * * Friday, Saturday & Sunday only

April 24 – May 10

12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail)

May 11 – August 25

11:00 am – 1:00 pm 1:30 pm – 3:30 pm 4:00 pm – 6:00 pm 6:30 pm – 8:30 pm (Sunset Sail)

August 26 – September 22

10:00 am – 12:00 pm (Saturday & Sunday Only) 12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail)

September 23 – 29

11:00 am – 1:00 pm 1:30 pm – 3:30 pm 4:00 pm – 6:00 pm

September 30 – October 16

No 2 hour public sails due to US Boat Shows Private Charters are available

October 10 – October 14 we will be sailing from the US Sailboat Show

October 17 – October 31

Once tickets are purchased, there are no refunds or exchanges.

We sail rain or shine, unless the captain cancels the cruise due to unsafe conditions. We offer complimentary rain ponchos in case of rain.

Please Remember:

• Only soft-soled shoes are allowed aboard.
• All departures are from Pusser’s Caribbean Grille at the Annapolis Waterfront Hotel across from the City Dock (unless otherwise noted) . Rates and schedules are subject to change without notice. Our schedule may vary due to weather, special events, and group charters.
• Tickets go on sale six days prior to the date you want to sail.   Please call our business office at 410-263-1981.
• Up-to-date schedule information is available by clicking here or calling (410) 263-7837.

Questions???

Please visit our frequently asked questions page.

936 Bay Ridge Ave #106,  Annapolis, MD 21403

Jennifer Holden

Last updated:

September 9, 2024, 12:06 AM

MDAA2093794

About This Home

Bright and welcoming first-floor condo in a wonderful location! Freshly repainted with updated fixtures, bathroom lights and mirrors, and updated dining area, this home has the layout and great closet space you’ve been looking for. The open kitchen features stainless steel appliances and a breakfast bar. This is a secure building and #106 is on the first floor (no stairs). Enjoy living in Eastport, with great restaurants, cafes and shopping within walking distance and a gym right across the street. Keep your boat at a local marina and enjoy life on the water! Just a quick 1 mile walk or bike ride to downtown Historic Annapolis. Welcome to Eastport!

Built in 1995

Price Summary

$268 per Sq. Ft.

Last Updated:

3 day(s) ago

Rooms & Interior

Total Bedrooms:

Total Bathrooms:

Full Bathrooms:

Living Area:

1,175 Sq. Ft.

Architectural Style:

Contemporary

Building Area:

Year Built:

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Annapolis Sunset Cruise

Dates available.

See highlighted dates below.

Upcoming Dates

Sat 6:30 pm - 7:30 pm

Description

Our Annapolis Sunset Cruise takes you out on the water to watch the sunset and see the lights of the Annapolis Harbor. Enjoy a fun music playlist and beautiful scenery as you relax with a cool drink. Beverages and snacks are available for purchase from our full bar.

Looking for our Annapolis Sunset Cruise with Live Music ? Find it here !

No pets on this cruise please! Visit our FAQ page for more information.

Departure Location

Annapolis City Dock 1 Dock Street, Annapolis MD, 21401

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