sail boat tour boston

Classic Sail Boston

Welcome to Classic Sail

Private Charters in Boston Harbor

Classic Sailing

See Boston from a 45' Classic Wooden Sailboat

Sail or Motor

Classic Boston Style 2 Ways

Fun For Any Occasion

Special Occasions, family outings, parties with friends

Libations and Food Welcome

BYOB Encouraged

Classic Sail Charter Options

2 hour private charter.

Sail with us around the inner harbor to see the BEST of Boston including Seaport, Southie, Castle Island, Spectacle Island, Eastie, Charlestown, and The North End. Let us regale you with the history of these places, or just listen to some music and enjoy a leisurely sail around the harbor. We specialize in hosting private events; birthdays, anniversaries, proposals… we do it all. Complimentary soda and water are always on board and you’re welcome to BYOB anything else you wish! Convenient pick up location in Boston’s Seaport District, with custom pick up/drop off locations throughout Boston Harbor upon request.

4 Hour Half Day Private Charter

Sail out to the Boston Harbor Islands on this extended version of our tour. Enjoy sailing around some of the further islands before returning to the inner harbor for the rest of your tour. Or, design your own half day adventure, just tell our captain what you would like to do!

Full Day Private Charter

Spend your day sailing around and exploring all that the inner and outer harbor have to offer.  You are welcome to bring snacks, lunch, libations or anything else you like aboard to enjoy during your day on the water with us. You can explore the islands and lighthouses up close, we can throw the anchor and take a dip, island hop, and get the extended tour of the area. It’s your boat for the day and we’ll make sure its unforgettable! Book Now

2 Hour Daytime / Sunset Sail

Spectacular views of the Boston Harbor skyline, a very relaxing sailing experience for your special event. The perfect stage for a unique moment… Birthdays, proposals, memorials, or simply cruising along.

This is a complete tour of the inner harbor. You will sail by the USS Constitution, the North End, the Seaport District, Castle Island, and East Boston.

Rates: 20% is due at the time of booking. The remaining balance is due at the time of the charter.

• Daytime $545

• Sunset, Weekends, and Holidays $595

• Duration: 2 Hour Charter

• Price includes up to 6 people

• All ages welcome

Charters depart from JSeaport Water Taxi Dock

142 Pier 4 Blvd., Boston, MA 02210

• Plenty of parking nearby.
• Please arrive 15 minutes prior to your scheduled sail time.
• If you are running late, please call 617-279-3981 to notify us as soon as possible.

Weather Policy

• We want you to have the best experience and will only sail in moderate conditions.
• Occasional light rain clouds wind and seas are part of the New England nautical weather experience.
• Only the captain based on his experience has the discretion to cancel a trip for inclement weather.
• You will be informed within 2 hours prior to the trip if there is any concern.
• If the trip is canceled by inclement weather, you will have the option to reschedule or get a full refund.
• We reserve the right to cancel a trip for unforeseen circumstances, in this case, you will be fully refunded.

OUR POLICIES

BOOKING RESERVATION:

• 20% DEPOSIT IS REQUIRED AT THE TIME OF BOOKING.

CANCELLATION POLICY:

• 48 hours prior to the charter, You will receive a full refund minus 10% of the total value of the trip.
• Less than 48 hours, No refund is available
• A no-show is considered a cancellation.

LIFE JACKET POLICY

• Boston Sailing Charters strongly recommends the use of our USCG-approved life jackets for all passengers while on board. We will provide a life jacket to any passenger wishing to wear one.
• Passengers twelve and under are required by law to wear life jackets while on the vessel.
• Parents or guardians are responsible for determining if their minors between the ages of 13-17 must wear a life jacket.
• The person booking the charter is required to share our life jacket policy with all members of their group.

ALCOHOL/DRUG POLICY:

• Customers are welcome to bring beer or wine. No hard liquor
• Per Federal regulation NO marijuana or marijuana-containing products. No illicit drugs

ADDITIONAL TERMS AND CONDITIONS

• Infants and children, regardless of age, are included in the six-person maximum allowed on board. This is a requirement by the United State Coast Guard.
• Gift Certificates are non-refundable and are valid from the date purchased until October 31st of the following charter season.

WHAT SHOULD I BRING?

CONSIDER TO BRING

• Sailors should dress for safety, comfort, and weather. In spring and fall, dress in layers and bring a jacket or sweatshirt; it can be cooler at sea than on land.
• In summer, bring a hat, sunglasses, and sunscreen. 
• For safety and comfort, soft-soled shoes like boat shoes or sneakers are the preferred footwear aboard the Francesca. You will be asked to go barefoot for safety reasons if you wear hard-soled shoes or high heels on board.

WHAT NOT TO BRING

• Per Federal regulation no marijuana or marijuana-containing products no illicit drugs
• No Hard Liquor

FOOD, DRINKS, MUSIC

• You’re welcome to bring your favorite food, drinks, and music.
• We recommend easy-to-eat items and canned drinks. 
• We do not have a formal table in the cockpit
• We have complimentary water and sodas on board

MOTION SICKNESS

• It is very unlikely to get seasick on the harbor. If you think you are extra sensitive consider limiting your trip to the 2-hour Harbor sail.

WHAT IF I AM RUNNING LATE

• We will always wait for you. However, we will conclude your sail at the scheduled finishing time.

PETS & TIPPING

• Pets are welcome aboard if they can sit on your lap at all times.
• Tips are graciously accepted.

BATHROOM:  Bathroom in the Cabin

Departing Location

Seaport Water Taxi Dock

Mailing Address:

28 Constitution Road

Charlestown, MA. 02129

617-279-3981

[email protected]

© ALL RIGHT RESERVED BOSTON SAIL TOURS OWNED & OPERATED BY CGN MARINE LLC. | SITE DESIGN BY  NXTMEDIA

Look for our new autumn schedule and hours! Nothing beats seeing Fall from the deck of a Tall Ship!

Boston Harbor Sunset Sail

Quick details.

• Hour Glass Duration: 2 Hours
• Clock Time of Day: Evening

Monday - Thursday

Must provide valid id at check-in, friday - sunday, young children, sunset sail in boston harbor.

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax.

The Star can accommodate up to 39 passengers for day sails in addition to a crew of 3. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeatable views of the skyline sparkling in the twilight.

Drinks are available onboard for purchase via cash, credit, or Apple Pay – our menu includes several beers brewed right here in Boston! We also have red and white wine, vodka- and rum-based cocktails, soda, juice, and water available in addition to several snack options.

Snacks and bag lunches are welcome, but please no coolers or outside beverages.

There is no formal narration during our public sails, but feel free to ask the captain and crew and they’ll happily share their knowledge of local landmarks and history.

Browse by Boat

• Northern Lights (15)
• Schooners Adirondack III & IV (7)

Browse by Theme

• 4th of July (6)
• City Lights Sails/Cruises (11)
• Day Sails/Cruises (15)
• Fall Foliage (2)
• Family Friendly (19)
• Fireworks Cruises (7)
• Food Cruises (7)
• Harbor Cruises (24)
• Harbor Narrated Cruises (4)
• Holiday Cruises (13)
• Music Cruises (6)
• New Year's Eve (2)
• PRIDE Cruise (0)
• Romantic Sails/Cruises (12)
• Sailing (7)
• Sightseeing Cruise (19)
• Special Events (18)
• Spring Cruises (9)
• St. Patrick's Day (2)
• Sunset Sails/Cruises (6)
• Valentine’s Day (3)
• Terms and Conditions

Boston Sunset Cruise

Call to order 617-951-2460

Cruise on a sailboat or luxury yacht through Boston Harbor to end your day or start your evening.  Set sail aboard one of our classic boats for an experience you are sure to never forget!  Sail through Boston Harbor and glide past the U.S.S. Constitution as the sun dips beyond the outline of Boston’s skyline. Take in the rich colors of the sky with a glass of Champagne in hand and the breeze in your hair. Allow us to help you sit back and relax and enjoy the most perfect Boston sunset cruise.

Whether you are on our sailing boat, or our motor yacht, our exceptional crew is sure to treat you with the most professional hospitality that will have you feeling that it is your own yacht. Cruise Boston aboard one of our classic boats for a peaceful and picturesque sunset. Whether you are sightseeing or wanting to take in the views, it is the perfect way to end your day.

-->Boston Sunset Cruise -->

Join us for a Boston Sunset Cruise as an after work cruise to relax with friends and watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline. Experience a sunset cruise departing from bustling Rowes Wharf and head out to watch the sun go down over the city of Boston. Bring a date or meet a group of friends aboard the classically styled yacht, Northern Lights . Cruise by the U.S.S. Constitution at dry dock in the Charlestown Navy Yard and wait for cannon fire to announce the setting of the sun.

-->Boston Sunset Sail -->

Experience a beautiful Boston Harbor sunset on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. Sailing offers a smooth and gentle experience on the water, which is great for having a romantic early evening out with that special someone. Our crew and captain offer top notch customer service to our guests.

-->Cocoa & Carols Holiday Cruise -->

Come aboard our luxury yacht Manhattan decked out in Holiday decor for an evening of holiday cheer. Enjoy a cruise out into Boston Harbor that is perfect for everyone in your family. Holiday favorites will fill the air to set the perfect mood for Holiday spirit.  This is Boston Holiday Cruise that is not to be missed. Cozy up with some hot cocoa, and treats for the whole family. Sit back, enjoy the view, the music, and the holiday cheer with this Boston Holiday Cruise.

-->Holiday Sunset Cruise -->

Step aboard the luxury yacht Manhattan decked out in Holiday decor for a Boston Harbor Holiday Sunset Cruise.  Our captain will provide light commentary of Boston Harbors sightseeing highlights. And enjoy light Holiday music as it will be played throughout the trip. Watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline.

-->Romantic Valentine’s Jazz & Champagne Cruise -->

Romantic Valentine’s Day Jazz & Champagne Tasting Cruise. Start or end your romantic evening with a light champagne tasting and stunning views of Boston. While sipping on your champagne, enjoy romantic jazz tunes by our house jazz band as we glide through the harbor. While fireworks are not included in this cruise, we hope to create metaphorical sparks for you and your date.

-->Evening Jazz Cruise -->

Grab that special guy or gal, or a couple of happy-footed friends who enjoy the sounds of music on our 90-minute live jazz cruise in Boston Harbor. Allow your senses to take you back in time with the sights of our 1920s styled New England Yacht combined with sounds of jazz. Our jazz cruise is preformed by Blue Motion Quartet, which brings a blend of vibrant modern groove with a standard jazz repertoire. Cruise through the harbor enjoying the City Lights as they dazzle on the waters of Boston Harbor, grab a glass of champagne or a mixed drink from the bar and dance with your sweetheart on this one of a kind cruise.  This is the perfect cruise for snuggling up with a loved one’s or dancing with a group of friends to the sounds of the Blue Motion Quartet. 

JOIN OUR MAILING LIST

Gift certificates, see our calendar of events, private charters.

Sail out from Rowes Wharf and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

• Private Yacht Charters
• Ticketed Cruises
• Schooners Adirondack III & IV
• Northern Lights
• Day Sails/Cruises
• Family Friendly
• Special Events
• Food Cruises
• Holiday Cruises
• Romantic Sails/Cruises
• Sightseeing Cruise
• Fireworks Cruises
• Harbor Cruises
• Press/Video
• Buy Tickets
• Contact / Directions
• Our Boston Location
• All Locations
• Information/Rates
• Around Town
• Places to Stay in Boston
• Places to Eat in Boston
• Things to Do in Boston
• General Information: 617-951-2460
• Purchase Tickets Now: 617-951-2460

Copyright © 2024 Classic Harbor Line, 60 Rowes Wharf, Boston, MA 02110 | Powered by Diedrich RPM.

Back to top