Top Massachusetts Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

Only Show: Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Lunch Cruises | Sailing Trips | Sunset Cruises

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Boston Whale Watching Cruise

4.5 star rating: Recommended 449 Reviews

Looking for a whale watch that requires less travel time, offers the most comfortable ride available and gives you more time viewing some of the world's most ... 

Location: Boston, Massachusetts
Duration: 3 hours

From USD $55.65

Boston Duck Tour

5 star rating: Highly Recommended 478 Reviews

Water is no barrier for a duck, why should it be for you? A Boston Duck Tour is a wonderful way to get a great look at Boston on land and water. See all the ... 

Location: Boston, Massachusetts
Duration: 80 minutes

From USD $44.53

Boston Hop-on Hop-off Trolley Tour with Optional Harbor Cruise

4.5 star rating: Recommended 83 Reviews

Ride through the streets of Boston and take in the highlights with a convenient and easy hop-on hop-off trolley tour. Discover why this city is called the ... 

Location: Boston, Massachusetts
Duration: Flexible

From USD $31.00

Boston Historic Sightseeing Cruise

4 star rating: Recommended 24 Reviews

Whether you're visiting Boston for the first time, or a long time resident looking for a quick and relaxing getaway close to home, this trip around the harbor ... 

Location: Boston, Massachusetts
Duration: 90 minutes

From USD $30.39

Boston Odyssey Dinner Cruise

4.5 star rating: Recommended 32 Reviews

For the ultimate in elegance, you can't go past this three-hour dinner cruise on Boston's famous harbor. Enjoy fine dining, delicious wines, and entertainment ... 

Location: Boston, Massachusetts
Duration: 3 hours

From USD $104.67

Spirit of Boston Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 24 Reviews

See Boston’s waterfront sights from the deck of a luxury sunset dinner cruise. Enjoy a fabulous fine-dining buffet with a carving station and hit the dance ... 

Location: Boston, Massachusetts
Duration: Varies

From USD $99.43

Boston Super Saver: Whale-Watching Cruise Plus Admission to New England Aquarium

5 star rating: Highly Recommended 66 Reviews

Get up close and personal to New England’s wildlife with this Boston Super Saver. With your naturalist guide, spot whales and dolphins on a scenic 3-hour ... 

Location: Boston, Massachusetts
Duration: 3 hours

From USD $69.17

Boston Sunset Cruise

4.5 star rating: Recommended 55 Reviews

After a busy day sightseeing or working, what could be nicer than relaxing onboard one of Boston's finest boats for a cruise on the harbor? Watch the sun ... 

Location: Boston, Massachusetts
Duration: 90 minutes

From USD $31.44

Boston Sunset Cruise

5 star rating: Highly Recommended 1 Review

Enjoy a 90-minute cruise in Boston Harbor which heads out to Fort Independence located on Castled Island and named after George Washington. Then circles back ... 

Location: Boston, Massachusetts
Duration: 90 minutes

From USD $42.00

2.5-hour Boston Harbor Cruise with Brunch

Enjoy a delicious brunch and see historic sites along the harbor. This 2.5-hour brunch cruise will take you around the harbor with drinks available for ... 

Location: Boston, Massachusetts
Duration: 2 hours 30 minutes

From USD $73.50

Boston USS Constitution Cruise

4 star rating: Recommended 20 Reviews

Visit perhaps the most treasured of all Boston's landmarks, the USS Constitution. This 45 minute fully narrated tour brings you up close and personal with ... 

Location: Boston, Massachusetts
Duration: 45 minutes

From USD $24.10

Boston Odyssey Brunch Cruise

5 star rating: Highly Recommended 1 Review

Admire the unforgettable sights of Boston on board this breathtaking climate controlled yacht. This cruise offers the most unique brunch setting on Boston's ... 

Location: Boston, Massachusetts
Duration: 2 hours

From USD $82.40

Sunset Sail in Wellfleet

Set sail in time for the sunset on this 2.5-hour sailing experience. See Wellfleet from the water, take a turn at the helm, and watch the sun dip behind the ... 

Location: Wellfleet, Massachusetts
Duration: 2 hours 30 minutes

From USD $50.00

Private Jeremy Point Excursion from Wellfleet

Have the boat entirely to yourself as you go through the harbor to Jeremy Point on this private 3-hour sailing experience. Enjoy being on the boat and then ... 

Location: Wellfleet, Massachusetts
Duration: 3 hours

From USD $200.00

Fall on Cape Cod: Day Trip from Boston with Sightseeing Cruise

4 star rating: Recommended 92 Reviews

Autumn is a special time on Cape Cod, so enjoy it to the fullest on this luxury coach tour and scenic sightseeing cruise, affording amazing views of New ... 

Location: Boston, Massachusetts
Duration: 9 hours

From USD $80.00

5-Day Boston Tour: Cape Cod with Nantucket and Whale Watch

Take a multi-day Boston city tour featuring the financial district, seaport, Boston Common, Beacon Hill, and Quincy Market Place. Enjoy a fully narrated ... 

Location: Boston, Massachusetts
Duration: 5 days

From USD $1,059.00

Historical New England Harbor Cruise

Step aboard Yacht Northern Lights for a 2-hour sightseeing cruise to discover the history and mystery of our New England Harbor town, Boston. Boston Harbor is ... 

Location: Boston, Massachusetts
Duration: 2 hours

From USD $42.00

Private Sunset Sailing Experience in Wellfleet

Reserve the whole boat for a fantastic 2.5-hour private sunset sailing experience. Enjoy views of Wellfleet as you sail, take a turn at the helm, and admire ... 

Location: Wellfleet, Massachusetts
Duration: 2 hours 30 minutes

From USD $200.00

Jeremy Point Jaunt from Wellfleet Marina

5 star rating: Highly Recommended 2 Reviews

Cross the harbor to Jeremy Point on this 3-hour sailing experience. Enjoy the power of the wind as you move through the water to the secluded sand bar. Spend ... 

Location: Wellfleet, Massachusetts
Duration: 3 hours

From USD $50.00

Private Customized Cruise in Wellfleet

Customize your cruise for a unique sailing experience. For up to 6 hours, go where the wind takes you and explore Billingsgate Island or spend an afternoon on ... 

Location: Wellfleet, Massachusetts
Duration: Flexible

From USD $350.00

Spirit of Boston Lunch Cruise

4 star rating: Recommended 3 Reviews

Enjoy spectacular views of Boston as you dine on an all-you-can-eat lunch buffet aboard a scenic cruise. See an endless stream of city sights, including Bunker ... 

Location: Boston, Massachusetts
Duration: 2 hours

From USD $60.13

Cape Cod Summer Day Trip from Boston Including Sightseeing Cruise

4 star rating: Recommended 188 Reviews

On this New England summer adventure, escape from Boston for a day and journey to scenic Cape Cod, where sparkling beaches, lighthouses, cottages, ... 

Location: Boston, Massachusetts
Duration: 9 hours

From USD $78.00
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