Boston Sailing Trips


SAILING WORLDWIDE

3 Best Boston Sailing Trips Worldwide

The best days on the water.

The 3 most popular boston sailing trips. What each sail costs, how long you are on the water, and which crews run it well.

3 Best Boston Sailing Trips Worldwide

City Cruises Boston Whale Watching Cruise by High-Speed Boat - The Naturalist Factor: How You Go From Spotting Shapes to Real Identifying
Boston, Boston Sailing Trips, City Tours, Cruises & Boat Tours, Dolphin & Whale Sails, Tour Reviews, Whale Watching

City Cruises Boston Whale Watching Cruise by High-Speed Boat

Sightseeing Day Sail around Boston Harbor - Price and value: is $66.54 a fair deal?
Boston, Boston Sailing Trips, Cruises & Boat Tours, Marina & Harbor Cruises, Tour Reviews

Sightseeing Day Sail around Boston Harbor

2.Sightseeing Day Sail around Boston Harbor

Sail Boston Harbor on a replica pilot schooner, passing Seaport District, Fan Pier, and islands like Spectacle and Long Island for $66.54.

5.0

“The boat is so nice. The staff is great. The captain kept the boat as smooth as possible. Watching the planes come in was so cool as well.”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor - What 2 hours on the harbor actually feels like
Boston, Boston Sailing Trips, Cruises & Boat Tours, Evening Experiences, Marina & Harbor Cruises, Sailing, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

3.Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Sunset sailing on a classic tall ship from Boston’s Fan Pier with drinks for purchase and skyline views. Two hours for $68.

4.5

“It is a very authentic experience. I felt like a pirate. The ship is relatively small, so it never got too crowded. Some guests even learned the ropes and helped to release the sails. The passing by of other tall ship and they “fighting” each other with water cannons was the cherry top.”

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Explore by Destination

The sailing ports worth the trip, grouped by the sea they sit on.