SAILING WORLDWIDE
The best days on the water.
The 9 most popular boston sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
High-speed Boston whale watching to Stellwagen Bank with naturalist narration, indoor comfort, and strong odds for whales and dolphins.
Most Popular“This was an incredible experience!!! Saw many whales swimming and flapping their fins! The crew was fantastic at pointing out animals.”
Sail Boston Harbor on a replica pilot schooner, passing Seaport District, Fan Pier, and islands like Spectacle and Long Island for $66.54.
“Beautiful views, relaxing and enjoyable trip. The crew explained the ship and the rigging worked. Great crew!!!”
Sunset sailing on a classic tall ship from Boston’s Fan Pier with drinks for purchase and skyline views. Two hours for $68.
“Started out quite warm but as the sun set it became breezy and very pleasant. We let some interesting people to talk to and enjoyed the drinks.”
2-hour Boston Harbor sunset sail from Rowes Wharf on a classic schooner with skyline views and drinks for purchase. From $82.
“A lot of fun! The crew was very helpful and attentive. The sunset was beautiful and peaceful”
Sail Boston Harbor on a classic schooner from Fan Pier. Relax 90 minutes, enjoy skyline views, and choose onboard drinks.
“Excellent experience on a tall mast Ship. Captain and Crew were fantastic.”
Classic sailboat cruise on Boston Harbor with Adirondack III/IV. See Aquarium, Fish Pier and islands with crew Q&A.
“Great boat, crew, weather, sights and beverages so what’s not to like?!. Great experience”
Sail Boston Harbor on the Liberty Star from Fan Pier for $35, enjoy skyline views, and choose a weekend brunch add-on with mimosas.
“My sister and I loved this sailing trip around the Boston Harbor. The captain is an experienced sailor as well as an actor. He's quite the entertainer! Funny! The rest of the crew is helpful and accommodating. The sail is relaxing, interesting, and an interesting way to enjoy Boston. I would do it all over…”
Sail Boston Harbor on a classic schooner for 1.5–2 hours, passing major landmarks like the Aquarium and Fan Pier. Soda included.
“Great crew….. very attentive to the guests. The captain was fabulous nice sail through the Boston Harbor.”
Two-hour Boston Harbor sunset sail on a schooner from Rowes Wharf with skyline views, islands, and on-board drinks for purchase.
“Beautiful cruise in the harbor. Great backdrop of the city at sunset and planes landing over your head. Great and helpful staff.”
The sailing ports worth the trip, grouped by the sea they sit on.
