SAILING WORLDWIDE
The best days on the water.
The 9 most popular boston tours. 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“A great experience! Saw 8-10 whales! The crew was friendly & I formative! A great day with my Navy sister❤️”
Sail Boston Harbor on a replica pilot schooner, passing Seaport District, Fan Pier, and islands like Spectacle and Long Island for $66.54.
“This was a great experience for me and my partner. Captain and crew were fantastic and knowledgeable.”
Sunset sailing on a classic tall ship from Boston’s Fan Pier with drinks for purchase and skyline views. Two hours for $68.
“Beautiful sail around the harbor. Definitely worth the time and money and great views and photo ops. Highly recommend sunset time.”
2-hour Boston Harbor sunset sail from Rowes Wharf on a classic schooner with skyline views and drinks for purchase. From $82.
“Such a beautiful evening with your incredible staff on the Boston sunset sail!!”
Sail Boston Harbor on a classic schooner from Fan Pier. Relax 90 minutes, enjoy skyline views, and choose onboard drinks.
“Captain Mark, John, and Carl were wonderful sailor hosts! Very personable and knowledgeable. They allowed our group to help hoist the sails, etc. It was a fun sailing tour of the harbor and doesn't hurt that it was a beautiful day. Definitely recommend this activity!”
Classic sailboat cruise on Boston Harbor with Adirondack III/IV. See Aquarium, Fish Pier and islands with crew Q&A.
“The crew was amazing and extremely knowledgeable!! We were just in a sail boat but they were explaining the different places/islands. The captain was friendly enough to let my partner sail the boat. Drinks and conversations were awesome! Thank you for making this trip amazing!”
Sail Boston Harbor on the Liberty Star from Fan Pier for $35, enjoy skyline views, and choose a weekend brunch add-on with mimosas.
“Along with the tour of the stadium, this was one of the entire groups favorite activities during our stay in Boston! Just the right amount of time. Crew was excellent! And thanks to Mother Nature, the weather was too.”
Sail Boston Harbor on a classic schooner for 1.5–2 hours, passing major landmarks like the Aquarium and Fan Pier. Soda included.
“This was such an unexpected treasure of a discovery in Boston! Besides having unseasonably beautiful weather for an October day, the sailing itself was terrific. Sails raised, light breeze once we motored out of the harbor and very peaceful. The crew was friendly and did not over narrate - they let us enjoy the day…”
Two-hour Boston Harbor sunset sail on a schooner from Rowes Wharf with skyline views, islands, and on-board drinks for purchase.
“Enhanced by beautiful weather and city scape. Energetic, polite and knowledgeable young staff Maybe up the drink selection??”
The sailing ports worth the trip, grouped by the sea they sit on.
