Boston Sailing Trips


SAILING WORLDWIDE

9 Best Boston Sailing Trips 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.

9 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

/

1.City Cruises Boston Whale Watching Cruise by High-Speed Boat

High-speed Boston whale watching to Stellwagen Bank with naturalist narration, indoor comfort, and strong odds for whales and dolphins.

Most Popular★ 4.5

“The whale watching tour was okay but not really worth the money. While we did see some whales, there were way too many people on board, which made it hard to get a good view. The constant movement of people going in and out from the deck to indoors was also a bit frustrating. That…”

3,115 reviews3 hours 30 minutes (approx.)From $85.56by Boston Harbor City Cruises

Check Availability →Read the review →

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.”

541 reviews1 hour 30 minutes to 2 hours (approx.)From $66.54by Classic Harbor Line - Boston

Check Availability →Read the review →

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

/
Boston: Harbor Champagne Sunset Sail from Rowes Wharf - The 2-hour harbor route: Fish Pier, Fan Pier, and the skyline frame
Boston, Boston Sailing Trips, Cruises & Boat Tours, Evening Experiences, Marina & Harbor Cruises, Sunset Sails, Tour Reviews, Wine Tours

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

/
Boston: Tall Ship Harbor Sail - Getting to Fan Pier Marina without stress (and finding your ship fast)
Boston, Boston Sailing Trips, Cruises & Boat Tours, Marina & Harbor Cruises, Tall Ships & Sailing Boats, Tour Reviews

Boston: Tall Ship Harbor Sail

/
Boston: Downtown Harbor Sailing Cruise - The Route: Fish Pier, Fan Pier Court Landmark, Castle Island, and Beyond
Boston, Boston Sailing Trips, Cruises & Boat Tours, Marina & Harbor Cruises, Sailing, Tour Reviews

Boston: Downtown Harbor Sailing Cruise

/
Boston: Tall Ship Harbor Sail with Weekend Brunch Option - What you’ll see on the Boston Harbor schooner cruise
Boston, Boston Sailing Trips, Cruises & Boat Tours, Marina & Harbor Cruises, Tall Ships & Sailing Boats, Tour Reviews

Boston: Tall Ship Harbor Sail with Weekend Brunch Option

/

7.Boston: Tall Ship Harbor Sail with Weekend Brunch Option

Sail Boston Harbor on the Liberty Star from Fan Pier for $35, enjoy skyline views, and choose a weekend brunch add-on with mimosas.

★ 4.5

“We are from Texas and came to Boston for the lacrosse playoffs and we were looking for something to do. When I tell you this experience was sooooo great, I mean it! If you’re looking for something to do, this is it. All crew members were nice, smiling, hard working. Although the wind wasn’t cooperating…”

220 reviewsFrom $35by Liberty Fleet of Tall Ships

Check Availability →Read the review →

Boston: Downtown Harbor Sailing Cruise - The Route: Fish Pier, Fan Pier Court Landmark, Castle Island, and Beyond
Boston, Boston Sailing Trips, Cruises & Boat Tours, Marina & Harbor Cruises, Sailing, Tour Reviews

Boston: Downtown Harbor Sailing Cruise

/

8.Boston: Downtown Harbor Sailing Cruise

Sail Boston Harbor on a classic schooner for 1.5–2 hours, passing major landmarks like the Aquarium and Fan Pier. Soda included.

★ 4.7

“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…”

202 reviewsFrom $67by Classic Harbor Line Boston

Check Availability →Read the review →

Boston Harbor Sunset Sail Tour - Seaport District Views and Fan Pier Landmarks From the Water
Boston, Boston Sailing Trips, Cruises & Boat Tours, Evening Experiences, Marina & Harbor Cruises, Sunset Sails, Tour Reviews, Tours

Boston Harbor Sunset Sail Tour

/

9.Boston Harbor Sunset Sail Tour

Two-hour Boston Harbor sunset sail on a schooner from Rowes Wharf with skyline views, islands, and on-board drinks for purchase.

★ 5.0

“This sunset sail was PERFECT. The crew was awesome. Honestly, what more is there to say? It was a great experience. Highly recommend for date night or a chill evening out!”

132 reviews2 hours (approx.)From $82.27by Classic Harbor Line - Boston

Check Availability →Read the review →

Scroll to Top

Explore by Destination

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

The Mediterranean

The Atlantic Isles

The Gulf

The Caribbean

The Pacific