Boston


SAILING WORLDWIDE

9 Best Boston Tours 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.

9 Best Boston Tours 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

“INCREDIBLE experience!!! Highly recommend if you’re traveling to Boston - I went solo but would be so fun with friends/family too. After reading reviews about people getting seasick, I came prepared with motion sickness wristbands, an ear patch, and Dramamine just to be overly cautious. With all of that, I felt great the whole trip!…”

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

“This was a great experience for me and my partner. Captain and crew were fantastic and knowledgeable.”

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

/

5.Boston: Tall Ship Harbor Sail

Sail Boston Harbor on a classic schooner from Fan Pier. Relax 90 minutes, enjoy skyline views, and choose onboard drinks.

★ 4.6

“The overall experience was amazing. We often come to Boston with the family and are always looking forward for new fun things to do. This was so much fun that it will now become one of our standard activities. Amazing do yourself a favor and reserve a cruise.”

261 reviews1.5 hoursFrom $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

/
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

/
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

“It's hard to pick one thing. The crew were super nice, the boat was in beautiful shape, clean etc. The overall experience of being in such a big sail boat, seeing the crew raise the sails in an orderly fashion, feeling the angle of the ship as we were sailing into the wind, looking up…”

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

“It was a wonderful experience! The crew was very interactive with everyone and so accommodating! It was as if you had known them for a long time. I would highly recommend this excursion if you ever visit Boston.”

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