Boston · TALL SHIPS, SCHOONERS & SAILING TRIPS
14 reviewed
The best tall ships, schooners & sailing trips in Boston sell out first, especially in summer and leaf season. These 14 are the standouts, with current prices and what sets each one apart, so you can lock a spot before the calendar fills.
Sail Boston Harbor on the Liberty Star tall ship. 90 minutes of skyline views, captain Q&A, and onboard drinks. Bring your lunch.
“Beautiful afternoon Great staff & captain Best view of Constitution Great refreshments at reasonable prices”
Sail the Salem Sound on the replica privateer schooner Fame. Help hoist sails, steer, and enjoy the cannon shot and harbor views.
“The people who ran the Fame and the event were friendly, knowledgeable, and personable. Very much enjoyed that it was a smaller group on board and it was a nice trip. If you choose, you can help hoist the sails and participate or you can just enjoy the ride!”
Classic Northern Lights sunset cruise in Boston Harbor with Fort Independence, inner-harbor views, and the USS Constitution cannon at dusk.
“The cruise was very nice. The food and drinks were good. But we have to wait for our food more time than we expected.”
Sail Boston Harbor on a replica pilot schooner with great crew Q&A, Seaport and island views, and a card-only bar for wine and beer.
“We have a beautiful experience. The crew were helpful and engaging. Loved the time with friends. Enjoy your experience.”
Sail Boston Harbor on a classic tall ship at sunset. Two hours, great views, and a galley bar for drinks, snacks, and photos.
“We had such a great time! Loved the experience! Would recommend to anyone! The drinks and atmosphere was wonderful and was inclusive for all ages.”
Sunset sail from Rowes Wharf on a classic Boston Harbor schooner, guided landmarks, skyline photos, and drinks you buy onboard.
“This experience was so relaxing and beautiful. The staff was so attentive it made for a perfect evening. Thank you.”
Classic schooner sail in Boston Harbor for 90 minutes, with skyline views and a chance to help raise sails. Drinks extra.
“This is a boat trip we take every time we visit Boston. Super relaxing and enjoyable. Weather was perfect as well.”
Classic schooner sailing on Boston Harbor with wind-in-your-hair views of Fan Pier, Inner Harbor Islands, Aquarium and more, 90-120 min.
“The schooner, Boston Harbor and most of all, the staff on the schooner Adjrondack II were absolutely lovely and so so knowledgeable. This is a MUST if you are spending a day or two in Boston! Thumbs up!!!!!”
Sail on a historic Salem schooner with real sailing, scenic bay views, and a drink bar, perfect for couples and special occasions.
“100% recommend. The view is amazing. We went pretty far, getting to see a lot of coast line. It was late October and nippy- so bring a jacket. I brought a beanie( Floridian).”
A 2-hour Boston Harbor sunset sail from Rowes Wharf on the Classic Harbor Line schooner with nonstop views, on-board drinks, and crew Q&A.
“Gorgeous seeing all of the islands around Boston. What a beautiful view of Boston’s lights from the water. Crew were great!”
A 2-hour Boston sunset tall ship cruise from Fan Pier. Hoist sails, steer a bit, buy drinks onboard, and see the skyline glow.
“We had a really great time! The staff were very friendly we enjoyed it very much.”
Sail the historic Schooner Fame in Salem. 100 minutes of hands-on deck fun, sea views, and onboard drinks for $39.
“Fantastic tour, we had a great time!! The Captain and crew were great, something very relaxing about cruising across the water with no engine noise!! My young daughter had a blast!!”
Sail Boston Harbor on a tall ship with coffee and pastries from Flour Bakery, plus mimosas available during the 2-hour ride.
“Fantastic excursion! Had such a relaxing ride around the harbor. Captain Fredo, Jess and Max made our trip so memorable. Highly recommend this excursion!”
Two-hour Boston Harbor tall-ship sail from Fan Pier with Flour Bakery pastries, tea/coffee, and included alcoholic drinks and Prosecco vibes.
“This was a thoroughly enjoyable sail. The Captain and crew (especially Freddo) were fun and easy going. I got to help Freddo hoist the topsail. The many pastries that made up the brunch were all fresh. The mimosas were cheap, plentiful and made island strength! I highly recommend this cruise and bunch of people.”
