Category New England Sailing and Schooner Tours

Boston · NEW ENGLAND SAILING AND SCHOONER TOURS

Top 15 Boston Sailing and Schooner Trips

23 tours

Tall ships still work this harbor, and an hour under canvas beats an hour behind glass. The 15 best sailing trips are below, with boat sizes, sailing windows, prices, and which ones pour something while the sun drops.

Classic Tall Ship Cruise in Boston Harbor

Classic Tall Ship Cruise in Boston Harbor - The 90-minute itinerary: what happens once you leave the dock

1.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35Our pick

Sail Boston Harbor on a classic schooner for about 90 minutes, with crew-led fun, skyline views, and optional onboard food and drinks.

“Sailing with Captain Fredo and his crew on Boston Harbor was an excellent experience. The boat was clean, well-maintained, and comfortable. Captain Fredo demonstrated great knowledge of the harbor and navigated confidently, which made the trip smooth and enjoyable. The crew was attentive and professional, ensuring that everything ran efficiently without being intrusive. The views of the Boston skyline from the water provided a unique perspective of the city, making it a memorable outing. I would recommend this cruise to anyone looking for a relaxed and well-organized sail in Boston Harbor.”

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Schooner Fame Sailing Tour

Schooner Fame Sailing Tour - The Main Sail Off Salem Sound, Marblehead, and Beverly

2.Schooner Fame Sailing Tour

★★★★★★★★★★5.0 · 571 reviews · 1 hour 40 minutes (approx.) · from $50Top rated

Sail off Salem on the Fame, a hands-on privateer-style schooner cruise with sail-raising, steering time, cannon fire, and Salem Sound stories.

“Beautiful boat and a kind friendly crew. My daughter and I loved the sunset sail. Would do it again and again.”

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Boston: Harbor Sunset Yacht Cruise

Boston: Harbor Sunset Yacht Cruise - Rowes Wharf meeting point, and how to find the dock without stress

3.Harbor Sunset Yacht Cruise

★★★★★★★★★★4.6 · 570 reviews · 2 hours · from $54

Boston Harbor sunset on the Northern Lights yacht, with Fort Independence views, light commentary and music, plus a USS Constitution cannon at sunset.

“My group had a 2nd great experience on the cruise. The boat is classy and the team serving all of us was fantastic.”

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Sightseeing Day Sail around Boston Harbor

Sightseeing Day Sail around Boston Harbor - Schooner Adirondack III or IV: what sailing feels like on the water

4.Sightseeing Day Sail around Boston Harbor

★★★★★★★★★★5.0 · 541 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $66

Sail Boston Harbor on a replica pilot schooner. Pick 1.5 or 2 hours, enjoy sea views, Q&A with crew, and card-only drinks.

“Was a very fun boat ride! The bartender Marcus was incredible he had great energy and made delicious drinks!”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Meeting point at Fan Pier: how to avoid a stressful start

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

Boston: Harbor Champagne Sunset Sail from Rowes Wharf - A Classic Schooner at Sunset: Why the 2 Hours Feel Long (In a Good Way)

6.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Boston Harbor sunset sail from Rowes Wharf on a classic schooner. See the skyline, islands, and Navy Yard, with drinks for purchase.

“Therese was absolutely brilliant, we had an absolutely fantastic time on the cruise and would 100% go again. You have to buy drinks on board (no included) but we knew that before and it was still so worth it!”

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Boston: Tall Ship Harbor Sail

Boston: Tall Ship Harbor Sail - The 90 minutes: exactly long enough for a reset

7.Tall Ship Harbor Sail

★★★★★★★★★★4.6 · 261 reviews · 1h 30m · from $35

Sail Boston Harbor on a classic schooner from Fan Pier. 90 minutes of skyline views, hands-on sails, and onboard beer or wine.

“fabulous experience! I got to help hoist the sales. Ride was smooth and fun.”

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Boston: Downtown Harbor Sailing Cruise

Boston: Downtown Harbor Sailing Cruise - What the 90 minutes to 2 hours route looks like

8.Downtown Harbor Sailing Cruise

★★★★★★★★★★4.8 · 227 reviews · 90 minutes - 2 hours · from $66

Sail Boston Harbor on Adirondack III or IV for 90 minutes to 2 hours, past islands and landmarks. Drinks available, soda and water included.

“Great boat, crew, weather, sights and beverages so what’s not to like?!. Great experience”

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Sailing on Historic Schooner Yacht in Salem, MA

Sailing on Historic Schooner Yacht in Salem, MA - Your 2-hour sailing game plan on the bay

9.Sailing on Historic Schooner Yacht in Salem, MA

★★★★★★★★★★5.0 · 172 reviews · 2 hours (approx.)

A 2-hour sunset schooner sail in Salem Sound with real sails, ocean views, and optional sail work plus a full onboard bar.

“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).”

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Newport Afternoon Sightseeing Sail on Classic Sailboat

Newport Afternoon Sightseeing Sail on Classic Sailboat - Bowen’s Wharf logistics: how to show up and not stress

Boston Harbor Sunset Sail Tour

Boston Harbor Sunset Sail Tour - Getting On Board at Classic Harbor Line, 60 Rowes Wharf

11.Boston Harbor Sunset Sail Tour

★★★★★★★★★★5.0 · 132 reviews · 2 hours (approx.) · from $82

Boston Harbor sunset sail with Classic Harbor Line past Seaport, Fan Pier, islands, and Castle Island. Two hours, crew Q and A, drinks.

“The staff was AMAZING! And the experience was perfect! It felt peaceful, relaxing, family oriented and provided a chance to connect with lovely people in a gorgeous setting. Would repeat this and recommend.”

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Newport: Day Sail on Narragansett Bay aboard Aquidneck

Newport: Day Sail on Narragansett Bay aboard Aquidneck - Bowen’s Wharf meet-up: where to go and how to get there on foot

12.Newport: Day Sail on Narragansett Bay aboard Aquidneck

★★★★★★★★★★4.8 · 117 reviews · from $53

Sail Aquidneck through Newport Harbor and Narragansett Bay, past Pell Bridge and Ocean Drive, with crew commentary and soft drinks.

“This was my first Sailboat experience. Staff was very courteous, comforting and professional. Regular historically updates with some refreshments available onboard was something different to other regular boat rides. Kids liked the ride and overall, it was a memorable experience.”

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Boston: Sunset Tall Ship Harbor Cruise

Boston: Sunset Tall Ship Harbor Cruise - Getting to Fan Pier Marina, and finding your ship fast

13.Sunset Tall Ship Harbor Cruise

★★★★★★★★★★4.8 · 115 reviews · 2 hours · from $68

Sail into Boston Harbor at sunset on a classic tall ship. Help hoist sails, steer a bit, and enjoy skyline views for 2 hours.

“Great views of Boston from the water. Interesting experience to be on a tall ship rather than a modern vessel.”

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Luxury Catamaran Sailing Charters in Maine

Luxury Catamaran Sailing Charters in Maine - Captain Nils, Nick, and the best place to hear the story

14.Luxury Catamaran Sailing Charters in Maine

★★★★★★★★★★5.0 · 85 reviews · from $135

2-hour catamaran sail from Saco with Captain Nils, lighthouses, wildlife spotting, and a small group. Bring snacks for easy comfort.

“Terrific morning with friends. The captain and crew were welcoming and knowledgeable. The cat is terrific. We went out on the ocean and then on the river. Highly recommend it.”

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Salem: Historic Schooner Sailing Cruise

Salem: Historic Schooner Sailing Cruise - Getting Onboard at Pickering Wharf Marina, Then Settling In

15.Salem: Historic Schooner Sailing Cruise

★★★★★★★★★★4.9 · 84 reviews · from $39

Sail the historic Schooner Fame in Salem Sound, a 100-minute gaff-rig cruise with hands-on fun, bar drinks, and big views from Pickering Wharf.

“It was a beautiful and relaxing trip. The Captain and crew were wonderful, very personable and knowledgeable. It was a great trip. Thank you.”

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