Classic Tall Ship Cruise in Boston Harbor
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Escape the busy city streets and enjoy a relaxing day sail in Boston Harbor aboard a classic wooden schooner like Liberty Star or Fame. These charming tall ships provide an authentic sailing experience with plenty of deck space, fresh air, and stunning views of Boston’s skyline.
On select Sundays at 11am, join our Pastries & Prosecco sail aboard Liberty Star. This 2-hour cruise includes complimentary pastries and coffee from Flour Bakery, along with refreshing mimosas. It’s a perfect way to start your day with good company and great scenery.
While onboard, drinks are available for purchase—pay with cash, credit, or Apple Pay. Our menu features locally brewed beers, spirits from Boston distilleries, wine, soda, juice, and water. Feel free to bring your own snacks or a bagged lunch, but please no coolers or outside beverages.
There’s no formal narration during the daysails, but the captain and crew are happy to share stories about Boston’s landmarks and history if you ask. It’s a laid-back, informative way to see the city from a different perspective.
Frequently asked questions
How long is the sail?
The sail lasts between 1.5 to 2 hours, depending on the specific trip.
What’s included in the experience?
You’ll enjoy a classic tall ship sightseeing cruise in Boston Harbor, with plenty of space to relax and take in the views.
Can I buy drinks onboard?
Yes, drinks are available for purchase with cash, credit, or Apple Pay. The menu includes local beers, spirits, wine, soda, juice, and water.
Is the cruise suitable for children?
Absolutely. The experience is suitable for all ages, from infants to adults, and is accessible for all physical fitness levels.
Can I bring my own snacks?
Yes, you’re welcome to bring snacks or a bagged lunch. Just avoid coolers or outside beverages.
Is there narration during the sail?
There’s no formal narration, but the captain and crew are happy to answer questions and share insights about Boston’s landmarks.
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1.5 hours – 2 hours
Check availability to see start times.
Guided experience
Language options are confirmed when you check availability.
Key facts
What's included
Included
- Classic tall ship sightseeing cruise in Boston Harbor
Not included
- Gratuities (not expected but appreciated)
Itinerary
Enjoy a scenic sail in Boston Harbor aboard a classic schooner, with plenty of space for social distancing, fresh air, and sunshine. The 90-minute sail aboard Liberty Star offers a family-friendly way to see Boston from a new angle, away from busy streets. Learn about the city’s landmarks from the captain and crew or simply relax and soak in the views.
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Boston Harbor Sailing Adventure
Board one of our classic schooners for a relaxing day sail. Experience the city from the water, enjoy the breeze, and take in iconic sights as you cruise around Boston Harbor.
Meeting point & pickup
Meet at the starting point
Access the outer boarding dock via a gangway just to the right of Reel House Oyster Bar’s outdoor seating area. Please arrive 15-20 minutes before your scheduled sail time, as we depart promptly.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 0–1 day of departure
- May be canceled due to bad weather or insufficient bookings
Instant confirmation
Your booking is confirmed immediately after checkout.
From $39.55 per person
- Free cancellation
- Secure checkout with our booking partner
