Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail pas

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families and friends who want to sail and see the sights of Boston from the water! Within minutes of leaving the dock, guests will forget the distractions of life on land and experience the joy of a leisurely sail. Sit back and relax as the crew raises sail and provides beverage service. Drinks are available for purchase by credit card only. Guests are welcome to bring a picnic onboard. The knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer.

From: $0.00

Location: Boston

What's Included

Community Discussion

Q&A

Q: Can I bring my kids on the sailing trip?

A: Yes, this sailing trip is great for families! There’s no strict age limit, but keep in mind that you should supervise younger kids. The crew is friendly, and it’s a nice way for kids to see the landmarks from the water. Just make sure to bring hats and sunscreen for the little ones!

Q: What happens if the weather is bad on the day of the sail?

A: If the weather looks bad, the crew will usually reach out to you about rescheduling or canceling. They prioritize safety, so don’t worry if it gets canceled; you can always book another day! Just check your email or call them a few hours before if you're unsure.

Q: Is there parking available near the dock?

A: Yes, there is parking available near the dock! There are several lots in the area, but they can fill up fast, especially on weekends. I recommend getting there early or checking out the nearby street parking options. You can also use a rideshare service if you want to avoid parking hassle!

Discussions

Thinking of booking the Boston Harbor day sail for my partner's birthday!

Hey everyone! I’m planning to surprise my partner with the 2-hour sightseeing day sail around Boston Harbor. I’ve heard amazing things about the Adirondack schooners. I love the idea of bringing a picnic onboard, but I’m wondering what kind of drinks I should bring? Also, do they have options for non-alcoholic drinks on the boat? Any tips would be super helpful!

Just got back from the Boston Harbor sail and it was incredible!

Wow, I just experienced the 1.5-hour sail around Boston Harbor, and it was such a relaxing trip! The views were stunning, especially of Castle Island. The crew was super friendly and even shared some cool history tidbits. I brought a small picnic, and it was the perfect way to enjoy the day on the water. Highly recommend it for anyone looking for a chill outing in Boston!