Overview
Available languages
Mobile ticket
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.
Additional Info
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
Children must be accompanied by an adult
Minimum drinking age is 21 years. Coolers and outside alcoholic beverages are not permitted
Dress for the weather - it's often cooler on the water
Please let us know in advance if assistance is required for boarding
Only animals that perform a manual task to assist a person are permitted aboard. Emotional support animals and pets are not permitted
Plan to arrive at the ticket booth 15-30 minutes prior to the departure time. The meeting point is located directly behind the Boston Harbor Hotel in the Ferry Terminal just steps away from the dock. Boarding begins 5 minutes prior to the scheduled departure time.
This experience will be aboard Schooner Adirondack III or Schooner Adirondack IV
Large group bookings are not permitted. Multiple bookings are subject to added fees or cancellation by operator
What To Expect
Classic Harbor Line Boston MA Day Tours
Sail around Boston's Seaport District and take in views of many newly constructed buildings along with some classic structures that originally comprised Boston's waterfront community
Fan Pier
Sail by Fan Pier and see the spanning Moakley Federal Courthouse, the World Trade Center and Harpoon Brewery.
Options
Sail Boston® 250 Option
Aboard an Adirondack Schooner: Sail with us for Sail Boston® 250 aboard one of our classic Adirondack Schooners to see the visiting boats in Boston Duration: 1 hour 30 minutes: Sail Boston Harbor on a classic sailboat offering panoramic views of visiting ships. A great sightseeing experience! Drinks available for purchase: Drinks are available for purchase by credit card. Food is not available.
Oyster Sail Option
Must be 21+ to attend: Select this option to sail aboard one of our Adirondack Schooners with Oysters included. Duration: 2 hours Oysters : Enjoy a curated selection of local oysters, shucked on board and paired with mignonette, lemon, and hot sauce. Drinks available for purchase : Drinks are not included but available for purchase onboard.
2-hr Peak Day Sail
Duration: 2 hours Aboard Adirondack II or III
1.5-hr Peak Day Sail
Aboard Adirondack II or III: Peak rates apply.
1.5-hr Off Peak Day Sail
Aboard Adirondack II or III
2-hr Off Peak Day Sail
Aboard Adirondack II or III
What‘s Included
This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
Duration: Choose between a 1.5 or 2 hour sailing experience
Beverages are not included, but are available for purchase by credit card only.
Gratuities (recommended for the captain and crew)
Food (guests are welcome to bring their own snack aboard)
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
568 reviews
Total reviews and rating from Viator & Tripadvisor
Highly recommend
Jfarrg,Jun 10, 2026
- Review from Tripadvisor
5.00Wonderful experience with the captain and energetic crew. Beautiful day to sail the Boston harbor.
Very cool experience
crystal r,Jun 8, 2026
- Review from Viator
5.00First of all I have never been on a sail boat before it was incredible to watch the crew manage the sails and keep us moving along at quite a clip. Also almost as impressive was how they managed to keep us all topped up on drinks at the same time. It was a very cool experience and I'm very glad I did it. Well worth it and I would definitely recommend if your looking for something a little different to do while your in the city.
Fantastic Sail
Alzenau1,Jun 5, 2026
- Review from Tripadvisor
5.00What a fantastic experience to enjoy the beauty of Boston from the Water on a quiet sailboat with such wonderful staff thank you Charlie, claire and great team and really felt a positive vibe. We were also very lucky that we had supreme weather however, with this crew, we would’ve had a great timeif it were raining thank you.
Great trip!
Steve J,Jun 5, 2026
- Review from Viator
5.00Wonderful tour of the harbor. Great crew and a very nice afternoon. Gavin’s my Drinks onboard was a nice touch as well. Just a very nice relaxing cruise.
Fun trip around the...
Brenda M,Jun 1, 2026
- Review from Viator
5.00Fun trip around the Harbor. Not crowded and the staff was very knowledgeable. Eric the captain was great!
welcomed pleasure
richardoP6645RT,May 29, 2026
- Review from Tripadvisor
5.00Our sail on the Adirondack II was amazing. Our Captain, Dante & crew were very friendly and helpful. Sailing was a new experience for me & I'm looking forward to doing it again. I appreciate the knowledge & skill of the crew as they were able to handle the boat and sails with expertise. It was a wonderful experience to be a passenger taking in the beautiful views of the harbor & relaxing with a cold beverage. We will definitely be doing this again. Great Job! Rich & Karen
Sailing Boston harbor and beyond
Susanm1ack,May 28, 2026
- Review from Tripadvisor
5.00Very relaxing. Staff knew what they were doing and imparted interesting info about what we were seeing. would have been nice for one person with a microphone to tell us what we were seeing. Other staff just talked to the people they were near and no one else could hear.
Wonderful sailing tour of...
Timothy J,May 24, 2026
- Review from Viator
5.00Wonderful sailing tour of Boston Harbor. Very cool way to see the harbor. The Adirondak II crew was informative, welcoming and attentive. Though the tour was not narrated, the crew was great at pointing highlights, names of the harbor islands and their histories.
Don't think twice :D
Ashley D,May 23, 2026
- Review from Viator
5.00We had a great time and highly recommend! We were a group of six and had the best afternoon; the crew was friendly, knowledgeable and attentive. The boat is gorgeous and on a beautiful day, there's no way to beat it.
A very nice sail.
jihanshareef,May 21, 2026
- Review from Viator
5.00The captain was incredible. Crew was awesome. They provided blankets which came in handy because it was a chilly day. You won’t be sorry if you book them.
Related Experiences
Operated by Classic Harbor Line - Boston