Sightseeing Day Sail around Boston Harbor
4.7
251 Ratings
Boston
Duration: 2 hours
Cancellation: 1 day learn more
What's Included
  • Duration: Choose between a 1.5 or 2 hour sailing experience
What's Not Included
  • Beverages are not included, but are available for purchase by credit card only.
  • Gratuities (recommended for the captain and crew)
Additional Information

Pick from a 1.5 or 2-hour sail across Boston Harbor on the stunning Adirondack III schooner, a 80-foot pilot schooner reminiscent of the 1890s. Cruise past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island featuring its Long Island Head Light. Ideal for families and groups of friends eager to explore Boston’s sights via the sea!

Immediately after departing the dock, guests can leave behind their terrestrial worries and enjoy the calming experience of a relaxed sail. Let the crew take care of hoisting the sails and serving drinks. Please note, drinks can only be purchased with a credit card. We encourage you to bring your picnic onboard.

Our captain and crew are knowledgeable about Boston Harbor and its nearby areas, always ready to answer any queries about the area’s sights and history. From intriguing trivia to age-old legends, the seafaring heritage of Boston has a wealth of fascinating stories to share.

  • 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.
Location
Classic Harbor Line Boston
Rowes Wharf
The boat departs from Rowes Wharf, directly behind the Boston Harbor Hotel, located at (for GPS) 400 Atlantic Avenue, Boston (02110). Check-in at Rowes Wharf is located in the Ferry Terminal, a climate controlled public space, located on the wharf only steps away from our dock. If guests are lost or running late, please call us at 617-951-2460.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(251 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Jessicalebe
Jun 12, 2024
Recommend! - So relaxing sailing around the harbor. The captain and staff were so nice and knowledgeable. The crew were also awesome bartenders. It’s a laid back tour, they don’t announce landmarks but are very willing to talk
Review provided by Tripadvisor
Bsczn
Jun 8, 2024
Delightful sail - We particularly enjoyed talking with our captain on Adirondack III on May 29. She was terrific! Delightful and relaxing sail.
Review provided by Tripadvisor
Mila_p
Jun 2, 2024
A perfect evening sail! - We sailed with our son and young grandchildren. The crew was incredible: friendly, capable, and informative with us and kind and attentive to the children’s needs. The ship was beautiful and the evening sail exquisite—Couldn’t ask for more!! Thanks!!
Review provided by Viator
Lizzy_s
Jun 1, 2024
Worth the money - Nice experience and friendly crew. It was worth the price and drinks were available for an additional fee.
Review provided by Viator
Bianca_g
May 27, 2024
Fantastic experience and... - Fantastic experience and crew members provided great service! Sail boat was beautiful and clean. Two hrs was a perfect time for this excursion.
Review provided by Viator
Michael_r
May 27, 2024
Boston Harbor on the Adirondack III - Enjoyed the time on the sailboat. It was fun and good time to relax and enjoy the harbor breeze and views
Review provided by Viator
Tritzy69
May 26, 2024
Fabulous sail around the harbour - Had a great 1 1/2 sail around the harbour, nice friendly experienced crew. Always take an extra warm top as its chilly even when its 72 degrees on shore. Well worth the experience, small group so great.
Review provided by Tripadvisor
J8994utangieg
May 26, 2024
The views! - Wonderful crew. Great views of the skyline and a little history thrown in for good measure. I would definitely recommend this tour.
Review provided by Tripadvisor
Diana_m
May 26, 2024
Beautiful Sail - This was even better than anticipated! Crew was great, we had perfect weather and they really took us sailing! We loved it because it was low key, not a huge group of people and you could just enjoy the sights and sounds without a tour guide talking constantly. If you are queasy or unsteady sit in the back on the cushions, because we got going in the wind which felt amazing!
Review provided by Viator
Kay-cee-1138
Jun 9, 2024
A nice introduction to Boston Harbor - Although the Wednesday was cold and wet, we still enjoyed the one and half hour sailing trip out to the outer part of Boston Harbor. It provided a good perspective from the water of many of the landmarks, such as the skyline, Port of Boston, Castle Island and a few of the closer harbor islands. The small sailing ship motored out of the Inner Harbor before setting its sails for a quiet and contemplative trip. The crew was friendly and professional, and when they were not working the sails, they mixed with the passengers, answered questions, and pointed out sights. It appeared that those passengers seated toward the stern closest to where the captain remained at the wheel may have had the benefit of running commentary by him. Buying tickets for the sailing voyage online seemed much harder than it should have been. And we found that we needed to go by the Classic Harbor Line office by Rowes Wharf beforehand to check in and pick up actual boarding passes. But it all worked out fine. The trip started at 2:30 pm and returned at about 4 pm. By then, rush hour was in progress, so we just made our way up to a North End restaurant for a couple of hours before trying to get out of the city. All in all, a nice afternoon's experience.
Review provided by Tripadvisor
Select Date and Tickets
up to 8 guests
1 Adult
June 2024
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Today