Sightseeing Day Sail around Boston Harbor
Recommended by 94% of travelers
Badge of Excellence
Boston, USA
- 1 hour 30 minutes to 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.
- Choice of several departure times to fit your schedule departures throughout the day
- Water cooler available to fill your reusable bottles
- Choose between from two duration lengths
- Card-only bar on board the boat serves wine, beer, and soft drinks
What's Included
- Duration: Choose between a 1.5 or 2 hour sailing experience
- This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
- 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)
Meeting and Pickup
Meeting point
- Classic Harbor Line Boston60 Rowes Wharf, Boston, MA 02110, USA
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.
End point
This activity ends back at the meeting point.Itinerary
Classic Harbor Line Boston MA Day Tours (Pass By)
Fan Pier (Pass By)
Boston Harbor Islands State Park (Pass By)
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Service animals allowed
- Near public transportation
- Most travelers can participate
- 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
- This tour/activity will have a maximum of 80 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Kathleen_S
We have a beautiful experience. The crew were helpful and engaging. Loved the time with friends. Enjoy your experience.
Reviews
4.8
based on 542 reviews
Rose_F, Oct 2025
Our afternoon was delightful- beautiful boat, gracious staff, absolutely recommend this tour!
Planning to bring my kids the next time.
April_Y, Oct 2025
It was wonderful. Great being out on the water and even better sailing. The crew was professional and so friendly. Loved the experience .
Sal_R, Oct 2025
It was a wonderful experience! The sloop held many passengers and we had smooth sailing. The experience of the staff was top notch. Explained the physics of a sailing ship, history of the area. Weather was great but then clouded up later.
Sandy_M, Oct 2025
Beautiful views, relaxing and enjoyable trip. The crew explained the ship and the rigging worked. Great crew!!!
Mark_P, Oct 2025
This was a great experience for me and my partner. Captain and crew were fantastic and knowledgeable.
Felice_K, Oct 2025
It was fascinating to watch a female captain and her crew sail the beautiful ship. Their knowledge of the surrounding area was top notch as well.
Jan_S, Oct 2025
We had great weather so the cruise in the harbor was relaxing and enjoyable. The crew was knowledgeable about different landmarks. We really enjoyed it for something different to do.
Timalynn_J, Oct 2025
Beautiful boat, friendly and knowledgeable crew, overall a wonderful experience that I highly recommend. We did the afternoon cruise and it was incredibly relaxing!
Brad_Y, Oct 2025
We had a great day! It was an impromptu team bonding opportunity, and the weather was perfect to be on the water. The crew was kind and informative, but let us have our own space and conversations, but there when you wanted them. The captain had been sailing this ship for 10 years and was a true pro. Unlike lots of sailboat excursions, the captain cut the motors and ran by sail for almost the entire trip. Loved it!
Kristian_A, Sep 2025
Great time on Boston Harbor. The sailing was great and we enjoyed watching the aircraft coming into Logan International.
Mary_E, Sep 2025
We lucked out on the weather and sailing was so relaxing and beautiful! The crew was really informative and we learned a lot of things about the islands and area in which we sailed. A wonderful experience!
Jaclyn_M, Sep 2025
The boat is so nice. The staff is great. The captain kept the boat as smooth as possible. Watching the planes come in was so cool as well.
Alexander_C, Sep 2025
First class experience. Friendly and very knowledgeable people. A real pleasure to see sailors doing what they love and sharing it with we, the fortunate tourists....
Therese_S, Sep 2025
The weather was not good, which, of course, no one has any control over.
However, the narration was so garbled. We couldn’t understand a word.
Response from Host, Oct 2025
Therese, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are sorry to hear that your trip was negatively impacted by the weather as well as the audio issues. We have very recently upgraded our sound system and are continuing to troubleshoot and adjust the settings to make sure the quality is as high as we can make it throughout the boat. We regret that this impacted your trip, and we will make it a priority to address your concerns. - Classic Harbor Line Boston
Chenxi_Z, Sep 2025
Very fun and chill experience. Crew members were so friendly and chill too! The sail was smooth and the weather is really nice on the water. Great view!
Paul_B, Sep 2025
Fantastic Schooner Sailing Trip around Boston Harbour.
Quality informative staff.
Well worth the extra money over your standard tour boat to Sail which was exhilarating.
Plenty to see & very reasonably priced drinks.
A perfect afternoon to end our Boston Holiday.
Kathleen_S, Sep 2025
We have a beautiful experience. The crew were helpful and engaging. Loved the time with friends. Enjoy your experience.
Yolanda_J, Sep 2025
We had a great time sailing around Boston Harbor today. The boat was lovely, the crew and captain were very friendly and the weather was fantastic!
VirginiaGinger_G, Sep 2025
Boat is lovely as were the crew. Sail "amongst the islands" is misleading as we never leave harbor and planes are taking off overhead throughout trip.
Corinne_B, Sep 2025
Was a very fun boat ride! The bartender Marcus was incredible he had great energy and made delicious drinks!
bret_b, Sep 2025
We learned some history and some local spots from the water. We also got some tips for restaurants and activities in the area. Good experience and beautiful views from the boat
James_H, Sep 2025
Fun and relaxing experience. We had a very good time. The captain was very friendly and courteous....
Fernanda_M, Sep 2025
Erick the captain was great and you can see he has lots of experience. Claire and Adam were very kind.
Bill_O, Sep 2025
This was a beautiful cruise around Boston harbor. The crew was great and very interactive with all of us. I highly recommend it.
Jo_D, Sep 2025
Very relaxing time on the bay. The two crew persons came around and talked with everyone, were knowledgeable with landmarks, and are helpful /personable. Drink prices very reasonable. Do not expect a navigated tour, but questions were always welcome. The captain (I wish I could remember her name) was quite skilled at her role and in navigating the sail boat 'the Adirondack?'. Great experience!
Fran_R, Sep 2025
So lovely, except captain and crew, had a blast - and I was solo. Great time aboard. Harbor splendid.
AnneMarie_P, Sep 2025
Incredible , staff was great and very professional and warm. Will definitely do again and would highly recommend!
Barbara_C, Sep 2025
It was wonderful! The crew was fabulous, so friendly and welcoming. The ride itself was thrilling and the views spectacular. I’ll definitely go again soon.
Stephanie_M, Sep 2025
The crew was wonderful. It was a beautiful day to be on the water and exploring the harbor. Highly recommend.
Jennifer_S, Sep 2025
Such a great and relaxing experience! The crew were friendly and helpful and the city view from the ship was outstanding!
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