Key Points on this Boston sailboat tour:
- This Sail Boston 250 sailboat ride is 1.5hrs long.
- Tickets on the afternoon day sail in Boston are up to $68.90 per person.
- You’re Not Just Watching — You’re Sailing: Unlike a traditional harbor cruise, you’ll feel the schooner heel gently under the breeze, trim the sails, and move in rhythm with the fleet — becoming part of the maritime spectacle itself.
- Unobstructed, Open-Air Views: Adirondack’s classic deck design keeps every seat close to the water and the action. From your spot on deck, you’ll have panoramic views of Boston’s skyline and the international tall ships sailing nearby.
- Skip the Crowds: Leave the congested waterfront behind and join a smaller, more personal voyage on the harbor. There’s no better way to see the ships than from the water — under sail, in peace.
- Comfort and Charm: Adirondack is a 65-foot wooden schooner, built in the spirit of the 1890s racing yachts — fast, graceful, and comfortable. She’s known for smooth sailing and plenty of room for relaxation.
- Drinks on Deck: A full bar offering beer, wine, and soft drinks is available for purchase, so you can toast to the international gathering as you sail among it.
- On this day cruise in Boston we will be shutting off our engines and setting sail for as much as possible.
Highlights of this Boston sail boat tour
- Sail Boston® 2026 (July 11–16, 2026) marks Boston’s participation in the global Sail250® celebration — honoring 250 years of American history and seamanship. The harbor will welcome an extraordinary fleet of tall ships and naval vessels from around the world for one of the most impressive maritime events in the nation.
- During our Boston Harbor cruises, we will sail as close as we can to some of these historic vessels:
- * Amerigo Vespucci – Italy
* Bluenose II – Canada
* Cisne Branco – Brazil
* Juan Sebastián de Elcano – Spain
* Esmeralda – Chile
* Dar Młodzieży – Poland
* Denis Sullivan – USA - Authentic Sailing Adventure: Glide silently under sail among the international fleet — an experience few will ever have.
- Best Photo Opportunities: Capture the tall ships’ masts, rigging, and flags from sea level as you move among them.
- Exclusive and Intimate: Smaller passenger count means a relaxed, friendly atmosphere and personalized experience.
- No Engines, No Crowds, No Stress: Just the sound of wind, water, and canvas — and front-row views of one of the greatest maritime celebrations in the world.
What is Not Included
- Our day cruises in Boston do not include food. Feel free to bring your own picnic!
- The price of drinks is not included in the cost of your ticket – please bring a credit card to purchase on board.
- Credit Cards are the only form of payment accepted on your cruise. Please plan accordingly.
- Please bring valid identification with you. Identification is checked prior to boarding for guests interested in an adult beverage.
- Gratuity is not included in the price of your sail.
- Beverages and Coolers: Outside adult beverages and coolers are not allowed aboard.
- We reserve the right to add a 15% gratuity for parties of 12 people or more, regardless of whether they are booked together or not.
Meeting Location
- 60 Rowes Wharf, Boston, MA
- Upon arrival at our location please check–in with our ticket representative inside the ferry terminal to receive boarding passes.
Are you a group of 10 or more?
Call us directly at (617) 951-2460.
FAQs
Reviews
- Great team building day
We took our sales team out for a day sail as a team building event. Everyone who came told us what a great day they had and asked us to run another event on the boat!
– chrisfeazel
- Great Sail!
Had a fabulous couple of hours aboard the Adirondeck III on Saturday afternoon. The crew was courteous, very helpful and friendly. The captain provided some great trivia about the Harbor Islands.
– LynnAaronson
- What a fab day to spend the afternoon – book now!
Had a friend in town and took her out for a Friday afternoon sail for her birthday. The crew was very friendly and hospitable. They were also very knowledgeable on the skyline and the history. I would highly recommend to anyone and would personally go again – given the chance!
– megonthemove
- Perfect end to a great vacation
We enjoyed this relaxing sailboat ride and beautiful scenery! The staff is very friendly and informative regarding every aspect of the trip from what we are seeing to how the boat works and any other question we had….loved it!!
– Mandyjordan
- Excellent harbor cruise aboard a lovely schooner
Really enjoyed this experience! The crew was very friendly and knowledgeable. The cruise itself was delightful. 2 hours was a really good duration. Very relaxing. Great that we were able to purchase beverages on board and all non-alcoholic drinks were complimentary. Wonderful views of the harbor on a very nice sunny day. I would definitely do this again with any and all out-of-town guests that want to see more of Boston.
– alenzcrafter
- Great Time!
The weather was excellent, as the craft and the crew! They were not only attentive to our needs, but they were very enthusiastic, and engaging and very responsive to out questions.
– tavodiaz
Policies
An option to reschedule or convert to a gift certificate is available up until 24 hours prior to departure. We are not able to offer refunds. Requests for cancellation, rescheduling or conversion to gift credit must be sent by email to [email protected]. Most activities run regardless of weather conditions. In the rare situation where the seller is forced to cancel the event, ticket-holders will be allowed to reschedule to another time (subject to availability), receive credit for a future event, or receive a refund.
Weather PolicyActivity may be canceled due to severe weather. The activity usually runs in light rain and other moderate weather conditions, but the seller may cancel the activity up to an hour before the start time in the event of severe or unsafe weather conditions. If the seller cancels the event, ticket-holders will be allowed to reschedule tickets (subject to availability), receive credit for a future event, or receive a refund.
Other PoliciesAll participants are required to have tickets for this event. According to the U.S. Coast Guard capacity rules, all passengers including infants and toddlers must have a ticket.
Parties of 12 or more will be contacted for an additional gratuity charge of 15%Classic Harbor Line will contact you directly within 48 hours of your purchase to take your credit card information for the additional charge. You must be reachable at the telephone number and email you provided.
