Sightseeing Day Sail around Boston Harbor
Description
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.
Tour Options
Itinerary
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
Sail by Fan Pier and see the spanning Moakley Federal Courthouse, the World Trade Center and Harpoon Brewery.
Sail amongst the Inner Harbor Islands of Boston Harbor including Castle Island featuring Fort Independence and the Donald McKay Monument, Spectacle Island, and Long Island with the Long Island Head Light House.
Highlights
What's included
Traveller Ratings
Important Information
- 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
Reviews(576)
This is such a wonderful cruise and experience. We make sure to book every year. The crew are amazing; very kind, knowledgeable and friendly. Claire was especially wonderful. We highly recommend to anyone who loves a day sail.
Eric and the crew did a great job of making us feel at home. They even let my 11 year old take the steering wheel as we navigated the Harbor. The cool breeze was a great break on a 90+ degree day. Thanks for such a great time.
A beautiful way to see the city from another point of view! We were on the adirondakII with Capt Michael, Mike and Keira. They did a fabulous job!
Boring. Just zig zags in front of city. Guides do not explain anything only offer drinks and expect tip afterwards. They should give some history presentation or talk about the architecture. Seats are hard and uncomfortable.
Luis, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are sorry to hear that this experience was not as lively or as entertaining as you had hoped. The excitement and speed of the sailing portion can vary from slow and relaxing to thrilling, but unfortunately we don't have much control over that aspect. The route can also vary significantly depending on the wind of the day. We appreciate your thoughts about adding narration and do encourage our guests to ask the crew all about the area if they want. We hope you will get the chance to join us for a more exciting sail in more favorable conditions. - Classic Harbor Line Boston
Lovely evening on board with lovely staff. What’s not to like.
Scott, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear you had a lovely evening on board and that our friendly crew made such a positive impression. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston
A few days prior to this sailing adventure, we had been sailing with a different group. On this trip, there were two groups of people who got drunk (which was fine) and were yelling over the noise of other people and the wind (this was not enjoyable). On the other sailing, the captain and mates educated us about the areas we were sailing near. This trip did not because it was so loud we wouldn't have heard them anyway. Some of the drunk people also left their trash and it blew onto me, getting my shorts wet. This trip was such a disappointment.
Holly, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are sorry to hear that this experience was negatively affected by the noise and debris from the other groups. We will let our crews know to keep a closer eye on these aspects and to step in if they can help in these situations. We hope to be able to provide you with a better experience on another occasion. - Classic Harbor Line Boston
An absolute fantastic trip. The crew were amazing, patient, even with a small child running up and down the deck without parental supervision. The child climbed onto the side where there were only ropes preventing him from going overboard! Again, no parents watching over them. We decided last-minute to get tickets and we are so glad we did. Changing gusts of winds from nothing to full sails, it was all handled extremely well. I will definitely be returning!
Great trip. Just long enough to get a sense of the harbour. The captain and two crew were very knowledgeable and it was a lovely, relaxing way to spend a couple of hours.
Annabelle, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are delighted to hear you enjoyed your time on the harbor and found the experience relaxing. It is wonderful to know the captain and crew were knowledgeable and made the trip worthwhile. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston
It was an incredible experience and our grandson left with a goal to learn how to sail. No higher praise than that!
Patty, thank you for booking a cruise with us and taking some time to provide your valuable feedback and recommendation. We are ecstatic to hear that your grandson had such a memorable time and was well taken care of by the crew. It means a great deal to know our friendly crew left such a lasting impression. Inspiring a new generation of sailors — there truly is no higher praise! We hope to see you again soon! - Classic Harbor Line Boston
Went with me and my two children (20 and 10). A lot of fun. Fun trip and beautiful traveling. Crew was extremely friendly.
