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 626 reviews
Sort by: Most recent
Susan_D, Aug 2026
This is so relaxing and well done. You can get beverages on board and crew is very knowledgeable. Highly recommend!!
Ns_C, Aug 2026
We went on a so-so weather day, so it wasn't crowded at all. The tour was lots of fun, and the crew was very helpful and personable. I would have liked to have a few announcements about what we were seeing, but if you ask the crew, they would tell you.
Emily_R, Aug 2026
Cannot recommend this experience enough! The boat and views were beautiful, but the crew was what really made the experience great! Michael, Charlie, and John were so helpful and friendly, and made the experience so much fun! Thank you for the great afternoon!
Crystal_B, Aug 2026
This whole vibe was just Oolala. You just get on the boat and feel the breeze and look at the skylines all around you. Don’t over think it, just go on the boat ride.
Soren_J, Aug 2026
Captain & crew are excellent sailors with such knowledge of Boston Harbor’s history that you could call them the Sailing Docents of Boston Harbor. Remarkably, the Adirondack II is the exact same two-masted schooner my wife and I enjoyed as guests about 11 years ago in Newport.
Dean_L, Aug 2026
The crew was very helpful and knowledgeable. They do sell beverages on the ship but you are able to bring your own onto the ship too.
Julia_L, Aug 2026
It was great being on the water and seeing Boston Harbor in a unique way. The Captain and crew were very informative and personable.
Philip_R, Aug 2026
Beautiful serene couple of hours boating in the Harbor on a beautiful boat, the Adirondack II. Captain Eric and crew were great.!! Highly recommend.
Jennifer_O, Aug 2026
Great cruise! Very chill and relaxing. Crew was super friendly. Highly recommend. Suitable for all ages.
Lukasz_S, Aug 2026
Wonderful time spent sailing, totally relaxing and totally fun. One of the best things we did in Boston.
Karl_G, Aug 2026
Great day! Great way to see the harbor. No doubt the best crew out there...Charlie, Eric and Big Dawg!!
Andrea_W, Aug 2026
It was a fun and relaxing tour of the harbor. The crew was engaging and the whole experience was fun.
Becca_H, Aug 2026
Captain and crew are so knowledgeable & fun to talk to on the tour! You will learn so much about Boston, the harbor, and sailing. Just ask! The views are amazing & seeing the harbor islands from a tall ship is such a fun experience. We loved being able to feel the ocean as we sailed.
Sandy_S, Aug 2026
The boat ride is so relaxing. We loved the oysters and adult beverages that were served. The crew was attentive but chill. We would absolutely do this again.
Sean_G, Jul 2026
Wonderful experience, great for families. The crew was outstanding, funny, and if you have a young child they may even be able to captain the boat!
Tanya_B, Jul 2026
We absolutely loved this sailing trip and would do it again! Our weather was perfect which absolutley helped! Terez was our captain and did great. Alex and Charlie were great and had lots of great information about the area and history. It was our first trip on a sail boat and very memorable.
James_W, Jul 2026
Great job, friendly staff, great captain. E has a bottle of champagne and enjoyed the water and the sun. The staff was super friendly and recommended a great lunch spot.
Stephanie_V, Jul 2026
I had a terrible migraine- but the sail was still so relaxing and wonderful. My mother has never been to Boston, or even on a sailboat so the fact that she was impressed and had a good time was the high point for me.
We came from Texas so, being out in the sun in late July is not something we get to enjoy regularly lol - 2 very enthusiastic thumbs up 10/10 would recommend
Eileen_G, Jul 2026
We had a fantastic time on this Boston Harbor Sail Tour. The crew was very enthusiastic and knowledgeable about the Boston area. We highly recommend this tour!
Jim_R, Jul 2026
While the weather wasn't the best, very cloudy, windy and wet and limited where we could go, we had a good time chatting with the crew, who were very knowledgeable about the area, and we meet some fun new people!
Ann_L, Jul 2026
We had a wonderful day filled with sun and breeze! The captain and crew were wonderful and going around the harbor was relaxing and romantic.
Logan_B, Jul 2026
Excellent experience and service. Would sail again. Crew was knowledgeable and friendly. A++++++++++
Kasey_H, Jul 2026
My family and I had a great time! They were visiting from Florida, first time on a sail boat and the crew was very kind, informative, and all around amazing. We will definitely be back!
Alissa_B, Jul 2026
Sail boats lean, if you don't like the boat tipping go on a catamaran or a motor yacht.
This sail on Adirondack II was awesome! Great captain and crew, saw a lot of Boston Harbor. I would definitely sail with them again!
Adelete_B, Jul 2026
We had a great time the crew and the captain were great. I will definitely do it again. We love boston
Judith_S, Jul 2026
They will be allowed to steer the ship if they want. It was the highlight of my trip to Boston. I got a great recommendation for a place to try clam chowder and it was very good.
mma2450carole, Jul 2026
Wonderful sail around the Boston Harbor. Oysters shucked in front of you and good selection of beverages. Crew were delightful and knowledgeable about the area. First time on a sailboat for us and truly enjoyed the experience.
James_S, Jul 2026
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.
Beth_C, Jun 2026
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!
Luis_S, Jun 2026
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.
Response from Host, Jun 2026
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
From $54.44
per personup to 24 hours before the experience starts (local time)
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