What to expect
- Enjoy a relaxing sail and picnic to the Boston Harbor Islands
- Take advantage of numerous photo ops as you discover the lush greenery of the islands
- Hear about sailing lore and historical background of the islands
- Get away from the city and enjoy what the Boston Harbor Islands have to offer
About this Activity
Note: A boxed lunch consisting of a sandwich, fruit, chips and dessert is served by the crew on this picnic sail (vegetarian options are included). Minors must be accompanied by an adult. Alcoholic drinks are not included in the price of the ticket, so please bring extra cash for the cash bar. Water and soda will be provided on board at no additional cost. Gratuity is not included in the price of your sail. Exact meeting location will be provided upon confirmation.
|Price||$76.00 per guest|
|Duration / Session||3 hours|
|Rating||26 positive reviews|
Morandah D.Sunset Harbor Cruise November 6, 2016
Lori B.City Lights Sail September 12, 2016
We had a beautiful evening! Great crew with lots of knowledge. Great way to see Boston and learn more about this historic city.
Jennifer Q.City Lights Cruise June 13, 2015
Service was great! We were running late and scared that we might not make it on time to board, they were nice enough to give us a service call to make sure we were on our way or needed assistance getting to them. I was surprised became most places don't bother in doing that, thank you once again
TJ .Sunset Sail September 30, 2014
Two buddies and I had a few hours to burn before meeting a group of friends out for dinner in the seaport area, so we decided to start our evening by going on a 2 hour cruise of the harbor. The crew was very friendly and helpful - they always made sure we had drinks in our hands (free waters/sodas, $5 wine/beer), and made sure we were comfortable, and having a good time. We took some great pictures of the city, had a lot of good laughs, and had an overall great time. Thanks - would definitely recommend!
Boat was very clean, easy for people to sit and walk around.
Emma .Sails & Ales July 7, 2014
This was a great cruise and a very relaxing day out. The staff were very friendly and the boat nice, clean and not too bumpy! The weather has been very hot in Boston, but we enjoyed the cool breeze and relaxing waters. Definitely recommended for your trip in Boston, its something different to all the other boat trips currently on offer!
Ying C.Day Sail October 16, 2013
If you're looking for the ideal relaxing afternoon sailing in a real schooner, this is it. Great crew, wonderful views of the harbor, and the eerie silence of the sails when the motor shuts off. Small passenger list makes for a relaxed vibe. Drinks are served at a reasonable cost, and a really friendly crew. Leaves from the central harbor area right by the aquarium.
Paul F.Sunset Sail September 19, 2013
Wow! Absolutely incredible and an absolute pleasure to be with Tim, Kerry, Will, and Brian. There was only 6 of us on the boat, and we had the run of it and it could not have been more perfect. It was a clear night, with a full moon, and a beautiful sunset. Once the motor was turned off and the sails took over it was absolutely incredible how peaceful Boston Harbor really was. This is an awesome date night, family outing, or even to enjoy solo and meet new people. I honestly cannot say enough and cannot wait to do it again!
Kel B.Sunset Sail September 15, 2013
We booked the sunset cruise for our daughter's 24th birthday and were not disappointed. The weather was perfect although they offer fleece blankets if you get cold. It is really wonderful in late August because you can go out in the daylight and return in the dark to the city lights. We all loved it. Crew and Captain were friendly and kind and fun.
Everyone should do this once. We are locals and this is so not touristy!
Lisa C.Sunset Sail September 1, 2013
My boyfriend took me on a sunset cruise for my birthday. The crew was very nice...the sail was delightful.....we had perfect weather....we were able to purchase wine/beer on the cruise as well as bring snacks which was nice.
I would highly recommend this cruise....
The only thing I would change was the length of the cruise as I would have been happy to spend more time sailing....it was that nice!
Balley B.City Lights Sail August 30, 2013
Great evening on board the Adirondack III for the City Lights Sail...this is a 90 minute sail around the harbor at night with all the lights of the city shining and reflecting on the water. We had a guest from Tennessee with us and this was a nice experience, seeing Boston from the water at night. Free water and soda, $5 wine and beer, and even blankets if you're chilly. Super clean and comfortable, attentive and knowledgeable crew. Fun watching the huge sails go up. Not much wind on our sail, but not much the crew can do about that! Still lovely.
Darla .Sunset Sail August 29, 2013
The Adirondack III sailing vessel is located behind the Boston Harbor Hotel. I noticed it while watching a concert this summer and decided to check it out one night after work. The crew was fantastic and the sunset and sail were awesome! Have tried sunset sails on other vessels in Boston Harbor - none of them compare. There was plenty of room for all, the Captain and his crew were extremely nice and very informative - it was a relaxing and great evening. It was not overcrowded, was clean and comfortable, and we actually "sailed" without the engine. I highly recommend!!
Lisa A.Sunset Sail August 22, 2013
A friend and I took the sunset cruise last night and it was amazing! Not only is the boat spectacular but the crew is super friendly and knowledgeable. Captain Tim is fun and very laid back and after a few safety tips he got us right out into the harbor-and quite smoothly I might add! It was amazing to watch the crew raise those huge sails over our heads and then see them fill with wind as we went along. The boat is very comfortable-we sat up front so we could get a better view of the city but from what I heard, there really isn't a bad seat on the boat.
Soda and water are free (where can you get THAT in Boston?!) and beer and wine is only $5. There weren't any snack on board but they said you could bring them with you if you wanted to. Next time, that's what I'll do. This would be an amazing date night but was also so much fun with my friend! I highly recommend you book a trip before the end of their season!
Kathy C.Day Sail August 18, 2013
My husband and I were looking for a multi-generational activity that would be fun for my older parents as well as my teen and tween. The 2-hour afternoon harbor cruise on the Adirondack III filled the bill. The views were amazing, the boat was beautiful and the staff was attentive and engaging. Overall it was a great vacation experience. I highly recommend this cruise.
Beverly M.Brunch Sail August 11, 2013
Loved our tour of the Boston Harbor! The crew was excellent....so polite and accommodating. Captain Tim was so friendly and the guys on deck..Will and Brad..were very sweet to everyone. I would recommend this boat to anyone wishing to spend a relaxing afternoon on the water.
Bonnie W.City Lights Sail August 11, 2013
Great staff, beautiful boat, knowledgeable crew... overall a great experience! We took the City Lights sail (9pm prompt to 10:30pm prompt, right on time) and it was wonderful. Complimentary sodas and water with beer and wine for only $5, with fabulous service I might add. Bring cash for drinks and tips. And a blanket for those chilly nights.
Highly recommended! We've already told all our friends and family how much we enjoyed the experience.
Barbara L.Day Sail August 8, 2013
Such a relaxing way to view the Boston Harbor Islands: from the deck of 80 foot Adirondack III Schooner. The 4 sails were up as we glided near many islands and Boston harbor attractions. We learned history and got a feel for how sailors previously depended on weather for travel. It was definitely a great 2 hour tour of the water on Thursday's 3:30 cruise. I enjoyed the freedom & flow of the adventure! This was a birthday gift to my 15 year old grandson (which I was thoroughly happy to experience it with him)!
Visited August 2013
Halley B.Sunset Sail July 23, 2013
The perfect way to spend a summer evening!
We took the sunset sail cruise last night and loved it! The crew couldn't have been nicer. Soda/water is free, wine/beer is just $5 (cash). You can bring snacks to enjoy during the cruise. The boat left the dock precisely at 6:30PM and returned at 8:30PM.
The boat is in great condition and very comfortable.
Two tips: bring cash (for wine/beer and tips) and warm clothing (although they have fleece blankets to use as well).
Sugar T.Brunch Sail July 22, 2013
Sailing on the Boston harbor with Classic was an excellent and relaxing way to spend an afternoon. The captain and crew were extremely friendly and knowledgeable. This tour will not necessarily give you the play-by-play of every building and site on the water, it is meant to be less formal and laid-back. If you are expecting a "tour guide" experience this is not it. If you want to get out on the water, enjoy the harbor, and relax, this is for you.
Bill G.Day Sail July 21, 2013
Best crew ever! Friendly, professional, just plain terrific! Ben and Alicia took great care of us and we really enjoyed the cruise thru the harbor. Highly recommend.
Chris L.Sunset Sail June 24, 2013
Took a sunset cruise on this boat this past Friday night after work and after an amazing 2 hours I know it certainly won't be my last. The captain and crew were laid back, fun and made the experience that much better. We happened to catch perfect weather and the views of the city from out in the harbor are perfect - the girlfriend and I could not stop taking pictures of the skyline as the sun started to set.
This is perfect for couples, friends, co-workers, whatever it may be. Give it a try one evening and you'll be thinking about your next trip before you hit the dock. We will definitely be taking more harbor cruises on the Adirondack III.
Laura S.Sunset Sail June 20, 2013
I didn't know what to expect heading out on this beautiful boat last night and I was totally WOWed. Believe it or not I had never taken a sail through the harbor and I'm a lifelong Bostonian. The crew was friendly, fun and made me feel 100% safe. The ship itself was beautiful! Wine, beer or other beverages were offered. We brought some snacks to nibble on and two hours flew by. This is something that I'll do over and over again. A perfect "outing" to do if you live here in Boston and want to do something other than go to dinner or the movies. Highly recommended. Located right behind the Boston Harbor Hotel at Rowes Wharf (through the arch).
Deanne F.Sunset Sail September 7, 2016
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Rahul G.Sunset Sail August 8, 2016
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Marco G.Sunset Sail July 22, 2015
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Jess F.City Lights Cruise July 11, 2015
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Robert A.Sunset Sail May 17, 2015
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