What to expect
- Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
- Ask your knowledgeable staff and crew anything you'd like to know about the sights
- Experience the joy of a leisurely sailing cruise
- Enjoy the ride, see the sights and have a drink onboard
About this Activity
Note: No food is included; feel free to bring your own picnic. Complimentary Beer, Wine, Champagne, and Soft Drinks.
|Price||$45.00 per guest|
|Duration / Session||2 hours|
|Rating||44 positive reviews|
Kristen T.Sunset Harbor Cruise July 24, 2017
I took my girlfriend on a sunset sail for her birthday and we both loved it. The crew was excellent! Very accommodating, helpful and had great personalities. We were on the Adirondack III, which is a beautiful boat. It was very clean and a smooth ride. I would definitely do this again!
Don E.City Lights Cruise July 18, 2017
My wife and I just sailed on the Adirondack III out of Boston Wharf. A fantastic day, nice breeze, clear sky, warm not hot and a beautiful 80 ft sailboat. This was a gift. We are not sailors and put this off for three years, because my wife gets sea sick, and we kayak inland on nice days. Finally the stars aligned and we booked our 2 hrs going out at 3:30 pm as the sun was a little less intense. The guys on the boat were fantastic, telling stories and answering questions. They are seasoned sailors and the trip was so much fun. If you love the water, you must do this. If you are not great on the water, Bonine (over Dramamine) is great and wont knock you out. Do it-just do it !
Linda M.Sunset Sail July 5, 2017
We were on the Adirondack III which is a gorgeous schooner. I do think the boat you choose makes a big difference. The boat was lovely, clean and was not too crowded. Only a handful of people fit on the small benches so we sat on the center deck part (nautical terms are obviously not my expertise!). Bring your own snacks and the super efficient staff will sell and serve you beer and wine and soft drinks.
The views are tremendous and if you're lucky enough to have the perfect weather it will be a slice of heaven you'll want to repeat.
Staff was organized, efficient and friendly.
Sharon K.Sunset Harbor Cruise July 2, 2017
Wonderful evening cruise! Once the sails went up it was truly heaven. If you want to drink they have that or free water and pop. If you get cold they have blankets. The crew was very attentive and the captain totally informative. Only here in Boston for a week, but would do this sail adventure again. Well worth the price!
Dave H.Sunset Sail June 16, 2017
Great boat, and an excellent way to spend 2 hours. Crew is very attentive and service is great. If you haven't been on the Harbor, one of their trips is a nice way to get out on the water. I've done the mid afternoon cruise and the sunset cruise. Both are great. Bring a fleece in June. Gets chilly towards the end of the day.
J D.Sunset Harbor Cruise May 29, 2017
We took a sunset cruise and it was a little on the cool side for memorial day weekend it was still a great time. The crew was friendly and personable. They were interacting with everyone onboard all throughout the cruise. The cruise was on time both leaving and returning to the dock. It was a nice slow sail allowing you to see the various islands and also get a look at planes taking off and landing if you want to. We saw a really nice sunset on the way back to dock which made for some great pictures. I'd definitely go with them again for a cruise.
John K.City Lights Cruise May 28, 2017
Always nice to be on the harbor. Nothing like being on the water. Cruises at night show the beauty of city lights. Fresh air and the beauty of the harbor islands. Boat crew is amazing and friendly. One of the most enjoyable experiences when visiting Boston is seeing it from the water. U appreciate the incredible city it is.
Morandah D.Sunset Harbor Cruise November 6, 2016
Jane F.Sunset Sail October 16, 2016
Wonderful evening on the sunset cruise! Lovely narration as well ! Great way to start our night in Boston! Well highly recommend to all our friends !
Gerry F.Sunset Harbor Cruise September 19, 2016
My wife and I, Boston cruise junkies, had on one of our best experiences ever on Classic's Harbor Islands cruise. The ship was beautiful and very comfortable. The staff was extraordinarily attentive. The tour of the islands was as complete and informative as I've ever experienced.
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.
Patricia H.Sunset Sail August 14, 2016
This is a very enjoyable and informative cruise with beautiful scenes of Boston and the islands. Highly recommend for both tourists and locals. The crew and staff are great. This was our second cruise as we really loved it.
Richard D.City Lights Cruise August 13, 2016
The crew were very professional and fun. They interacted with the passengers and made a great evening on the sunset sail (Adirondack 3). The skipper was very knowledgeable and provided interesting facts. We would certainly do this again, serenity on water!
Glo R.Sunset Harbor Cruise August 1, 2016
Great experience on the northern lights. The city lights cruise was awesome. Loved the charm of the ship and the great service provided by the crew. It is the perfect setting for a romantic evening with your other half. We had an amazing time and would highly recommend it.
Thomas W.City Lights Cruise July 26, 2016
An excellent experience. I went on their 2 hour cruise in July during a visit to the Boston area. 100% will be going back to them in future visits for some more boat excursions. Crew was fun and knowledgeable, boat was beautiful, and the people I met on the trip were wonderful.
Barbara B.City Lights Cruise July 20, 2016
My cousin and I had a wonderful evening on the Northern Lights cruise. The staff was delightful! Very informative and accommodating. The boat was impeccably clean. Will be cruising with them again, I am sure.
Happy P.City Lights Cruise June 26, 2016
A great day out guys!! Nothing like a beautiful afternoon out on a gorgeous Schooner!! It's a small group outing- not like the huge boats! You get to hear a little history, and really enjoy the harbor!! The Captain and crew were delightful and took the time to chat with all the passengers- and their love of sailing was apparent- they weren't just doing a job. This is a great experience if you want to see the city from the harbor.
Rebecca L.Sunset Sail May 13, 2016
Decided to book a sailing with the Adirondack III as a way to celebrate the beautiful weather we were having. My friend and I had a fantastic time. The crew was friendly and knowledgable. The ship was beautiful and comfortable and the views phenomenal. They had a selection of beer and wine for purchase on the sail, or sodas and water. We were on the second sailing of the year, still a bit early in the season so it was a little cold- but the crew had warm blankets for us and it ended up being perfect. It was a really relaxing way to spend the afternoon and I would absolutely recommend this experience to my friends.
Kathy J.Sunset Sail August 1, 2015
We took a Day Sail yesterday because we had a few hours between a conference ending and our flight back home. Our crew was friendly and accommodating with questions from the onset. It was clear that they enjoy what they do and are about providing the best customer service possible. A perfect sunny and breezy afternoon rounded out a perfect sail.
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
Erin B.Sunset Harbor Cruise December 7, 2014
What a unique and enriching experience! My boyfriend surprised me with a three-hour sail through Boston Harbor for my birthday. The sail included lunch and an informative guide (the captain) who talked about the history of the Harbor Islands, lighthouses, etc. There were also two staff on the boat who answered questions, served the food and offered beer and wine for purchase. It was a fantastic time!
It was a bit chilly on the water in October, but we wore our winter coats and were fine. The way out was colder because we were on the shade-side, but on the way back we were pretty warm from the sun (not to mention the beer, wine and hot apple cider!)
Extras: There are two bathrooms on the boat, blankets for when it gets cold and you can walk around to get different views of the skyline, harbor, boat, etc
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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