Boston 
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Boston Harbor Sail (Liberty Clipper)
Boston Harbor Sail (Liberty Star)
Sunset Sail (Liberty Clipper) 
Art of Mixology
Lunch in Little Italy Tour
Taste Gloucester Food Tour
The Dinner Detective
Suspect (Open Mic Comedy Show)
Woodstock Wednesday (Improv Show)
Sunset Sail
Licence to Carry and Gun Safety Course
Tai Chi (Newburyport 1) (Online)
Sail Boston Harbor at night and enjoy all facets of live entertainment on a tall ship! Actors dressed in period attire with play their fiddles or hornpipes as you sing and dance to sea shanties. You'll have a great time enjoying the entertainment and historic feel of the experience. The bar will be stocked with Madeira, Port, and the sailors favorite, the Dark 'n Stormy. This event will attract many singers and lovers of naval history and, of course, grog! Prepare for a rousing chorus of shanty singers and musicians of all sorts!
Note: You must be over 21 years old to attend this event. Cash bar available. There are limited seating, so if the boat is full, be prepared to stand.
Rum and Revelry Sail
What to expect
- Enjoy a sail out into the Boston Harbor with entertaining period actors and musicians
- Sit back and relax with your favorite drink supplied by a well-stocked bar
- Explore the naval history and prepare for a rousing chorus of shanty singers
- Partake in the drinking festivities with Madeira, Port, Grog and delicious beverages
This activity is completely sold out. Bucket List this activity to be the first to know about new available dates!
About this Activity
Key Highlights
| Price | $35.00 per guest |
| Duration / Session | 2 hours |
| # Sessions | 1 |
| Rating | 20 positive reviews |
Cancellation Policy
There are no refunds; all sales are final.
Reviews
(out of 20 votes)
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Jeff E.
Sunset Sail (Liberty Star) August 1, 2017A great time. We sailed on the smaller Liberty Star. The tour around Boston Harbor was narrated by Capt. Cody who explained the importance of sailing ships to the history of exploration, trade, and the progression of America. As we cruised along at a leisurely speed of 5 knots, Capt. Cody profoundly said "This is the speed that the world was discovered at." That's fantastic. Forget the motorized tours around the harbor. Go old school. Go sailing.
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Peter L.
Sunset Sail (Liberty Star) July 10, 2017Went on the 90 minute, Liberty Star cruise. It was a beautiful day and only about 20 or 25 guests on board. This is a real, old time style sailing ship that has actually sailed around the world twice. The Captain and crew were great as the set the sails and turned off the engine for a relaxing trip around boston harbor. Beer, water and "dark and stormies" were available for purchase. I highly recommend for visitor or life long Bostonians like me.
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Melina G.
Boston Harbor Sail (Liberty Clipper) July 2, 2017This was the perfect relaxing few hours of adventure. Great crew. Bar on boat! I would do it again in a heartbeat.
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Mark N.
Boston Harbor Sail (Liberty Clipper) June 26, 2017My family of three did the harbor cruise while on vacation. It's very relaxing to me out on the water, especially without the background noise of a motor or the smell of gas or diesel. The clipper ships are also extra cool in that regard. Beer and cocktails were cheap. In fact they didn't even charge us. I just gave the crew a big tip at the end. The views were spectacular and we just made it back before some weather rolled in. If you like boat rides, this one will not disappoint.
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Tom K.
Boston Harbor Sail (Liberty Clipper) May 7, 2017the Liberty Clipper sailed out of Nassau for a 6 night 7 day cruise. The boat was built in the early 80's but was a great and authentic reproduction of a 1920's boat. there was a crew of 9 and paying guest were 13. We got to know and interact with Capitan, crew and guests very quickly. pack light the cabins and heads were very small but no worries you will be top side or on a virtually uninhabited beach any way. beverages were self serve however all crew members would serve any reasonable request any time. Our mix of passengers was from about age mid 20's to early 80's. All were great people to hang out with. most were mid 70's. The boat had quirks but for me that made it better. this is not the typical cruise boat experience.
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Jennifer K.
Sunset Sail (Liberty Star) April 9, 2017Last week was our third time vacationing on Liberty's tall ships. Our first 2 were on the "Clipper" in the Bahamas. Last week was on the "Star" in the US Virgin islands and the British V Is. All 3 were amazing. The crew was outstanding! We learned so much and experienced wonderful places to visit and great food! These are older wooden boats so don't expect 5 star accommodations. But if you want to let your hair down, stay in your swim suit for a week, love the water and just want to have fun! This is it! The Liberty "Star" only accommodates 6 passengers and we are all friends. We had a terrific time! We most likely will do it again! FYI this is for adults. I highly recommend it! Fabulous vacations!
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Judith V.
Boston Harbor Sail (Liberty Clipper) April 6, 2017Called to book a dinner cruise, didn't have my dates available but recommend me some competitors very nice since this will be our first time in Boston!! Loved his attitude and god willing if we go again we will for sure take a cruise with them!! Thank you sooo much.
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Ana M.
Boston Harbor Sail (Liberty Clipper) October 18, 2016I was just thinking about my experience on the Liberty Clipper last month... I was having dinner with my family at the Chart House when we saw the Liberty Clipper sail into the harbor. It was such a beautiful boat! I called the phone number listed on the side for more information. The staff was very friendly and walked me through the reservation process for a sunset cruise that evening. When we got onto the boat it was a little overwhelming at first, especially for the kids. However, all of our apprehensions were put to rest when the captain put us to work raising the sails (wow, those things were heavy!). The crew was great, the Dank n' Stormies were strong, and the skyline view was breathtaking.
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Gerry F.
Sunset Sail (Liberty Star) September 12, 2016We sailed with Liberty Fleet twice this summer, and were very impressed. This is real sailing. Current technology can be engaged when necessary, but this is essentially the way it was done in years past. The captain and crew, in addition to sailing the ship, work hard to keep the customers happy and entertained.
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Jack S.
Sunset Sail (Liberty Star) September 3, 2016I wish I could give them more stars. This was one of the best spur of the moment things I've ever done the crew was amazing fraedo pours a perfect dark and stormy the captain was knowledgeable and funny. I can't wait to book a tour with them for the virgin islands. Do your self a favor take there tour.
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Lindsey N.
Boston Harbor Sail (Liberty Clipper) August 8, 2016My friend and I did an overnight stay a few days ago. It's a hostel-type setup so you will be rather roughing it. My friend and I were worried about the small room at first but we never spent any time in it really so we didn't mind. The real experience happened above-deck. At night everyone hangs out up there and we had a blast. Everyone was super nice and welcoming, and totally accommodating. Dennis was a delight and Johnathan a riot. We met some awesome people there and most of our positive memories from the trip will be from that first night on the Clipper. We intended to do a 10:00am cruise with them the next day but our plans for the trip and my feeling ill didn't allow us to, which was a bummer. Would totally come back!
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Kevin D.
Boston Harbor Sail (Liberty Clipper) September 20, 2015September 2015 - I was traveling solo and this was my first experience in Boston and am so happy I was able to book a cabin on the conveniently located Liberty Clipper. Cabins may be small in some peoples' opinion, but they are certainly comfortable aboard this 19th century replica. The crew was relaxed, kind, and fun to be around. The ship is very clean and you are made to feel right at home. Overall, if you are willing to sacrifice a few small luxuries like size of rooms/bathrooms and being able to return to your cabin while the ships are on their sailing tours, I would highly recommended this for your lodging. Also, if you're like me and cherish unique experiences rich with history and perspective, you'll love it. The booking comes with a discount on the sails they take throughout the day, as well! That was also great.
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Tim P.
Boston Harbor Sail (Liberty Clipper) September 7, 2015My wife and two friends of ours took a sunset cruise from Boston Harbor on Saturday, September 5th and then proceeded to spend the night on the Liberty Star, the smaller of the two ships in Boston. Captain Gil provided a very relaxing sunset cruise on the harbor. But it was the hard working crew of Ben, Griffin, and Justin that saw to our every need that night. They made us very extremely welcome and were totally there for us from start to finish. I hope they come back next year so that we can sail with this fine crew again. It was amazing!
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Cameron C.
Sunset Sail (Liberty Star) June 15, 2015Great Service! I will definitely be using the site again!!
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Pablo C.
Boston Tea Party Sail August 15, 2014great family experience, specially if you have never been in a big sail boat. Arrive early and take your camera. If you get sea sick, it may not be for you...
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Christine T.
Boston Harbor Sail (Liberty Star) August 2, 2014Good ship, good crew. obnoxious bunch of tourists on the boat. But a nice sailboat ride. A bit pricey considering the Boston Harbor isn't THAT picturesque, but worth a trip here and there if you've never been on a sail boat.
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Lindsay D.
Boston Harbor Sail (Liberty Star) August 1, 2014We set sail on the Liberty Star for a work outing including 27 people last week and had a great time! The boat was clean and the crew members were very nice and informative. We had the boat to ourselves and were able to bring our own food on board. We had a perfect night for a sail and got to relax with drinks and a beautiful view of the harbor.
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F G.
Sunset Sail (Liberty Star) July 29, 2014The crew is very friendly and fun. We got to help hoist the sails before relaxing with our drinks. What a great time! The view of Boston from the water is magnificent!
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Seth G.
Boston Harbor Sail (Liberty Clipper) June 16, 2013It liked helped that it was sunny and winding for the two hour tour are the harbor. It was a good time and was worth the cost. The crew were friendly and answered your questions. Being on the sail boat, everyone was on deck, which was real nice. If you are on the water and the weather is nice, you should not be in the cabin. It was also very nice that they had a bar on deck and the drinks were flowing.
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Carlos G.
Sunset Sail (Liberty Star) September 19, 2015Did not leave comment
