United States
Massachusetts (MA)
Cape Ann
Gloucester
Things to Do in Gloucester
Defiance Sail Charters
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Defiance Sail Charters

See all things to do
See all things to do
Defiance Sail Charters
5
153 reviews
#3 of 45 Outdoor Activities in Gloucester
Boat Tours • Water Sports • Day Trips
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12:00 AM - 11:59 PM
Monday
12:00 AM - 11:59 PM
Tuesday
12:00 AM - 11:59 PM
Wednesday
12:00 AM - 11:59 PM
Thursday
12:00 AM - 11:59 PM
Friday
12:00 AM - 11:59 PM
Saturday
12:00 AM - 11:59 PM
Sunday
12:00 AM - 11:59 PM
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About
Windfall, our elegant 49-foot sailing vessel, is available for day or overnight sailing charters.We dock for the summer season (June–October) in historic Gloucester, MA, in Smith's Cove, within walking distance to the famed artist colony of Rocky Neck. Summer charters are also available out of Boston or any accessible New England port. Or, use Windfall as your floating B&B (Boat & Breakfast dockside) while visiting the lovely Cape Ann region. In autumn we head south to go sailing in the beautiful, sunny Bahamas from late February through May. Meet us at our base of operation, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas. We practice all state and local covid-19 sanitation guidelines.
Gloucester, Massachusetts
Awards
Travelers' Choice
2023
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(22 reviews)
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
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5.0
153 reviews
Excellent
151
Very good
1
Average
0
Poor
1
Terrible
0
Jeff B
Needham, IN16 contributions
The Perfect Afternoon Sail
Aug 2020
We joined Captain's Lisa and Raffi for a 3 hour afternoon sail, and had a fantastic experience. The boat comfortably accommodated the 9 of us along with the additional cooler we brought for our lunch (they served drinks, nut mix and a veggie platter). Sailed for around 2.5 hours and then dropped anchor and jumped into the 72 degree ocean ! In addition to the perfect conditions, both Lisa and Raffi were very personable and shared stories about their adventures and the Gloucester area, and also let us navigate for part of the trip. Also took quite a few photos both on the boat and in the water. Prior to booking, I read most of the reviews, and felt that we would be making a good and safe choice, it turned out to be a perfect choice. If you have the opportunity, spend a few hours on Windfall while they are in port
Written August 6, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
lucyallsn
Cleveland, Ohio56 contributions
Awesome family day in Gloucester!
Aug 2021 • Family
We had a great day with the four adults and 4 kids (7-13)
on the boat with Raffi & Lisa! Raffi was awesome with the kids - super friendly and kept them busy telling them about the history of Gloucester and the surrounding areas, snacks and juice boxes, knot tying and helping with the sails. he also had a great visitor book they could color a photo to remember their day. it was a nice big bit with bathroom perfect for the size of our party. they were very accommodating even moving up our sail time last minute to account for incoming weather. We’ve been visiting Gloucester for 40 years and this was a first for us! Highly recommend!
Written August 7, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
AEspo
1 contribution
Picture Perfect Wedding
Jul 2020
We decided to elope aboard "Windfall" out of Gloucester Harbor and are so incredibly happy with our decision. From the very first correspondence with Captain Raffi and Lisa, we knew we were in good hands. The ship was impeccably clean and all Covid necessary precautions were taken to keep us safe. We had perfect weather and enjoyed a sail out past the harbor and even saw a whale! We were married at sunset with Captain Raffi performing a beautiful, intimate ceremony. Lisa captured every moment and sent us photos that night so we could share with our family and friends right away. Their thoughtful surprises and hospitality really made our night special. I don't leave reviews often but Captain Raffi and Lisa went above and beyond to make our wedding great. There was not a single thing I would change about our wedding day. Thank you so much Captain Raffi and Lisa for being so responsive from start to finish and making our wedding day completely stress free and more perfect than we ever could've imagined. We can't wait to sail with you again! Allison and Paul
Written July 29, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Christine B
Groton, MA1 contribution
Most amazing day!
Jul 2023 • Family
Great day at sea with my daughter and two grand-daughters aged 7 and 4. Lisa and Raffi are welcoming hosts and skilled sailors. The grandkids had never sailed before but soon Captain Raffi had them hoisting sails, steering the boat, driving the dingy and just generally falling in love with sailing! The boat is beautiful and very comfortable. Would def recommend for families, couples and anyone who wants to experience sailing at its best.
Written July 31, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Wander79544
Rockport, MA7 contributions
Beautiful sail off Gloucester
Aug 2021
I just took my wife out on the Windfall for her birthday. The day far exceeded our expectations of a wonderful sail. The boat is a classic, very beautiful, seemingly easy to handle (they let us steer!), and comfortable. Capt. Raffi and His first mate, Lisa, are two very nice and very competent people. The sailing was beautiful and impressive and fun and we were treated like royalty; they even supplied a birthday cake and we had a little party. We cannot say enough good and nice things about this trip. If you want to sail on a wonderful yacht out of Gloucester, you cannot go wrong with this...really!
Written August 8, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
160sedram
Bedford, NH6 contributions
AWESOME
Aug 2022
This is my fourth time sailing with Lisa and Captain Raffi. Each time is perfect and interesting. It is a wonderful three hours spent on the water laughing, enjoying the water and just relaxing. Believe it or not, the internet works great on the boat. This makes for a great celebration or just for a fun time out. Lisa and Captain Raffi are such wonderful hosts and cannot do enough to make your time with them perfect.

For the quality of the boat, the extras such as wine/beer/snacks and pictures at the end, this is quite reasonable for what you get. They book quickly so I wouldn't hesitate to book with them as soon as you know your date.

You might even get lucky and see "Wicked Tuna" being filmed as we did on one of the
Written August 15, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
JoyJoy
1 contribution
Great memories
Sep 2020 • Solo
I don’t know where to begin Captain Raffi and Captain Lisa are two of the most beautiful souls you can meet. The day my boyfriend and I decided to charter this beautiful sailboat the Windfall Captain Raffi made sure we were accommodated in every way. The history the both captains gave of Gloucester had the two of us on the edge of our seats. From the attentiveness of Captain Lisa to the charming warmness of Captain Raffi we couldn’t have had a better more relaxing experience. When we stepped onto the Windfall they were delightful acquaintances and when we stepped off they had become life long friends. If you want to charter a beautiful breathtaking vessel to make memories that will last a lifetime, PLEASE charter the Windfall with Captain Raffi and Captain Lisa because the best thing about memories is making them!
Written September 9, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Climber37870678941
2 contributions
Gloucester Harbor Sail
Jul 2023 • Family
We had a wonderful experience with Raffi and Lisa! We explored around Gloucester and all of the beautiful sailing communities in and around the harbor. The weather wasn't completely cooperative but we were having so much fun, we hardly noticed! Lisa's food was fantastic and Raffi's tales of being on the water were engaging and exciting. We all left the boat wanting to give up our day jobs for a life on sea!
Written July 11, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Jeffrey C
2 contributions
Last Minute-Great Experience”
Jul 2020 • Couples
Raffi &Lisa are not only experienced captains but gracious hosts as well . From the moment you meet them you feel comfortable and know you are in for a picture perfect sail. They share a wealth of knowledge of Gloucester History and show a genuine interest in your stories as well. Experienced or not you are invited to get behind the wheel of this magnificent yacht and navigate you’re sail!. I should mention that I booked the sail last minute due to an engine issue on another yacht and Raffi and Lisa “saved the day”!. You made our summer and we will be back . If anyone reading this is looking for a great day outing or even overnight excursion, this is the experience you’ve been looking for . Thanks Captain Raffi and Lisa.
Written August 2, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Stephanie G.
Somerville, MA1 contribution
Sailing
Sep 2020
We had so much fun sailing through Gloucester Harbor and then out into the open water. We were two families with 3-year old who were THRILLED to be on a boat, seeing the other boats go by, the birds, and the castles on the shore. Lisa and Raffi were great with the kids, gave us delicious food and told us all about the things we were seeing in the harbor, and about sailboats. They have a lot of experience sailing and it was very cool to hear their stories. We were lucky to have a gorgeous day, clear skies, we could see all the way to Boston at the horizon. Highly recommend.
Written September 19, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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