We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.
Sponsored by:
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Sponsored by:
Get directions
Address: 211 E Main St, Gloucester, MA 01930-4161
Phone Number:
+1 978-948-5434
Website
Description:

Windfall, our elegant 49-foot sailing vessel, is available for day or...

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.We head south in autumn to go sailing in the beautiful, sunny Sea of Abaco from late February through May. Meet us at our base of operations at the fabulous Baker's Bay Club in Great Guana Cay, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas.

read more

TripAdvisor Reviewer Highlights

Read all 81 reviews
Visitor rating
  • 80
    Excellent
  • 0
    Very good
  • 0
    Average
  • 1
    Poor
  • 0
    Terrible
Absolutely Fabulous Day Sailing

Capt. Raffi and Lisa are down to earth wonderful hosts, couldn't ask for a nicer crew to spend the day. Every step of the way they were gracious and accommodating. We would sail... read more

5 of 5 bubblesReviewed 1 week ago
Harvey776245
,
Marietta, Pennsylvania

Similar Things to Do in Gloucester

Add Photo Write a Review

81 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
Showing 81: English reviews
Marietta, Pennsylvania
1 review
5 of 5 bubbles Reviewed 1 week ago

Capt. Raffi and Lisa are down to earth wonderful hosts, couldn't ask for a nicer crew to spend the day. Every step of the way they were gracious and accommodating. We would sail with them any day!!! Windfall is a Beautiful Boat ,almost as nice as the crew !

Helpful?
Thank Harvey776245
Newburyport, United States
2 reviews
5 of 5 bubbles Reviewed October 11, 2016

We had the enjoyment of sailing with Captains Raffi and Lisa in the Bahamas two years ago - a wonderful experience. When our relatives from the West Coast were visiting, we decided a sail with Raffi and Lisa in Gloucester would be a nice adventure for them. It was better than nice - it was truly delightful. We were blessed... More 

Helpful?
Thank Judy F
Portland, Oregon
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed October 6, 2016

The day trip around Gloucester harbor and bay was the best ever. Captains Raffi and Lisa were very gracious hosts and the Windfall is a beautiful yacht. Great company, great stories about the harbor and other sailing adventures. Highly recommended for either a day trip or longer sailing adventure.

Helpful?
Thank kcf929
1 review
5 of 5 bubbles Reviewed September 16, 2016

I'm a photographer and chartered with Lisa and Raffi for a photoshoot. They went out of their way to make everything go smoothly and provide me an opportunity to get some fantastic images. The boat is gorgeous!

Helpful?
Thank Erik P
Lynn, Massachusetts
1 review
5 of 5 bubbles Reviewed September 11, 2016

We sailed with a group of 11. Captains Raffi and Lisa were awesome during our wedding sail. The Windfall was beautiful, absolutely loved this sailboat. It's much more impressive in person than in photos. Lisa was extremely accommodating serving our guests, making sure everything was perfect and taking photos. Our guests loved the entire experience. We would love to charter... More 

Helpful?
Thank kmitchell70
Novato
Level Contributor
11 reviews
common_n_attraction_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed September 5, 2016 via mobile

Capt. Raffi and his 1st mate Lisa made our group feel special. They are very experienced sailors who's sailboat is in excellent shape. We hired on for a 3 hr sail which seemed to go by quickly. Very relaxing. Highly recommend.

Helpful?
Thank kwkirbo
Level Contributor
5 reviews
3 attraction reviews
5 of 5 bubbles Reviewed September 2, 2016 via mobile

There were 3 couples traveling in our Rv's on a 3 month trek from California to the Candian Maritimes and New England coast. We all jumped on the chance to have a private sailing experience out of Gloucester. As others have said, Lisa and Raffi are lovely people and made us feel welcome; like old friends. Highly recommend this adventure.

Helpful?
Thank WaltandJackie J
Gloucester, Massachusetts
Level Contributor
6 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed August 22, 2016

Celebrated my father in laws birthday with a fantastic sail aboard "Windfall" - What started as good idea a few years ago - has turned into an great annual event... which the entire family looks forward to. (we even had one of my teenage daughters leave a friends early to drive 1.5 hours back to Gloucester to make sure she... More 

Helpful?
Thank James B
Boston, MA
Level Contributor
98 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 56 helpful votes
5 of 5 bubbles Reviewed August 9, 2016

We loved our day sail aboard the Windfall, a sleek 49-foot Hinckley Luxury Yacht - absolutely stunning. Captain Raffi and First Mate Lisa took our party of 8 adults along the Gloucester shoreline for an unforgettable experience. We had perfect sailing weather and our time at sea was more fun than we could possibly imagine. You get a different perspective... More 

Helpful?
Thank KenBoston_MA
Manchester, NH
Level Contributor
6 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed August 8, 2016

We took a family cruise with Capt Raffi and Lisa aboard the Windfall. This is a beautifully restored Hinkley 49 sailboat, with 3 sails and 2 cockpits. We had a 5 hour cruise around the Cape Ann shoreline. Capt Raffi and Lisa are very knowledgeable about the area and the history. Lisa pointed out Hammond's Castle, various light houses and... More 

Helpful?
1 Thank FlyingDC

Travelers who viewed Defiance Sail Charters - Day Tours also viewed

Gloucester, Cape Ann
Gloucester, Cape Ann
 
Gloucester, Cape Ann
 

Been to Defiance Sail Charters - Day Tours? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Defiance Sail Charters - Day Tours and other visitors
1 question
Ask a question
Boston, Massachusetts

See all questions (1)

Questions? Get answers from Defiance Sail Charters - Day Tours staff and past visitors.
Posting guidelines
Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?