Windward Islands Yachting & Travel Reviews 236

TrustScore 5 out of 5

4.9

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Rated 5 out of 5 stars

We booked our catamaran vacation through Barry and everything was extremely seamless. We were bringing our young kids along and one person in our party has sever food allergies and Barry was really he... See more

Rated 5 out of 5 stars

Barry was absolutely amazing and played such a huge role in making two of our favorite trips ever, one to the Bahamas and one to Tahiti both during NEWYEARS. From start to finish, everything was incre... See more

Company replied

Rated 5 out of 5 stars

Barry at Windward Islands Y&C was our POC for organizing a fantastic charter experience in Auckland. He found a boat when nobody else could, and moreover the company he found was run by a pai... See more

Company replied

Rated 5 out of 5 stars

Barry has consistently been my first port of call for chartering. Ive thrown some easy tasks and some not so easy ones at him and hes always delivered with great boats, at great prices. I know WI will... See more

Company replied

Company details

  1. Boat Rental Service
  2. Travel Agency
  3. Vacation Rental
  4. Yacht Broker

Written by the company

Founded in 1998 within the picturesque Windward Islands of the Caribbean, Windward Islands Yachting and Travel traces its origins to a visionary captain impassioned by Caribbean sailing. Beginning with the establishment of a yacht brokerage office in Martinique, the company burgeoned over the years. Fueled by the founder's infectious enthusiasm and unwavering integrity, the enterprise expanded its reach to encompass various countries, including the USA, Spain, Germany, Italy, Argentina, and China. Evolving into a seasoned entity with over 25 years of maritime expertise, the company boasts a dedicated team of charter and sale brokers, management specialist and yacht marketing experts. The trademarks Windward Yachts and WI Yachts are emblematic of Windward Islands Yachting and Travel's enduring commitment to excellence and integrity.


Contact info

4.9

Excellent

TrustScore 5 out of 5

236 reviews

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Rated 5 out of 5 stars

BVI Catamaran

We booked our catamaran vacation through Barry and everything was extremely seamless. We were bringing our young kids along and one person in our party has sever food allergies and Barry was really helpful communicating with the crew to make sure they would be able to accommodate us. We would gladly use him again!

February 21, 2026
Unprompted review
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Rated 5 out of 5 stars

Windward are a great charter company!

I've used Windward Islands Charter a few times now. I am a recurring customer. I think they are great and save me lots of time trawling through the various charter companies. They always have proactive suggestions about deals on boats and information about charter areas. Barry is a pleasure to deal with and knowledgeable. I've been chartering for a long time and used various companies. Windward are really great company to deal with.

January 17, 2026
Unprompted review
Rated 5 out of 5 stars

Trusted Advisor, Not Just a Charter Broker

Barry’s personal engagement and support were outstanding. He never treated us as just another booking, but as clients he genuinely advised and advocated for. He worked diligently to identify the right charter, negotiated favorable terms, and stayed actively involved to ensure we were fully satisfied throughout. Windward Islands was consistently responsive, clear, and effective in addressing any questions or issues before and during the charter.

February 18, 2026
Rated 5 out of 5 stars

This is the third time we have worked…

This is the third time we have worked with Leslie, Tahiti, Greece and now the Caribbean. She helped us select the boat and once we were set on the boat, everything went as promised. WE will be using Windward and Leslie again

January 24, 2026
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thanks Robert! Always a pleasure to help you on your adventures ;)

Rated 5 out of 5 stars

Book with WI

I would highly recommend booking a trip with Windward Islands. I worked with Barry Price and he was knowledgeable, professional and always responded quickly to any inquiries that I had. He found my group (2 families) the perfect boat. I look forward to booking another trip!

December 28, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thank you so much for your kind words and recommendation. I’m delighted to hear your trip went so well and that the service met your expectations. We truly appreciate your support — it means a lot to a small company like ours.

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Rated 5 out of 5 stars

Unforgettable and Perfectly Planned Trips Thanks to Barry

Barry was absolutely amazing and played such a huge role in making two of our favorite trips ever, one to the Bahamas and one to Tahiti both during NEWYEARS. From start to finish, everything was incredibly organized and so well communicated, which made the whole experience completely stress-free. Every detail was thought through, and we always felt informed and taken care of. On top of that, the people on the boat we chartered were fantastic, and the overall group dynamic made the trip even more special. Thanks to Barry’s planning and coordination, both trips were unforgettable, seamless, and beyond what we could have hoped for. We couldn’t recommend him more!

December 26, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thank you so much for this incredible feedback. We’re thrilled to hear both trips were unforgettable and that the planning helped make everything seamless for you. Your recommendation means a great deal to us and truly helps our small company grow.

Rated 5 out of 5 stars

Windward Islands - simply the best

We have used Windward Island for years know and Barry Has always looked after us very well. He is the very definition of customer service, from finding the right places, to finding the right companies and boats at very competitive prices right to the follow up afterwards. He is very professional and responsive and has recently helped me surprise my husband with a fabulous sailing trip in Guadeloupe. We will definitely be back!

November 10, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thank you so much for your wonderful review. We’re delighted to hear you’ve trusted us for so many years and that your experiences have consistently been positive. Your support and loyalty mean a great deal to us, and we look forward to helping you plan many more unforgettable trips.

Rated 5 out of 5 stars

Sailboat renting in Europa and Caribbean

I have used several brokers for renting sailboats in Europa and the Caribbean. Windward with Barry Price was a very good contact. Very professional, and not least that hi is very quick to find the right boat model, and competitive price. We just used an offer from him in Croatia with success,and are now looking forward to the next booking in December in Antigua. BARRY now the words SPEED TO MARKET.
Using a broker builds trust both ways, and Barry proves it. We look forward to using Windwrad and Barry again.

October 20, 2025
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Reply from Windward Islands Yachting & Travel

Thanks Martin !

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Rated 5 out of 5 stars

I have been with Windward- islands for…

I have been with Windward- islands for over 10 years. They have always given me excellent service, and when there was the occasional problem in the past, they step up to the plate and manage to exceed my expectations. So I can enjoy my holiday charter with my crew while they sort out everything . Ask for Barry, he is a pro.

October 1, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thanks a lot

Rated 5 out of 5 stars

The boat was amazing

The boat was amazing. We had a great sailing. Everything was easy with WI. I appreciated a lot to have always quick responses and full understanding of our expectations. Thanks a lot to Barry Price.

August 8, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thanks a lot !

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Rated 5 out of 5 stars

Perfect trip

Perfect trip. Well organized, everything went as expected.

July 12, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thank you so much Jerome

Rated 5 out of 5 stars

Always friendly and professional.

Always friendly and professional.. have used Barry with all my charter needs for the past 10 years.. I highly recommend him.

July 3, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thanks a lot Ricky!

Rated 5 out of 5 stars

Great organisation

Great organisation, choice and meeting expectation

July 26, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thanks a lot !

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Rated 5 out of 5 stars

Second time I've organised a charter…

Second time I've organised a charter with Barry and both times he's been great.

Always quick to respond and suggests good options.

Fully trust him to get us an appropriate vessel at a decent price.

January 28, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thank you so much

Rated 5 out of 5 stars

Lisa from WI took care of all our…

Lisa from WI took care of all our needs. Communication was spot on .Lisa answered all our questions and provided all our needs.We had everything we needed. The boat YOFF was exactly how it was described with an excellent Captain and Chef. Thank you Lisa for everything.

July 5, 2025
Unprompted review
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Reply from Windward Islands Yachting & Travel

Thank you so much !!

Rated 5 out of 5 stars

Go straight to Barry for your yacht charters!

Barry Price was our agent for two fabulous yachting trips in French Polynesia. Barry is extremely helpful, polite, honest, knowledgeable and reliable. His advice was first class and timely. My friends and I had the trip of our lives!
Go straight to Barry for your yacht charters!

June 20, 2025
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Reply from Windward Islands Yachting & Travel

Thank you so much

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