Since 2004, Caribbean Winds has been offering first class vacations and experiences throughout the Caribbean. Founded by one man with a passion for kitesurfing and the charm of the Caribbean lifestyle, Caribbean Winds is a travel company unlike any other.

Offering hotel and destination recommendations based upon personal experience, the team behind Caribbean Winds has used their knowledge to forge relationships with hoteliers across the Caribbean and several countries that border the Caribbean Sea, in order to bring you the best variety and value for money.

Working exclusively with TripAdvisor to identify the Caribbean's most awarded and highest reviewed resorts, we work tirelessly to ensure that your vacation booking experience is as smooth and enjoyable as possible. From local information and traveling tips to our own real-time, online concierge, we can recommend the perfect fit for your first, or fiftieth, visit to the Caribbean.

Bring your passion. We'll take care of the rest.



Paul Caswell - President/Owner

Before launching Caribbean Winds in 2004, Paul Caswell had a successful career at America Online, Inc for seven years (1993 – 2000). During his tenure with AOL, Paul developed key products including Parental Controls, Online Polling, and various versions of the AOL software for both Mac and Windows platforms.

After advancing his way up from technical support to product development and eventually management, Paul left AOL to pursue a more southerly track. Combining technical finesse with a penchant for kiteboarding, Paul introduced Caribbean Winds, at that time a travel and reservation system serving the adventure watersport community.

Today, Caribbean Winds has expanded to include beach-loving, Caribbean-bound travelers of all flavors.

When Paul left the American high-tech scene to follow adventures in the Caribbean, he honed his kiteboarding skills and traveled the islands. He served as Vice President of the Professional Kiteboard Riders Association (PKRA), where he competed professionally as well as provided technical and multimedia services for the organization.

While traveling the Caribbean, Paul and his team forged relationships with hoteliers throughout the islands, and have personally visited over 80% of the destinations featured on Caribbean Winds.

Ken Lewis - Technology Manager

Ken has a long history of IT and engineering experience. Born and raised in Jackson, Mississippi, Ken enlisted in the U.S. Navy at age 18.

During his time in the Navy he began his career by attending the rigorous Naval Nuclear Power program as an Electronics Technician. During his career, he was stationed on the nuclear-powered aircraft carriers USS Eisenhower (CVN 69), USS Enterprise (CVN 65), and ultimately returned as an instructor at Naval Nuclear Power Training Command. During this time he was not only responsible for the operation and maintenance of the nuclear reactors in his care, he was also charged with maintaining the computer networks at each of his commands and he also co-authored several computer and web applications used to improve existing processes thereby saving hours of work and millions of dollars.

In 2011 he started his own web development company to test the viability of taking his programming skills commercial. Upon his retirement in 2012 he took his business full-time where he began the development of

Julia Evans - Online Marketing Manager

For over six years, Julia produced graphics and search-optimized content for the websites of some of the UK's largest travel companies, in addition to liaising with home-based travel agents and engaging with customers through social media channels. In 2012, all of the pent-up wanderlust she had acquired during her time at these companies propelled her to embark on an epic round-the-world trip and she hasn't looked back, since forging a new career as a freelancer specializing in the travel sector.

Working to help grow Caribbean Winds into a dynamic new travel brand, Julia has worked alongside Paul and his colleagues to produce content for the website as well as building the social media presence of the company.




"I’ve known Paul, the owner of Caribbean Winds, since we worked together back in the 90’s. Paul is quite the traveler so when I needed help organizing a last minute “25th Wedding Anniversary” trip to someplace relaxing and tropical I sent him an email. After some discussions Paul went to work and quickly got back to us with a 14 page list of recommendations that included three island destinations (Turks & Caicos, St Martin, and Barbados), a range of hotels at each destination, and a listing of the pros and cons of each option. Paul even provided detailed itineraries and recommended airlines for all three islands.

Based on Paul’s recommendation we went to the Turks & Caicos and stayed at the Sibonné Beach Hotel. We weren’t interested in the insulated experience you can get when you stay at some hotels, we wanted an apartment on the beach, a pool nearby, great food and a very laid back vibe. Sibonné was perfect.

We took several snorkeling trip’s, did some paddle boarding, lounged on the beach, drank a fair amount of vodka and rum, and even tried our hand at kite-surfing. Let’s just say that it’s harder than it looks and I was glad to get out of the water! It was an amazing trip and Paige and I would go back again in an instant. Paul and the folks at Caribbean Winds work like old school travel agents and they have ‘boots on the ground' knowledge of the places they recommend. They helped create a 25th Wedding Anniversary trip that was custom tailored for us. I’ll definitely use again."

Bill O'Luanaigh