Caribbean Contessa, LLC is a leader in destination management travel companies and Caribbean travel advice.


Prior to launching Caribbean Contessa, LLC, Kelly R. Durham, "The Caribbean Contessa", founder and CEO, spent her career practicing law, real estate, and as a contract lobbyist. Her career choices, along with her deep love of the islands, led her to years of first-hand experience in life and travel in the Caribbean. Her research and her extensive knowledge came together in her tried and true weekly ezine entitled, "The Island Lover's Guide to the Caribbean".
Kelly began publishing her ezine to share her years of Caribbean travel experience and enable others to capture the incredible spirit of life in the Caribbean. She had no idea what would soon unfold. The number of subscribers to the ezine increased very rapidly, and those readers began to ask for more-MUCH MORE! Requests for detailed maps of the islands; recipes for Caribbean cuisine; recipes for Caribbean cocktails; book recommendations; deals for group travel; tips on places to stay; flight routes; tips on purchasing a home in the Caribbean; tips on how to start your own business in the Caribbean, requests for a Caribbean forum specifically for the newsletter subscribers, education on the variations in Caribbean spices, fruits, vegetable, fish, etc., and they wanted these items addressed ALL IN ONE PLACE!

Well, you asked for it, and you got it! In response to the overwhelming number of requests, Kelly, along with her awesome team, launched what has now become known as one of the top Caribbean destination management businesses online!

Gone are the days of searching endless internet sites to find the information you need regarding the Caribbean. With the CARIBBEAN GUIDE ONLINE, you have one-stop shopping for “everything Caribbean”!

In addition to providing endless tips and strategies on all facets of Caribbean life, Caribbean Contessa, LLC also customizes hundreds of group tours throughout the Caribbean, Belize, Mexico, Costa Rica, and Panama. With Caribbean Contessa, LLC, there are no "set itineraries". The clients express the desires, interests, pace, and style of each group, and together, Caribbean Contessa, LLC team members and the clients develop the itinerararies that showcase all the islands have to offer!

Our team aggregates and screens the very best group travel options from hundreds of Caribbean providers, with whom they have formed strong and trusting professional ties. The trips are always developed based upon the needs of the client and the team desire to inspire Caribbean travel with a focus on smart luxury value.

So, try us out and let us know what you think. We are always looking for ways to improve our offerings for you, our valued clients!

502-931-8545