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Island Escapes: Explore The Unforgettable Caribbean

Updated: Apr 7

Ann Phelan September 12, 2024






Why I love sending friends, family and clients to the Caribbean? Firstly, I love the Caribbean. Each island reveals a different experience. Visiting the Caribbean offers a blend of stunning natural beauty, vibrant cultures, and diverse experiences that make it a top travel destination. A three to four hour flight brings you to the islands. The diversity provides a unique experience for all.


My first trip was in 1987! My mom and I flew to the sunny island of Antigua, known for having 365 beaches. We hired a car and drove all over, exploring the countryside, visited historic sights and sampled local cuisines. The beaches were magnificent with gin clear water and white powder sand. I loved it so much I came home, packed two suitcases and moved to the island. That was the start of my Caribbean life. I had a professional career but became a Caribbean Destination Specialist sending hundreds of vacationers to the islands. It's been a labor of love. Here are my favorite islands and why you should visit in 2026!


  • Saba - amazing hikes and diving plus can be combined with a dual island stop including French St. Martin or St. Barths!

  • Antigua for 365 majestic beaches, historic sites and amazing cuisines

  • Puerto Rico for salsa, a rain forest, Latin culture and cuisine

  • Grenada for waterfall and hikes and local West Indian cuisine

  • Anguilla for 33 beaches, seaside reggae bars and water sports galore






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