I've been to 20 Caribbean islands. These are the 5 I'd return to — and the 2 I'd skip despite having great experiences.

• St. Lucia is home to great wellness activities, fun nightlife, and delicious food.
• Although I enjoyed my time on Grand Bahama, this island left me wanting more.

However, Grand Cayman was one of the priciest islands I’ve visited.

If you want to be closer to the action, I recommend skipping Grand Bahama for New Providence, which is home to top-notch restaurants and hotels, historic landmarks like Queen’s Staircase, and the annual Junkanoo parade.

This story was originally published in May 2024 and most recently updated on July 22, 2026.