10 Caribbean Islands to Visit in May, From Antigua and Barbados to Up-and-Coming Spots Like Carriacou and South Caicos

May changes how the Caribbean feels in a way you notice almost immediately. Flights are easier to find, restaurants start to open up, and you don’t need to plan your day around what’s already full. What replaces that pressure is something more useful: time and room to move through each place at your own pace. You can land, get to your hotel, and start the trip without waiting for anything.

It’s also a month where timing works differently depending on the island. In some places, it’s about food, with restaurant weeks stretching across entire coastlines and pulling you from one table to the next. In others, new flights make a noticeable difference, turning what used to be a longer, layered trip into a direct route. And in a few places, May simply means fewer people in the same landscapes—same beaches, same water, just more space.

You end up spending more time doing the parts of the trip that count: being in the water, sitting down for longer meals, and staying out later without thinking about what comes next.

Here are 10 islands where May lines up especially well, and where to go when you get there.

Antigua

May in Antigua revolves around the table. Antigua and Barbuda Culinary Month gives you a built-in reason to get out across the island, whether that means a long lunch near the water in English Harbour or a more formal dinner in St. John’s after an afternoon on the beach. You can spend the day at Valley Church or Darkwood, brush off the sand, and head straight into the evening without much effort. That’s what makes Antigua work so well in May: the beach day and the dinner reservation feel like part of the same plan. You’re not choosing between them.

If you want a contemporary resort with plenty around you, Hodges Bay Resort & Spa gives you a sleek home base, several food and drink options including the new Katsuya, and its own small offshore island. If the better fit is adults-only and quieter, Hammock Cove Antigua is the stronger call, with standalone villas, private plunge pools, and a dining program that can carry the whole stay without wearing thin.

Karen Udler

Karen Udler is the Deputy Travel Editor of Caribbean Journal. A graduate of Duke University, has been traveling across the Americas for three decades. First an expert on Latin American travel, Karen has been traveling with CJ for more than a decade. She likes to focus on wellness, luxury travel and food.