7 Best Caribbean Islands To Visit In May (2024 Reviews)

December to mid-April is considered the peak season for a holiday in the Caribbean. May is ideal if you want to experience a mix of what the low and high season feels like. There won’t be crowds, but the streets will not be empty in the best Caribbean islands to visit in May. 

When you book a Caribbean vacation in May, there’s also a good chance that you’ll be able to get good discounts.

The weather in the islands is pretty steady all year round, with an overall low risk of rain. The region experiences lows of mid-70 degrees Fahrenheit and highs in the mid-80s. 

If you’re planning to travel in May, here are some of the best destinations in the Caribbean:

#1 Curaçao 

Best Caribbean Islands To Visit In May - Curacao

Curaçao is one of the best off-peak destinations if you’re planning a spring or summer getaway. The former center of the slave trade in the region is now an independent state with a very diverse culture. Such influences show in the language, food, and music.

One of the best Caribbean islands to visit in May, Curaçao receives a minimal amount of rain during the period. With temperatures between 78°F (26°C) and 89°F (32°C), the island is a tropical paradise for anyone seeking to escape the tiring daily grind.

Must Do: Curaçao has so much to offer. From Christoffel Park for those who want to experience a slice of nature, immerse in local culture at downtown Willemstad, traverse the Queen Emma Bridge, to relaxing on one of the beautiful beaches, and enjoying the sunset while on a Caribbean boat tour. As the locals say, it’s always dushi or nice in Curaçao. 

#2 St. Lucia

Save yourself from expensive room rates in this Caribbean paradise between December and April. If your schedule allows for some flexibility, May is perfect for enjoying the breathtaking beauty of St. Lucia. 

Visiting St. Lucia in May gives you the full benefits of the shoulder season. There’s a good chance you can get better deals for your airfare and accommodations during this time. Plus, the weather is great in the mid-70s to 80s. The beaches are less crowded, too, so you can quietly appreciate the pristine and bountiful island on the edge of the Caribbean.

Must Do: When in St. Lucia, you cannot miss experiencing the majestic Pitons, a UNESCO World Heritage Site. There’s also the Tet Paul Nature Trail, Sulphur Springs Park in Soufriere, Anse Chastanet, Marigot Bay, and a good dose of snorkeling, diving, and watersports.

#3 Grenada

This small island in the Caribbean is just 131 sq. mi. but has a rich history, lush landscape, and picture-perfect beaches to offer. 

If you’re planning to book your Grenada vacation in May, you’ll love the tropical climate eased by the trade winds. During this period, rain showers are brief, and you’re holidays won’t be ruined by hurricanes that usually pass through between July and November.

This tourism mecca is popular for its beaches, carnivals, and spices.

Must Do: The Grande Anse tops the list of travelers who want to experience island life. Don’t miss the Grand Etang National Park, Grenada Underwater Sculpture Park, and the build-up for the Grenada Carnival that usually kicks off around April. There are also great deals offered by all-inclusive resorts such as the Sandals Grenada Resort & Spa Grenada.

#4 Anguilla

Best Caribbean Islands To Visit In May - Anguilla

If you’re dreaming of soaking up the warmth of the tropical sun, walking on white sand beaches, and enjoying crystal clear waters, you can never go wrong with Anguilla as one of the best Caribbean islands to visit in May. 

The climate in this corner of the Caribbean is temperate and humid all year round. The average temperature gives you comfortable weather at 70 to 80 degrees Fahrenheit in May. There’s a very small chance of rain and strong winds, guaranteeing you can make the most of your vacation.

For those closely watching their budget, the off-season rates of villas and hotels in Anguilla start in May. You can pretty much stretch your hard-earned cash to satisfy your wanderlust.

Must Do: The picturesque beaches of Meads, Shoal, and Rendezvous Bay should be on top of your list. You can also head to Scilly Cay and other off-island cays that offer different vibes. Of course, don’t forget to immerse yourself in the local food scene.

#5 Cayman Islands

When you visit the Cayman Islands in May, you can take advantage of the warm weather just before the rainy season kicks off in June. The typical day will give you 74 to 90°F weather with short bursts of rain on some days. 

You can enjoy enviable hotel rates in this world-famous diving destination during the period. You can get up close with the thriving sea life if you’re an avid diver, sightsee on one of the islands, or just relax on one of its post-card-worthy beaches.
Must Do: Lounge on the crescent-shaped Seven Mile beach, check out Stingray City in Grand Cayman, discover George Town, and kayak at night at the Bioluminescent Bay.

#6 Puerto Rico

This island nation is just a thousand miles off Florida and is hugged by the Atlantic and the Caribbean. May is one of the sweetest spots if you’re planning a holiday in this U.S. territory. Most days, the weather is pleasant, with temperatures playing in the mid-80s.

Aside from the tropical climate, Puerto Rico is a popular Caribbean destination because of its rich history, diverse landscapes, and colonial architecture.

Must Do: Check out the El Morro, Calle del Cristo, and other iconic sights at Old San Juan. Discover the natural wonders of Puerto Rico by joining a tour of the El Yunque Rainforest. For some fun in the sun, head to Flamenco Beach. Ah, don’t forget to try their rhum.

#7 Martinique

The weather in Martinique in May gives you an average temperature in the mid-70s and mid-80s and an average precipitation of 4.85 inches. This means you have the perfect weather to explore this beautiful island and dive into its culture just before storms hit the region starting in June.

What’s more, you get to discover Martinique sans the touristy peak-season crowd.

Martinique is a little slice of France with an overload of blue sky, greeneries, and white sand beaches.

Must Do: Whether traveling solo or on a family holiday, you can relax at the most beautiful beach in Martinique– the Grande Anse des Saline. You can also scale the heights of Mont Pelle, an active volcano. There’s also the Balata Gardens, Habitation Clement, Diamond Beach, and more.


The Caribbean has many gems to offer, and the best islands to visit in May mentioned above are just a small chunk of that list. With great weather, it will all boil down to what kind of vacation you want and what you want to try.  Go ahead and book that plane ticket and accommodation today. Of course, there’s always a next time to try the other Caribbean destinations.

About The Author
Randell was born in an island nation and is a creature of the water and sun. Aside from amazing Caribbean destinations, he is also fascinated with the region's food, history, culture, and adventures it offers.

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