So, you’re thinking of a spring tropical getaway but can’t decide where to go? In this blog, we take a look at the 8 best Caribbean islands to visit in May, giving you an insight into what vibe to expect and what type of traveller each island is suited to. Whether you’re an eco-conscious nature lover or are searching for ultimate luxury where you can kick back and relax – you’ll find it in this blog.
Is May a Good Month to Visit the Caribbean?
Yes! May is the perfect time to visit the Caribbean. Peak tourist season finishes in March/April, meaning the crowds have died down. Also, the temperature is starting to climb again, meaning the water temperatures have lost their chill, and the ocean is more like a bath. Honestly, May probably has the best conditions for a Caribbean vacation. And, as May falls in the shoulder season, you’ll find more accommodation choices and potentially better rates too.
8 Best Caribbean Islands to Visit in May
1. Antigua
With 365 beaches (one for every day of the year), Antigua is a beach-lovers dream destination. And it’s pretty popular with sailors too. During the month of May, the island comes alive with plenty of events, particularly Antigua Sailing Week and Antigua Restaurant Week.
If none of those events takes your fancy, Antigua is still one of the best Caribbean islands to visit in May because you can make your trip here whatever you want it to be. Circumnavigate the island, stay in your resort, head to the beach (we recommend Morris Bay and Darkwood Beach), get out on the water, enjoy some of the best snorkelling and diving, get involved with some nightlife and parties at places like Shirley Heights, and much more.
🏡 Find: Places to stay in Antigua
🎒 Find: Excursions & things to do in Antigua
2. St Lucia
Often touted as a dream destination for couples and honeymooners, St Lucia is actually much more than that. On this small mountainous island, you’ll find the perfect combination of relaxation, luxury (especially at resorts like Jade Mountain), and opportunities to explore. A big reason to visit in May is St Lucia Jazz and Arts Festival. It kicks off at the end of April and runs until May 11th 2025. This event has been running for over 30 years and is the most sought-after arts festival in the entire Caribbean.
We think St Lucia is one of the best Caribbean islands to visit in May for those who want to experience the real Caribbean, with a side of unlimited luxury. The lush rainforests are full of beautiful waterfalls, sulphur springs, mud baths, cocoa plantations (we recommend the Tree to Bar Experience), mountains and the UNESCO Pitons for hiking, and much more. Alternatively, if you’re looking for all-inclusive, relaxing luxury, you’ll be able to do that in one of the many incredible resorts, or on the beautiful beaches in St Lucia.
🏡 Find: Places to stay in St Lucia
🎒 Find: Excursions & things to do in St Lucia
3. Dominica
If you ask anyone who has visited Dominica, they will tell you that it is their favourite Caribbean island. This eco-conscious island is dedicated to protecting its environment, and once you see this place, you’ll know why. The landscapes here are like the stuff of dreams, lush rainforests and waterfalls, the 2nd largest boiling lake in the world, flowing rivers and jaw-dropping beaches that remain untouched by any form of mass tourism. You won’t find resorts here. That’s not what Dominica is about. What you will find is a traditional, quintessential Caribbean experience that is like stepping back in time.
Undoubtedly, Dominica is the best Caribbean island to visit in May for travellers looking for an off-the-beaten-path experience. If you’re a nature lover who can pass up on the luxuries in favour of once-in-a-lifetime experiences, then Dominica should be on your list of vacation destinations. Also, in May, you’ll be able to join in the Jazz and Creole Festival celebrations in true Caribbean style.
🏡 Find: Places to stay in Dominica
🎒 Find: Excursions & things to do in Dominica
4. Aruba
As part of the Dutch Caribbean, Aruba sits in the southernmost part of the island chain. It’s long been a dream destination for many, and plenty of tourists come here year-round to experience its incredible beaches and blend of Dutch, Latino and Caribbean cultures. This incredibly popular destination is well-prepared for tourism, with plenty of choice when it comes to accommodations, including private rentals, boutique hotels and luxury resorts.
One of the reasons Aruba is one of the best Caribbean islands to visit in May is the Hi-Winds international windsurfing competition, but aside from any May-only events, Aruba is the ideal destination anyway. There’s something for everyone. You can get out on ATV tours, horseback tours, boat trips, sunset sails, bar hopping nights, and so much more on this paradise island.
🏡 Find: Places to stay in Aruba
🎒 Find: Excursions & things to do in Aruba
5. Barbados
There’s never a bad time to visit Barbados (except maybe September when a lot of places are closed for refurbishments). We think Barbados is one of the best Caribbean islands to visit in May for those people looking for a home away from home experience with sensational beaches, impeccable service and a laid-back vibe. The selection of resorts, hotels, accommodations and restaurants are what make Barbados stand out. It’s the most developed of the eastern Caribbean islands and is the most well-equipped island for hosting tourists.
One of the great things about Caribbean culture is the music. In May, Gospelfest is hosted in Barbados. And you’ve also got Oistins Fish Fry every Friday, where you’ll find great music and incredibly tasty Bajan cuisine. But there are plenty of other things to do away from beaches, restaurants, Gospelfest and Oistins. Although Barbados is a flat island, if you go out and explore you’ll find some pretty stunning landscapes, especially along the east coast and around Bathsheba, and inland, you’ll find tropical gardens like Hunte’s Garden, lush gullies and Harrison’s Cave. We absolutely recommend renting a car in Barbados to explore the best of the island.
🏡 Find: Places to stay in Barbados
🎒 Find: Excursions & things to do in Barbados
6. Grenada
Grenada is in our top 3 favourite Caribbean islands. It has the beaches of Barbados and the landscapes of St Lucia, coupled with the friendliest culture and locals we’ve experienced. Nicknamed the spice island, Grenada is home to plenty of cinnamon and nutmeg plantations, but what you might not know is it’s famous for its chocolate and cocoa plantations too! And in May, it’s Grenada Chocolate Festival, where numerous chocolate-related events take place across the island.
But, while the chocolate is incredible, it’s not why I think Grenada is one of the best Caribbean islands to visit in May. Genuinely, Grenada has everything: beaches, waterfalls, lakes, mountains, hiking, luxury resorts, incredible (and affordable) restaurants, and an infectious vibe that just makes you want to smile.
🏡 Find: Places to stay in Grenada
🎒 Find: Excursions & things to do in Grenada
7. The British Virgin Islands (BVI)
Made up of islands, reefs and cays, the British Virgin Islands is an island-hopping paradise that’s a favourite with sailors from around the world. In this region, you’ll find some of the most breathtaking snorkelling, diving and beaches you’ve ever seen. As a first-time visitor, we’d recommend basing yourself on the main island, Tortola. This gives you the perfect base to catch ferries and explore the other smaller islands, such as Virgin Gorda, Jost Van Dyke and Anegada.
The reason the BVI is one of the best Caribbean islands to visit in May is the weather and the fact that the tourist season has calmed down a bit. It’s the perfect time to get out on the water sailing. A great way to experience the BVI is by chartering a boat. This gives you the freedom to explore rather than being tied to ferry schedules, which can be confusing.
🏡 Find: Places to stay in the British Virgin Islands
🎒 Find: Excursions & things to do in the British Virgin Islands
8. Anguilla
Anguilla is a hidden gem in the Caribbean that you’d describe as understated elegance and untouched natural beauty. Unlike the crowded tourist spots found on some other islands, Anguilla provides a piece of paradise where, on most days, you’ll enjoy the luxury of having the beach all to yourself!
Famous for its food and incredibly warm locals, Anguilla offers something a little different to all the other countries on the list of best Caribbean islands to visit in May. It’s often known as the culinary capital of the Caribbean and, in May, the Anguilla Culinary Experience takes place. From April 30th – May 4th, some of the best restaurants and resorts come together for a showcase of flavours. So, if you’re a foodie, Anguilla is definitely up there with the best Caribbean islands to visit in May. Also, on May 30th the island celebrates independence on Anguilla Day with loads of events from street parties to boat races.
Not forgetting the gorgeous coastline, where you’ll find expansive sandy beaches such as Rendezvous Bay, which offers views of the nearby island of Saint Martin, to hidden coves accessible only by boat or kayak, like those found at Little Bay.
If you like the finer things in life without feeling pretentious, Anguilla is an ideal choice for a Caribbean island to visit in May.
🏡 Find: Places to stay in Anguilla
🎒 Find: Excursions & things to do in Anguilla
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What is the weather like in the Caribbean in May?
In May, the Caribbean enjoys warm and sunny weather, with temperatures typically ranging from the mid-70s to mid-80s Fahrenheit (around 24-30 degrees Celsius). While there may be occasional rain showers, the overall climate is warm yet bearable, making it the perfect time to visit the Caribbean.
Is May tourist season in the Caribbean?
May marks the transition from the peak tourist season to the shoulder season in the Caribbean. While tourist numbers may have decreased compared to the busy months of March and April, May still sees a steady flow of tourists. This shoulder season often brings fewer crowds and potential discounts on accommodations and activities, making it an appealing time to visit for those seeking a more laid-back experience. On the plus side, all restaurants, resorts and activities will still be open.
The Best Caribbean Islands to Visit in May Summarised
Overall, we think May is one of the best months to visit the Caribbean. The crowds have subsided, the temperatures are bearable, the water is bath-like, and you’re almost guaranteed to have an incredible time wherever you go. No matter which island takes your fancy, you’re going to have the experience of a lifetime, and you’ll probably want to come back to the Caribbean at the same time every year.
The Best Caribbean Islands to Visit by Month
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