The Best Caribbean Islands in May – Our Top Two Picks for Shoulder Season in the Caribbean
April showers bring May flowers, am I right? In the Northern Hemisphere, the month of May means the arrival of spring, complete with colorful blooms, warmer weather, and unfortunately, the beginning of allergy season. But way down south in the Caribbean, May means the beginning of shoulder season! With fewer crowds and better prices, this month is an ideal time to visit the Caribbean islands – but which are the BEST Caribbean islands in May? Let’s find out!
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The Best Caribbean Islands in May? Our Pick: Key West, Florida
Think you need to leave the country to enjoy those tropical Caribbean vibes? Think again! Located southwest of continental Florida and north of Havana, Cuba, Key West isn’t actually a Caribbean island. Instead, this lazy little island (just 2 miles by 4 miles!) lies just where the Atlantic Ocean meets the Gulf of Mexico.
The best part? Key West is actually reachable by car via Florida’s Overseas Highway, which connects it to the other Florida Keys and to the mainland itself – making Key West the perfect destination for anyone with a fear of flying (or anyone without a passport!).
Of course, Key West is fairly hot for much of the year, and the summer months can sometimes feel uncomfortably hot and humid. Luckily, May temperatures are typically more pleasant, with highs generally in the mid-80s. Combined with the lower crowds of shoulder season, this month is an ideal time to visit the Florida Keys!
Key West may not be a Caribbean island, but you certainly won’t miss out on those laid-back Caribbean vibes. This famously laid-back locale is known for its free and easy atmosphere, slow pace, and easy-breezy sensibilities.
While Key West isn’t exactly known for its beaches (they’re often rocky and rugged), you’ll find a charming island that boasts incredible snorkeling and diving, interesting history, and a unique and quirky culture that moves strictly on island time.
Key West History & Culture
When you’re not relaxing by the pool or sailing through those turquoise Floridian waters, you’ll spend your days exploring the incredible culture and history of Key West.
Learn about the island’s maritime history at the Key West Shipwreck Treasure Museum, get a glimpse of real-life treasure at the Mel Fisher Maritime Museum, or walk in the footsteps of a literary legend at the Hemingway House & Museum. Looking to merge history with those traditional island vibes? Hop on a boat, ferry, or seaplane and head for Dry Tortugas National Park! This 19th-century fort offers everything from swimming beaches and snorkeling to guided historic tours.
Of course, no visit to Key West is complete without a healthy dose of the island’s vibrant nightlife! For a laid-back evening, make like Jimmy Buffett and kick back with a margarita at Ricky’s Blue Heaven! With its low-key atmosphere and famously funky vibe, this iconic Floridian landmark inspired Buffett’s 1995 track “Blue Heaven Rendevouz.”
Of course, if you’re in search of a more raucous type of fun, head straight for Duval Street! This iconic strip offers a wealth of restaurants, bars, and live entertainment. Be sure to watch the sunset from Mallory Square before joining the party at Sloppy Joe’s Bar, which has entertained guests since 1933.
3. The Bahamas
There’s no bad time to visit The Bahamas – yet the month of May is particularly inviting. With lower crowds through shoulder season and pleasant air and water temperatures, May is a wonderful time to bask in the Bahamian sun and enjoy that tropical romance.
In The Bahamas, there are plenty of luxurious and romantic accommodations to choose from. The famous Atlantis Paradise Island is both opulent and iconic, but with its family-centered vibe, it can also prove a little busy for couples looking for privacy and relaxation.
If peace and quiet are high on your priority list, opt instead for the all-inclusive and adults-only Sandals Royal Bahamian. This elegant beachfront resort includes everything from food and drink to water sports, live nightly entertainment, and even airport transfers. The beaches here are exclusive to resort guests, so you’re guaranteed a healthy dose of much-desevered tranquility.
Vibrant Culture & Heritage
You may want to fill your days with sun-soaked serenity, but what if you’re looking to heat up your nights? You can enjoy the various bars, nightclubs, and shows at your chosen resort, but don’t forget to venture out to soak up that rich Bahamian culture.
The Bahamas isn’t just one of the best Caribbean islands in May for its great weather and low crowds (after all the same could be said for much of the Caribbean!). In May, The Bahamas offers one special event that sets it apart: Junkanoo!
While Junkanoo is typically associated with the holidays and the month of December, this vibrant festival actually occurs twice a year: once in December/early January, and once in late April/early May.
With colorful costumes, joy-filled dance, and a gloriously grand parade, Junkanoo brings together people from all over the globe to celebrate diverse culture of The Bahamas.
Is May a Good Month to Go to the Caribbean?
May is WONDERFUL time to visit the Caribbean! Temperatures are a bit higher than during the winter months and you’re more likely to experience small bouts of rain, but May offers beautiful weather and invitingly warm waters. When you visit in May, you’ll head off the beginning of hurricane season and avoid more severe weather.
Additionally, May is considered shoulder season in the Caribbean, with peak tourist season falling in March and April. This means you’ll enjoy lighter crowds AND lower prices.
What Caribbean Island is Best to Visit in May?
Choosing the best Caribbean islands in May is truly a matter of opinion. May is a great month to visit almost any Caribbean island, so your ideal destination will depend on your personal travel preferences.
If you’re looking for cooler temperatures, choose an island that lies more to the north, like The Bahamas. If nightlife is a priority, Key West will be calling your name! In the end, the RIGHT island for you is the one that calls to your soul.
Which Caribbean Island has the Least Rain in May?
Aruba is known as the driest Caribbean island, which also holds true in May. For the smallest chance of rain, choose Aruba for your romantic May escape. This lively island offers plenty of fabulous beaches and sun-soaked adventures.
Ready to Book A Caribbean Escape This May?
Ready to pack your bags for a romantic Caribbean escape? Whether you’re traveling in May, January, October, or any other month of the year, we’re here to help! Just click below!