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The Best May Vacations

23 May

The Best May Vacations

The month of May is a terrific time to book a tropical getaway. It’s a few months after the busy holiday season, but not quite summer yet, meaning we could all use a little break from our daily responsibilities. It’s time to kick your feet up and relax! So, what are the best May vacations?  

If you’re craving tropical vibes, there’s no better Spring destination than the beautiful Caribbean Islands! The weather is perfect, the streets aren’t overly crowded, lodging is often cheaper, and there’s something for everyone to enjoy– from thrilling wildlife encounters to spending hours relaxing on the sandy beach. 

Continue reading to know what to expect and where to go when taking a May vacation in the Caribbean. 

Is May a Good Time for a Caribbean Vacation? 

In the beautiful spring season, May is an excellent time to book a trip to a Caribbean destination. Not only is the weather ideal, but flights and travel expenses should be more affordable because it isn’t the Caribbean’s busy season.  

What is May Weather like in the Caribbean? 

Like most months, May is sunny and warm in the tropical Caribbean region. June is the official start of the wet season, so there’s a chance you’ll experience some rain, especially if you visit at the end of May. However, that should be your only concern. Severe weather is unlikely, and the average temperature is 75 to 85 degrees F– The perfect weather for outdoor adventures and long relaxing hours lounging on the beach! 

Is May a Busy Month for the Caribbean Islands? 

The Caribbean Islands host the most visitors in the winter months when people who typically experience chilly weather crave a tropical holiday season instead. The time of year the islands are especially quiet is during the Caribbean’s rainy season, better known as hurricane season. You can probably guess why this time is not desired tourists. Not only are rain showers and thunderstorms getting in the way of your outdoor adventures but there is always the possibility of a disastrous hurricane striking from June to October. 

May is a great month to visit the Caribbean Island to avoid the chaotic crowds and the chance of severe weather. It is right on the edge of the rainy season, so you may catch a rainy day here and there. For the most part, these tropical islands are perfect for May vacations. 

Are There Special Caribbean Events in May? 

Depending on when you choose to take a tropical trip in May, you may get the chance to experience the region's traditional events and culture-rich celebrations. For instance, the Grenada Carnival starts in April, meaning smaller events are likely scheduled at the beginning of May. Carnival is an exciting, vibrant, and joyous holiday for the Caribbean Islands and countries all over the globe. Celebrations often include lively parades, dancing, colorful costumes, drinks, and delicious local dishes. 

Other must-see events include: 

  • Grenada’s Crop Over Festival May through August 
  • The Chocolate Festival in Grenada 
  • St. Maarteen’s Carnival celebration from April to May 
  • Batabano in the Cayman Islands during the first week of May 

Is it Expensive to Visit the Caribbean in May? 

The Caribbean is a great place for some of the best May vacations, not only because of the tropical vibes. May is also an ideal time to travel to the region because costs are more affordable, including travel expenses, hotel and resort stays, excursions, tours, and more. 

It’s not the cheapest month of the year, but it’s also not the most expensive. The ideal weather in winter draws the most tourists, making it the most pricey time to travel to the Caribbean. And the cheapest season is June through November because of the potential for severe weather and extremely high outdoor temperatures. May falls right between the two, making it budget-friendly for most travelers. 

The Best May Vacations in the Caribbean 

1 | Get Festive in Grenada. 

If you’re searching for a tropical island where you can fully immerse yourself in a unique culture and experience another way of living, Grenada is one of the best May vacations you can book! This gorgeous Caribbean island is very active during this spring month, from the annual Chocolate Festival to the Crop Over Festival.  

When you take a May trip to Grenada, you can expect to make unforgettable memories of experiencing the island's vibrant culture. Besides the exciting Spring events, Grenada is known for its tasty food, wondrous underwater exploration, and sandy beaches. 

2 | Dive into French-Inspired Culture in Martinique. 

For a unique Caribbean experience, choose a week in May to travel to Martinique. The Caribbean region has a diverse history with influences from many cultures, like Spain, Great Britain, France, and America. Martinique stands out with its heavy French influence and traditional Caribbean culture, making for a fascinating, one-of-a-kind May vacation.  

Relax on breathtaking beaches, hike along an active volcano, explore the lush landscape, and dive into crystal-clear jewel-toned waters. And before you return home, don’t forget to taste some of the island’s signature dishes, like flaky grilled snapper with flavorful creole sauce.  

3 | Soak Up the Spring Sun in Anguilla. 

One of the best May vacations is a dreamy trip to tropical Anguilla! May is the start of this island’s off-seasoning, which means the deals and discounts are in full swing. Keep an eye on hotel rates, flight prices, and excursion costs, and you’ll find plenty of budget-friendly options.  

Of course, Anguilla has gorgeous coasts with powder-sand beaches perfect for afternoon strolls and getting the best view of the warm Caribbean waters. Some of the best beaches are Meads and Rendezvous Bay. But the island is also home to world-famous coral reefs teeming with sea life. It’s an excellent opportunity for diving or snorkeling and seeing rare underwater creatures among thriving corals. 



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