The Best Time To Visit The Caribbean

Unless you’re from Miami, weather in the Caribbean will feel quite different than the climate you’re used to. Instead of four seasons, these islands operate on two: rainy and dry. 

Dry Season (November–April)

As winter peaks up north, the Caribbean islands hit their high season, and it’s no surprise travelers flock to the islands at this time of year. Temperatures consistently hover between 75 and 90 degrees (Fahrenheit), and rain feels like a distant memory. Perfect weather for snowbirds can bring high prices, though; if you’re on a budget, consider booking in the shoulder season (October to November and April to May). 

Wet Season (May–October)

While your odds of getting caught in an actual hurricane are pretty slim, visiting during the rainy season means you’re nearly certain to get wet at least once or twice. However, a visit to the Caribbean at this time has its advantages; hotels on every island offer deals, and surfers can enjoy truly world-class swells.

Many Caribbean travelers don’t venture beyond the walls of their resorts or cruise ship harbors. For the traveler who’s willing to explore, though, the islands offer incomparable natural wonders.

Marine Life
No matter which island you visit, you’ll find opportunities to explore the ocean with a kayak, snorkel or scuba gear. Whether you’re taking a dip in Dominica’s bubbling Champagne Reef or exploring the glowing bioluminescent bays of Puerto Rico and Vieques, you’ll likely find the clearest waters during the dry season (November to April) as summer storms often stir up sediment that can obscure your views. If you’re in Dominica or the Dominican Republic between January and March, you might even run into one of the hundreds of humpback whales that migrate to the island each year!

Waterfalls
The Caribbean’s waterfalls are one attraction that’s arguably more spectacular in the rainy season. There’s something truly magical about emerging from a misty rain forest to a thundering waterfall flush with rainwater. Puerto Rico’s La Mina, Dominica’s Emerald Pool Falls and Jamaica’s cascading YS Falls are some of our favorites. While they’re breathtaking year round, they’ll be at their fullest from June to October.

No matter when you visit, your trip to the Caribbean will be spectacular. If you plan your vacation around one of the islands’ many festivals, though, you’ll have an experience that’s truly one of a kind.

Carnival
Colorful parades. Handmade headdresses. Free-flowing rum. Carnival is a little bit different on every island, but regardless of which event you hit, it promises to be the party of a lifetime. Trinidad’s festival in late February is our current ranking champion for the most raucous event; for a more family-friendly carnival, head to Curacao for a monthlong festival that peaks in early March.

The Caribbean’s main attractions are natural, so you’ll rarely encounter the types of crowds that amass at the Mona Lisa or the Sistine Chapel. However, seasonal spikes in tourism mean some parts of the year are more crowded than others. If you don’t mind a bit of company on your beach, book your trip during the high season (November to April); if you’d prefer a bit more solitude, consider a trip in the shoulder season of October to November or April to May. 

After enough time in paradise, you might find yourself getting antsy for an adventure. Fortunately, each island offers a multitude of options.

Surfing
We’re not sure what’s better about surfing in the Caribbean: perfect breaks for surfers of all skill levels or the ability to lie on a picture-perfect beach after an exhilarating morning of catching waves. Puerto Rico, the Dominican Republic and Barbados have some of the better-known breaks. Generally, each island’s Caribbean coast has calmer waters, while the Atlantic side is better for experienced surfers. While the biggest swells arrive in July and August, calmer waters from November to April still challenge all but the most-seasoned surfer.

Hiking
The mountainous interiors of the Caribbean’s larger islands offer fabulous hiking opportunities. Viñales in Cuba, El Yunque in Puerto Rico, the Blue Mountains in Jamaica and the region around Jarabacoa in the Dominican Republic are some of our favorites. If you’re looking for something more off the beaten track, check out Dominica in the eastern Caribbean, and discover why it’s called the “nature island.” These trails are spectacular at any time of the year, but be aware of frequent rain and mud during the wet season (May to October).

Dancing
For dance lovers, the Caribbean is one of the world’s greatest destinations. Want to feel as if you’re in a music video? Look no further than La Factoria in San Juan, where they filmed the music video for global mega-hit “Despacito.” Steel drums more your thing? Check out a local bar in a laid-back island, such as Barbados or Grenada. Looking for something on the traditional side? The classic salsa clubs or the street parties along the malecón in Cuba will have you feeling as if you walked onto the set of Dirty Dancing: Havana Nights! The best part? Islanders love to dance at any time of the year, so this party never stops!

Backroads offers numerous ways to experience the very best of the Caribbean on our award-winning active travel adventures. Explore this region in the best and most genuine way possible—away from the crowds, buses and tourist hot spots. We hope you'll join us! Check out our full list of Caribbean adventures here.

Want to learn more about the Caribbean, including its history, travel tips, highlights and insider info?

Check out our full Caribbean Travel Guide!