With their turquoise waters, idyllic beaches and balmy temperatures, the Caribbean Islands are teeming with tourists during the winter. Why not skip the crowds and travel in the shoulder season instead?

Caribbean Holidays

Although many avoid travel to the Caribbean during the fall out of fear of hurricanes, this only applies to certain islands. In fact, there are several islands in the Caribbean archipelago which experience little rain during typical wet seasons and have a low risk of hurricanes to boot.

By booking your trip for the fall, you can skip the annoying crowds, get amazing deals and sneak in one final beach vacation before the year is done. So, are you ready to pack your oversized beach towels and soak up the glorious, Caribbean sun? Take your pick from one of these Caribbean destinations that are year-round tropical paradises.

  1. Barbados

With its excellent surf, shimmering sands and historic architecture, Barbados is a truly idyllic island that attracts beachgoers from all walks of life. The most easterly of all the Caribbean islands, Barbados also manages to escape the wrath of most hurricanes, experiencing only tropical storms.

If you visit Barbados, consider renting a car to get around the island and explore the distinct personalities on each side of the coast. Though you’ll find calmer waters on the west coast (as well as pricier hotels), the south coast is fantastic for surfing and has excellent beachside amenities.

  1. Grenada

Want to “spice” up your Caribbean vacation? Check out Grenada, also known as the “Spice Isle” for its wide variety of spice exports, with nutmeg being the island’s largest export. Grenada is actually a tri-island state, made up of Grenada itself, Carriacou and Petite Martinique.


Located just south of the Atlantic’s hurricane belt, Grenada also manages to sidestep most hurricanes. Even during its rainy season (June to December), rainfall typically doesn’t last more than an hour, so you can enjoy the island’s beautiful waterfalls, crystal waters and unspoiled landscapes in relative dryness.

  1. Curacao

If you love diving and snorkeling, you’ll definitely want to book a trip to Curacao. This Dutch Caribbean island is teeming with marine life and serves as the gateway to popular diving sites such as Klein Curacao and Tugboat.

Most people have never even heard of Curacao, which only adds to its mysterious charm. It’s a hidden gem that appeals to not only casual sunbathers, but also water-lovers and adventure-seekers. Of course, it also helps that this tiny yet spirited Dutch island is super friendly and welcoming to visitors.

  1. Aruba

Just north of Venezuela, Aruba is one of the driest islands in the Caribbean and experiences a rainfall of less than 20 inches a year on average. During the fall, you’ll get to enjoy the Dutch island’s year-round sunny skies, sugar-white sands and Instagram-worthy landscape without stressing too much about hurricanes (the last one to hit the island was Omar in 2008).

On Aruba, you aren’t limited to the island’s gorgeous beaches (although, if you want to spend the majority of your time there, no one would blame you). Aruba also boasts tons of sightseeing opportunities, from its historical churches to natural attractions such as the Ayo Rock formations. Rent a car, zip around the 21-mile-long island and be sure to take in all Aruba has to offer.

  1. Bonaire

Known for its dedication to nature preservation and marine wildlife, the small island of Bonaire is a haven for nature lovers and water sports enthusiasts alike. In fact, the island is frequently known as “Diver’s Paradise” for its abundance of public dive sites (86, if you’re wondering) and unsurpassed beauty.


You’ll find these coveted dive and snorkeling spots at Bonaire National Marine Park (BNMP), the oldest marine reserve in the world. The park also provides spots for kitesurfing, sailing and windsurfing.

If you’d rather spend your days lounging on the beach, don’t worry—you’ll have your pick from 22 gorgeous beaches. When you’re tired of the white sands on Eden Beach, head north over to Boka Kokolishi to enjoy the black sands at Washington-Slagbaai National Park.

  1. Vincent & The Grenadines

Ah, St. Vincent and the Grenadines, the quintessential tropical paradises. With their sparkling waters and white sands, this secluded chain of Caribbean islands has long been a hotspot for millionaires and honeymooners. Best of all, the islands haven’t been ravaged directly by hurricanes since 1955, making it a safe bet for fall travel.

Sandwiched between St. Lucia and Grenada, this small set of Caribbean isles is steeped in history and is the perfect playground for adventure-seekers and history-lovers alike. From hiking to the gorgeous Falls of Baleine to exploring the long history of English and French colonialism, the main island (St. Vincent) is packed with activities. For more scenic views and unique history, be sure to explore the other islands via the plentiful taxis throughout the isle.

  1. San Andres

Another secluded, Caribbean island, San Andres falls outside the hurricane belt and is part of Colombia. The tiny, coral island is known for its plentiful reefs, reggae music and lovely stretches of white sand beaches. For a day of shopping, beach activities and delicious food, check out Spratt Bight beach on the north end of the island. Want to go snorkeling in seclusion? Less than a mile away is Johnny Cay Island, which features a staggering number of coral reefs and marine sea life.

Quick Tips Before You Go

Once you’ve chosen an island, the next steps are easy. Before you start booking flights and packing your getaway bag, here are a few tips to keep in mind:

  • Get Travel Insurance: Before you book flights or hotels, make sure that you carefully read the cancellation policies for each. Consider getting travel insurance in case a hurricane hits the island.
  • Be Safe: In terms of safety, not all Caribbean islands are created equal. Play it safe by checking for any U.S. travel advisories so that you can be on high-alert if necessary.
  • Choose Suitable Clothing: Though the dress code varies from island to island, beach clothes for women typically include swimsuits, shorts, cotton t-shirts and coverups made from lightweight fabrics. For the guys, some vacation essentials might include swim trunks, light-colored t-shirts, chino shorts and casual sports shirts that wick away moisture.

Relax, Unwind and Enjoy the Caribbean

With their long stretches of white sand beaches, shimmering waters and gorgeous, year-round weather, each of these Caribbean islands is the definition of a tropical paradise. Though you might get a little rain on some of these islands (it is the wet season, after all), it shouldn’t last long enough to ruin your daily activities. As long as you take certain precautions before you book your trip, you can enjoy these islands in total relaxation.

This post was created in collaboration with Southern Tide.

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