7 Caribbean Destinations to Visit This Winter

Choosing the right Caribbean vacation spot isn't always easy. Even though they can all essentially be categorized as archetypal tropical islands, each one has subtle and not-so-subtle differences that can drastically alter the profile of a trip.

This brings up some challenges for the independent trip planner. Most Canadians can barely name all the islands in the Caribbean, let alone recognize their individual distinctions. Putting together a trip to the region that reflects one's travel priorities requires either some dedicated research or some spot-on advice.

Fortunately we can supply the latter. Each of the following suggestions has been catalogued below by the type of experience it is well-known for supplying. Which isn't to say that you can't also find other attractions there as well. Many of the islands can satisfy every type of traveler, from the partier to the outdoorsperson to the culture fanatic to the rest and relaxation-minded.

The attractions we've highlighted are just commonly emphasized in their respective tourism industries.   

1. For the humanitarian: any destination recovering from hurricane damage

No discussion regarding Caribbean holidays during the 2017-18 winter should happen without acknowledging the tragic storms that ravaged the region throughout the fall. This past hurricane season was one of the most vicious in recent memory. Puerto Rico, Barbuda, St. Bart's, Anguilla, the US and British Virgin Islands, St. Martin, and Dominica are all still at various stages on the road to recovery after being hit hard by Hurricane(s) Irma and/or Maria. However, most of them are able to accommodate tourists in some capacity, and even though it may not be the ideal point in time to be there from a visitor standpoint, the tourism and the economic benefits it brings will never mean more to the locals. If you do go elsewhere, consider making a donation to relief efforts.

2. For the foodie: Guadeloupe

Guadeloupe's cuisine is just as unique and exciting as you would expect it to be based on the island's wonderful name. This French territory is best known for its Creole dishes, which mix a wide array of spices with meats, veggies, and local seafood to create flavours that are somehow both distinct and reflective of all sorts of world influences. Even if you've had your fill of local specialties like bébélé, calalou, and féroce, many of the island's restaurants serve food that trends closer to standard North American fare.

3. For the beach lounger: Aruba

Aruba should be at the top of the list for anyone looking to chill out on the beach—and do little else—while they're away. This island has an abundance of world renowned beaches and resorts. The water is stunningly clear, the sand is bright and powdery, and the heat is complemented by a consistent breeze that is difficult to come by elsewhere. It's hard to think of a better place to finally tackle those 14 books you've been putting off for ages.

4. For the party animal: Trinidad

This petite island country probably boasts more partying per capita than any other country on earth (it also includes the comparatively tamer Tobago). Far less tourist oriented than most of the other Caribbean islands, Trinidad has an unrivaled party culture that is distinctly its own. Locals can often be found fetting (full-on partying) or liming (hanging out at a smaller informal gathering) in their free time. The island's celebratory vibe reaches its climax in late winter with a frivolous, bacchanalian Carnival that has been dubbed as "The Greatest Show on Earth." For those looking to go wild in the Caribbean this winter, Trinidad is far and away the best option.

5. For the water sport enthusiast: Turks & Caicos

Not far from the US's southern coastline, Turks & Caicos is a collection of islands that provide a perfect setting for travelers to finally try those water sports they've been fantasizing about for ages—or to keep working at the craft. Diving, snorkelling, kayaking, and paddleboarding in T&C are as good as it gets in the Caribbean. The calm waters and pretty scenery make sure of that. The only drawback is that surfers will have trouble finding great waves.

6. For the cultural connoisseur: Curaçao

A melting pot of Caribbean and European culture, Curaçao is a Dutch state that provides modern day travelers with a wide window into the past. Visitors will frequently come across remnants of Curaçao's thriving mercantile economy. Its capital, Willemstead, has been designated a UNESCO World Heritage Site, and is overflowing with historical buildings and architectural curiosities; including, of all things, the oldest Jewish Synagogue in the Western Hemisphere.

7. For the hiker: St. Lucia

St. Lucia is a picturesque island that boasts two of the world's top hikes. The Pitons are a duo of volcanic mountains that stand well over 700 m above sea level. Once travelers have tackled those two spire-like vertical wonders, they can check out some of the many lush hikes on flatter ground. Or pop over to the nearby Grenada or Tobago, which are also considered to be hiker havens.

Once you decide on your destination...

Settling on a destination is only the first step in executing a smooth winter vacation. Here are a few other things you'll want to be aware of: