I’ve been fortunate to travel widely across the Caribbean over the last 30 years. I’m also a descendant of Caribbean people, so many folks assume I’ve visited every island. Not likely—the Caribbean consists of 28 islands encompassing just over one million square miles. So while I’ve visited most, there are still a handful I’ve yet to encounter. But that’s a good thing. Many know the Caribbean for its picture-perfect views—all lush green hillsides, soft beaches, sunny skies, sun loungers, and poolside cocktails. But that’s really just the white-sandy surface of this region, where each island has something distinct to offer. On Dominica, hiking is unmatched, notably its Boiling Lake, a flooded fumarole located in Morne Trois Pitons National Park, where you can traverse across the rim of an active volcano. The best island hopping is in the British Virgin Islands, while Barbados is the action island, where the historic Garrison horse racing takes place year-round.
If you’re looking to soak up some winter sun by a pool lounger and nothing more, then any island in the Caribbean will do—the hotels in St. Barts are amongst some of the best in the world. But if you’re willing to dig a little deeper and venture beyond the resort gates, these are the best islands in the Caribbean.
What is the best Caribbean island for families?
When little travelers are involved, the ease of a resort jam-packed with activities can take the strain off parents and let everyone enjoy the trip. For this reason, Barbados is the ideal Caribbean island for families, and there’s everything from larger, more affordable resorts to smaller boutique offerings. For intergenerational holidays and trips with slightly older children, consider hiring out a villa—Oliver’s Travels allows customers to filter results by “great for kids.”
When is the best time to travel to the Caribbean?
The Caribbean’s high season runs from mid-December to mid-April, with the winter holidays bringing the biggest crowds and the highest prices. The rainy and hurricane season runs from June through the end of November. You’ll likely find more affordable flight and hotel prices during the shoulder season (May, June, and early December) which makes this time a particularly enticing one to travel to the Caribbean.
What is the prettiest Caribbean island to go to?
We don’t like to pick favorites, especially when beauty is so abundant as it is in the Caribbean. However, if we must, then we’d recommend St. Lucia as the prettiest island in the Caribbean. St Lucia is well known for its stunning Piton mountains, a UNESCO World Heritage Site that offers some of the best views in the Caribbean. The island is green, lush, and blessed with incredible beaches.