With over 70,000 individual islands, the Caribbean has so many vacation options. We're here to help.
For many vacationers, the Caribbean islands come to mind when thinking about booking a tropical getaway. But look beyond the fruity tropical cocktails and the sandy white and pink beaches (which, without a doubt, are amazing) to experience the true culture of these charismatic islands, each with a unique personality and background history.
See our list of off-the-radar destinations to visit among the many islands of the Caribbean, providing your fix of adventure (and some downtime, too).
Get to Know the Antigua and Barbuda Twin-Island
Although this Caribbean country is known as the twin-island, its two largest parts (Antigua and Barbuda) are far from the same. Antigua is the larger island and more known by tourists, home to the island’s capital of St. John’s that is filled with marketplaces and monumental structures, like the St. John’s Cathedral Divine. But travel to the southern-most tip of Antigua for The Lookout in Shirley Heights, where spectators can witness a clear view of the entire English Harbour.
Then we have Barbuda, Antigua’s sister island, that embodies a completely different personality. Located 28 miles north, this island is known for its lush marine life, quiet beaches, and all-around peaceful atmosphere. Visitors will have no problem finding space to swim and snorkel, and can visit the Frigate bird sanctuary to learn more about the red-crested birds that populate the area. In addition to its calming nature, Barbuda is home to some of the most luxurious boutique hotels on the island—from Coco Point Lodge to the Lighthouse Bay Resort—that brings relaxation to another level.
Explore the Unknown Parts of Popular Bermuda
Bermuda is a popular stop along many cruise line routes, but an entire vacation on this trendy Caribbean island will reveal attractions well beyond hustling flea markets and hair braiding.
Start with Hamilton, Bermuda’s capital and a major port where tourists tend to flock, and opt out of shopping to learn about its natural surroundings. For the adventurous type, book a tour of Fantasy Cave that involves a challenging climb down the cave, then back up to the top. Or for a more tranquil experience, book an eco tour on Warwick Long Bay (the largest beach in Bermuda) and walk along the pink sands while learning about the island’s history and marine wildlife.
And then there’s St. George, the oldest occupied town in Bermuda dating back to the 17th century. Declared a UNESCO World Heritage site, this town is speckled with historic houses, churches, and forts to explore. Once you've learned enough for one day, we recommend taking a break with an ice cream from the nearby Bailey’s Ice Cream Parlour, serving unique flavors like rum raisin and Dark & Stormy.
Wander the Spanish Town of Remedios, Cuba
Ever since the Cuba ban lifted for Americans, the large Caribbean island has been the center of attention for travelers. Although it’s tempting to go straight for Havana—the capital and largest city in the sovereign state—go a bit off the beaten path and visit the small Spanish colonial town of Remedios.
Remedios is located in the Villa Clara province, where visitors can see original 16-century Spanish architecture. Historic monuments and colonial buildings surround the Plaza Marti, including the Parroquia de San Juan Bautista—a former convent that now runs as a Baroque church—with gold-encrusted altars revealed during renovations. And discover the Cuban replica of Lady Liberty located right next to the plaza park, a monument to the Martyrs of San Juan de los Remedios.
Embrace the Cultural Side of Gustavia, St. Barths
Since the first settlement in the 1600s, Europeans have influenced the culture of St. Barths (or as the French call it, St. Barthélemy) that is seen through colonial styled architecture, authentic cuisine, and buzzing ports. The French West Indies Island gained a fashionable reputation over the years, especially in the capital of Gustavia, where luxury hotels and boutique shops have popped up left and right. Yet the area still takes great pride in its historic sites and cultural celebrations, making a trip to Gustavia much more than a glamorous trip.
Stroll along the harbor to witness wooden and stone buildings dating back to the Swedish era, like Le Brigantin house that was occupied by a wealthy merchant family in the early 19th century. Be sure to pop by the fish market in the morning (even if you don’t intend on buying) where the area is vibrant with fisherman selling their freshly caught fish. And during the springtime, get in the middle of the action at the annual Transat AG2R ocean racing event.
Become Artistc With the Locals in Grenada
Don’t judge this petite island by its size, where a massive energy exists through its passion for the arts. Grenada locals constantly celebrate their love of calypso—Afro-Caribbean music that dates back to the 20th century—especially when a music festival is fast approaching. Spring breakers can take part in the Pure Grenada Music Festival, a weeklong event featuring local musicians across the island. And throughout the island, visitors can learn more about Grenada’s culture through folk tales, dances, and colorful art seen around every corner.