Many people use Jamaica as their entry into the Caribbean, whether its for a food crawl or an exclusive trip to GoldenEye (one of our favorite, small resorts in the world). Even though we might go for different reasons, we all stay for the island's unreal natural beauty. Head to the western town of Negril for some of the best diving and swimming spots in the country (Seven Mile Beach is a particular favorite), then head inland to hike through misty mountains, with guaranteed views of hidden lagoons and waterfalls.
If it's pristine beaches you're after, then look no further: The Cayman Islands—Grand Cayman, Cayman Brac and Little Cayman—have some of the best stretches of sand in the entire Caribbean. Most people head to resorts on Seven Mile Beach (not to be confused with Jamaica's beach of the same name) on Grand Cayman, but head to Owen Island on Little Cayman for a more private beach day. The islands' underwater adventures are just as, if not more, exciting than those on land: Don't you dare leave without visiting Stingray City (off of Grand Cayman) and snorkeling with the surprisingly friendly stingrays.
This British Overseas Territory (just north of the dual-nation island of St. Maarten/St. Martin) is the place to really get away from it all. Your first stop should be Shoal Bay, Anguilla's most famous beach. The blindingly white shore offers soft sand and non-touristy restaurants, plus an offshore reef for snorkelers and divers. For the ultimate luxurious hideaway, book a suite at the newly renovated Belmond Cap Juluca—resort perks aside, the enclave offers unbridled views of Maundays Bay's vanilla sands and blue waters.
From the bright architecture of Old Havana to the beauty of Varadero beach, it's no wonder Cuba has become of one of our favorite destinations in the past few years. The western, inland province of Pinar del Río is a treasure trove of natural wonders, with miles of mountain ranges and tobacco fields (hello, cigars). The region also happens to encompass Viñales Valley, arguably one of the most beautiful spots in the entire country. With its dome-like limestone formations and lush landscapes, the UNESCO World Heritage Site is the perfect place to watch the sun set.
Nearly every hotel along Aruba's leeward beaches is a winner, but it's a waste not to venture off this developed stretch. The island's beaches are some of the best in the entire world, like powder-fine Eagle Beach and unspoiled, undeveloped Arashi. The Arikok National Park, comprising 18% of the island, is a hidden treasure—a cacti-filled landscape well worth exploring.
Rising from the sea like the setting of a King Kong movie, tiny Saba's unspoiled and undeveloped environment makes it memorable. Located in the Lesser Antilles chain just south of St. Maarten/St. Martin, the island's appeal extends both above and below the coastline, from the jagged silhouette of Mt. Scenery (an appropriate name, and the highest point in the Kingdom of the Netherlands) to the diverse and colorful coral reefs. It also happens to have some of the friendliest locals you're likely to encounter.
Virgin Gorda is the third-largest of the British Virgin Islands, with natural beauty covering virtually all of its 8.5 square miles. The island offers quiet beaches and coves and flora-filled national parks. Perhaps the prettiest (and most popular attraction) is the Baths, a seaside area where huge granite boulders form scenic saltwater pools and grottos.
More than a year after the Hurricane Maria made landfall, Puerto Rico has not only recovered: It’s been reborn. Many of the island's hotels used the need to rebuild as an opportunity to undertake indulgent renovations, and a ton of new Airbnbs have popped up across the country. Old San Juan remains one of the best-preserved examples of Spanish Colonial architecture in the Caribbean, with brightly painted buildings and cobblestone streets that could launch a thousand Instagram shots. Meanwhile, hidden gems like the laid-back island of Culebra and Vieques have fantastic snorkeling and never-crowded stretches of sand.
"Drop any preconceptions you might have of what a vacation on St. Barts might mean. It's not all Rolexes or tubs of Iranian caviar for two—it's a naturally gorgeous island with a fascinating history." Indeed, the tony territory has enough scenic views and water sports to give all those five-star hotels a run for their money. On the south coast of the island, Anse de Grande Saline treats visitors to vegetated sand dunes and unobstructed views of turquoise waters. For a more accessible beach experience, head directly to St. Jean, a coastal town that would feel at home along the French Riviera. The calm and clear waters are ideal for surfing, with plenty of boutiques to visit if you need a break from the sun.
The scenery of St. Lucia can be summed up in one jaw-dropping site: a duo of striking spires known as the Pitons. The two volcanic peaks—Gros Piton and Petit Piton—are the most iconic landmarks on the island, and visitors can enjoy them in a variety of ways. An absolute bucket-list experience has to be actually hiking the mountains, an activity which takes the better part of a day. Regardless of which Piton you choose, the climb will be a strenuous and lengthy affair (the hike can take upwards of six hours round-trip—guided tours are essential), but those views from the top easily validate the journey. If you prefer to keep your feet at sea level, plop a towel down at Sugar Beach, set dramatically (and conveniently) between the two Pitons.
Often overlooked, Haiti continues to amaze with its fantastic hiking and dozens of near-empty beaches—not to mention its vibrant modern art scene and cultural events. The entire county is covered with mountains crisscrossed by hiking trails, offering a cool respite from the island's hot and steamy lowlands. Set aside a day to trek up to Citadelle Laferrière (usually referred to simply as "the Citadelle"), an abandoned French fortress near the northern village of Milot. Upon reaching the castle (via horseback ride or a manageable hike) travelers are rewarded with stunning views of the Atlantic Ocean—on clear days, you can even spot Cuba in the distance.
Although Curaçao has often been dwarfed by its sister island Aruba, it has started investing more heavily in tourism—it seems like every day brings about a new hotel or restaurant to the scene. Even without the trendy openings, the 17th-century, UNESCO-protected capital city of Willemstad is as pretty as it is historic. With its pastel-colored Dutch and Portuguese-inspired buildings, the architecture here will impress you from every angle. We'd say the "middle child" of the Dutch ABC Islands is officially ready for its close-up.
The twin-island nation of St. Kitts & Nevis bursts at the seams with charm. But first: St. Kitts. The larger of the two islands is known for its sugarcane fields and well-preserved Brimstone Hill fortresses, best approached on the open-air train that runs along the island's southern coast. For sophisticated lodgings with a view, book a stay at Belle Mont Farm on Kittitian Hill, a 2015 Hot List winner. Situated on the northwestern slopes of Mt. Liamuiga, some of the resort's biggest draws are the private plunge pools and outdoor clawfoot tubs overlooking the sea.
Barbados has something for everyone: pink sand beaches, exotic wildlife (think monkeys, sea turtles, and eight species of bats), and sunsets just begging to be enjoyed with a fresh cocktail. It's no secret that the island also has a global reputation for clubby sports, with private polo clubs and world-class golf courses (including one carved into a limestone quarry) drawing well-heeled groups of repeat visitors—many of them from Britain. For a wilder brand of beauty that doesn't require a membership fee, look to Bathsheba Beach on the east coast. Here you'll find big, surf-able waves and shallow pools carved by the coral reef right off the shore.