An “if you know, you know” atmosphere pervades Anguilla, a British Overseas Territory in the Leeward Islands. Frequent return visitors and long-term residents praise its crystalline turquoise waters, high standard of living and warm friendliness — in many places on the island everyone seems to know everyone. Compact at just 16 miles long by 3 miles wide, Anguilla is easy to explore, and its close proximity to Sint Maarten/Saint Martin, reachable by a short ferry ride, makes combining destinations simple. Shoal Bay on the northeast coast regularly ranks among the Caribbean’s best beaches, while Meads Bay is bookended by the Four Seasons resort — a prime spot for sunset cocktails — and Malliouhana Resort, the island’s first hotel. Between these lie popular local favorites such as the ever-busy Blanchards Beach Shack. For a quintessential Anguillian afternoon, take a speedboat from Sandy Ground Wharf to tiny Sandy Island to sunbathe, snorkel around the 360-degree shoreline and enjoy local lobster or curried coconut shrimp for lunch.
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Located about 37 miles north of Venezuela’s coast, Curaçao forms one of the ABC islands alongside Aruba and Bonaire and sits outside the hurricane belt, ensuring reliably pleasant weather year-round. The island reflects strong Dutch influences from its long association with the Netherlands. Willemstad’s Otrobanda district evokes 17th-century provincial streets, and Dutch culinary traditions appear in local dishes such as deep-fried bitterballen filled with shredded meat and classic apple pie. The colorful row of buildings along Handelskade is a must-photograph, as is standing behind the oversized “DUSHI” letters — a local word in Dutch and Papiamentu meaning “nice.”
Curaçao is often called the “Island of 35 Beaches,” many of which are calm thanks to protective coves or lagoons. Expect to spot sea turtles at Shete Boka, relax under palapa shade at Playa Knip, and mingle with locals over an Amstel Bright at the beach bar on Playa Porto Mari. Don’t miss a tasting and tour at the Chobolobo Distillery to learn how the island’s signature liqueur is crafted in a color that echoes the sea’s electric blue.
Saint Lucia’s dramatic scenery often invites comparisons to Kauai, especially around the iconic Gros Piton and Petit Piton — two verdant volcanic peaks rising roughly 2,500 feet and listed as a UNESCO World Heritage site. Both peaks are climbable; Gros Piton is commonly chosen by visitors and still requires three to six hours for a round-trip hike. Many resorts on Saint Lucia cater to couples and romantic escapes, offering cliffside one-bedroom villas with private plunge pools and intimate settings.
Activities include coastal sightseeing and snorkeling with Sea Spray Cruises in Marigot Bay and exploring Soufrière. For a unique wellness experience, bathe in geothermal mud at the Sulphur Springs as an alternative to a conventional spa treatment. Saint Lucia also supports a vibrant cacao industry: participate in a Tree-to-Bar experience with Project Chocolat, which combines grove tours, tree grafting demonstrations, hands-on chocolate making and a local market lunch. Rum aficionados should visit Saint Lucia Distillers to tour the facility and sample Chairman’s Reserve and other molasses-based rums.
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LODGING
Baoase Luxury Resort
Set on a private cove dotted with tiny islets, cabanas and palm trees, this five-star villa resort blends high-end service with peaceful seclusion. Curated experiences include yacht excursions, spa treatments and private beachfront dinners.
2 Winterswijkstraat, Willemstad, Curaçao $$$$$
Frangipani Beach Resort
This intimate 19-room beachfront property on Meads Bay epitomizes barefoot luxury, offering all-day dining on the sand and attentive, personalized service tailored to guests’ preferences.
Meads Bay, A12640 West End Village, Anguilla
$$$$$
Stonefield Villa Resort
Enjoy views of the Piton Mountains from your private plunge pool at this romantic cliffside resort nestled in the rainforest. The resort features spacious villas, a calming spa and an open-air restaurant that highlights local ingredients.
Stonefield Estate Resort, Soufrière, Saint Lucia $$$$$
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DINING
Rabot Restaurant
Overlooking cacao fields that influence its menu, this restaurant inside Rabot Hotel integrates chocolate’s sweet and savory profiles in dishes such as seared scallops with cacao-citrus sauce and cacao-marinated rib eye with dark chocolate jus.
Rabot Hotel, RWJX+MPW, Rabot Estate Soufrière, Jalousie, Saint Lucia $$$$
Sandbar
Located near Sandy Ground Wharf, this beachside spot offers views of boats returning to port and a menu of Asian-influenced small plates, including lobster cakes with creamy nuoc cham and charred broccoli with chili crunch.
6W25+6R6, Sandy Ground Road, Sandy Ground, Anguilla
$$$
Zest Restaurant & Beach Café
Explore Curaçao’s surprising gin-and-tonic culture with a customizable menu of botanical spirits and mixers, then linger for Caribbean-style tuna or Chateaubriand while dining with your toes in the sand.
Kaya Damasco, Jan Thiel Beach, Willemstad, Curaçao $$$$$
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INFO TO GO
Most visitors bound for Anguilla fly into Sint Maarten’s Princess Juliana International Airport on carriers such as American Airlines, JetBlue and United and then take a short ferry to Blowing Point in Anguilla. American Airlines has also added direct flights from Miami (MIA) to Anguilla (AXA). Curaçao is served by airlines including American Airlines, JetBlue and Air Canada at Curaçao International Airport (CUR), roughly 8 miles from Willemstad. Direct flights to Saint Lucia (UVF) are offered by American Airlines, JetBlue, Delta and United. Note that some remote resorts require lengthy transfers from Hewanorra International Airport via winding roads, which may be a consideration for travelers prone to car sickness.