School is back in session and the days are already becoming shorter. The weather is getting crisp and the cold front is on the way. Fall is upon us — and that’s great for travelers to the Caribbean, because it’s the season with some of the best bargains of the year — and some of the smallest crowds. Right now is the perfect time for a getaway, whether you’re seeking an adventurous long retreat or a beachy extended weekend. Here are the best Caribbean islands to visit this fall.
The re-branded Four Seasons in Anguilla.
Anguilla
The Caribbean’s beach capital is beautiful all year round, but it’s getting a boost in October with the re-branded Four Seasons Anguilla (the former Viceroy), which is now taking bookings for travel beginning Oct. 20 and offering perks like a free extra night. Another option is the luxe boutique Frangipani, which just debuted a new beach villa.
Tropic of Cancer Beach
Little Exuma
Connected by a small bridge to its sister island of Great Exuma, this is the island of dreams: no high-rises, no crowds, no problem. It’s a tiny oasis of beach-filled dreams and more rentable beachfront villas than you can count. Its biggest claim to fame? Tropic of Cancer beach, a wide swath of white sand, where the Tropic of Cancer actually runs right along the sand.
Boucan by Hotel Chocolat in St Lucia
St. Lucia
There are really two St. Lucias: the lush, rainforest-packed south of the island, home to cacao plantations and the famous Pitons, and the more bustling, developed north of the island. So if you want to experience the full beauty of the island, the best bet is a two-hotel combo. There are a host of ways to mix and match, but we like the boutique Boucan by Hotel Chocolat in Soufriere combined with the luxurious Cap Maison on the northern tip of the island.
Grand Turk
While Providenciales is the Turks and Caicos’ tourism capital, there are myriad pleasures awaiting you in the archipelago’s other outposts. So why not take a diving getaway this fall in one of the region’s most underrated adventure destinations, Grand Turk? The island is home to some serious underwater scenery and a distinct lack of crowds. When you’re on land, try a stay at the Bohio Dive Resort.
St. Kitts
While the island’s hotly-anticipated Park Hyatt won’t open until next year, there are some wonderful small properties to explore in tiny St. Kitts, none more charming than the Ottley’s Plantation Inn. This is a classic plantation hotel, and offers an authentic Kittitian experience. The best part? You can save 30 percent on fall stays.
Grand Cayman
It’s easy to get to, luxurious and is blessed with one of the world’s best beaches, Seven Mile Beach. Grand Cayman is one of the Caribbean’s most complete destinations, and that makes it perfect for a fall getaway. For great rates, try the Westin Grand Cayman, set right on the heart of Seven Mile Beach.
Antigua
Fall in Antigua means you get 365 beaches all to yourself, from popular spots like Jolly Beach to less-trafficked strands like Morris Bay. Bu for a truly classic Antiguan experience, head for the Blue Waters resort, the island’s best boutique hotel and a truly timeless property.
Punta Cana
If you’re thinking of an all-inclusive fall trip, it’s time for a visit to Hispaniola and Punta Cana. The Dominican Republic’s tourism hub has a vast array of everything-included properties. For a hip, energetic experience, try Royalton’s CHIC Punta Cana all-inclusive resort.
Aruba
It’s outside of the hurricane belt, meaning weather isn’t a worry here, and when you’re sipping a cocktail on the sand, you’ll be worry free. Your best option? The adults-only Bucuti & Tara Beach Resort, our favorite hotel on the island, situated on the most beautiful stretch of Eagle Beach.
The Bacolet Beach Club
Tobago
Still a very exotic destination for most US travelers, Tobago is full of rustic, castaway-style beaches and a host of charming small hotels. Your best bet right now? The Bacolet Beach Club, an increasingly chic property that’s set on one of the island’s most stunning small beaches.