The Offseason Guide to the Caribbean

Because you never really wanted to share the beach.

The low season in the Caribbean gives travelers the chance to enjoy a mellower version of paradise than they’d find in winter. Beaches are devoid of Speedo-sporting Europeans and there’s a real opportunity to mix (read: drink) with locals and the die-hard sunseekers. The most important thing? Knowing where to go to keep cool and avoiding the haven’t-showered-for-days budget backpackers.

Stay Longer

From mass resorts in Jamaica to boutique hideaways in Antigua, countless high-end Caribbean hotels are throwing in extra nights for free during the summer to tempt vacationers to stretch their down time. It’s not only a great deal, it’s a great way to get great service. Hotels with rooms to fill are hotels with concierges twiddling their thumbs.

Photo Courtesy of Viceroy Hotels and Resorts

The deals are everywhere. Through Dec. 19, the oceanfront Viceroy Anguillais offering a fifth night free when you book a four-night stay (as well as 50 percent off a second room if you’re traveling with friends). During the last week in August (as well as from Oct 11 – 31) the seriously luxurious, 25-suite Hermitage Bay in Antigua is tossing in two free nights for stays of five or seven-nights.  On St. Barths – always jet set and usually hors de prix – rare summertime savings at tony Hotel Le Toiny entice you for six nights at the price of five. And Summer Sensation, a luxury getaway on overlooked St. Kitts, is willing to hook travelers up with three free nights. Remember: Money saved is money you can spend on drinks.

And don’t forget to forget about hotels. If you can, book a spot at the Nandana Villa on Grand Bahama. With room for 12 guests in an Asian-inspired oceanfront mansion, the villa’s rates plunge from $14,000 per night in winter to a mere $8,500 per night in summer. It’s a fair amount of dough, but not much more than you’d spend in the Hamptons.

Photo Courtesy of St. Kitts Tourism

Get Wet

For surfers, sailors and paddlers of all types, the Caribbean is basically a large blue playground. Come summer, that playground is basically empty and would be amphibious athletes can enjoy the reefs and breaks without having to share. Despite the arrival of the stylish W Resort & Spaon Vieques a few years back (which is offering 30 percent savings on off-season stays, by the way), the former Army base miles off Puerto Rico remains relatively undiscovered by the masses – all the more so during the quieter summer months, when the famed Bioluminescent Bay empties out. Puerto Rico’s high season for big wave surf is winter time, but you can still find waves during the summer at famed spots like Tres Palmas and Wilderness on the island’s rugged northwest corner.

Photo Courtesy of W Retreat and Spa

Summertime also provides serious divers with the opportunity to enjoy some of the region’s flourishing ecosystems without clanging around the back of a busy boat. Check out La Pura Vista’s seven-night Dive, Drive & Dine special, which includes a rental car, daily breakfast, unlimited shore diving and accommodation from just $999 per person, or head to Sorobon Beach Resorton Bonaire for a seven-night Stand Up Paddleboard package that includes your SUP, room and a rental pickup truck for exploring the island.

More of a sailor? Book your adventure in the U.S. or British Virgin Islands through The Moorings by July 28 (for trips through Sept. 30) and get summertime savings of 20 percent off the perfect bareboat catamaran or monohull for your island hopping adventure. Again, money saved is rum in the galley.

Photo Courtesy of Nandana Villa

Monopolize the Beach

Nothing ruins the joy of a beach day like having to fight for towel space. Enter summer, however, and exit the bulk of the scene stealers. Take, for example, Cabbage Beach on Paradise Island in Nassau. Just a few steps away from the sprawling Atlantis resort, it’s the island’s finest beach and – in January – its most crowded.  In August, all you have to do is stroll ten-minutes away from Atlantis’ oceanfront stretch of sand and you’ll be largely alone.

Reggae Beach in St. Kitts, a crescent sweep of sand with a view of Nevis’s volcanic peak, tops the list of normally-crowded beaches you can hog in summer. The other ones: Maracas Bay in Trinidad, Meads Bay in Anguilla, and the famous Pink Sands Beach on Harbour Island in the Bahamas, where the bar gets crowded with tanned-to-the-bones local women. The drinks are cold; the water and the natives aren’t.

Photos by Curtain Bluff Resort