American vacationers have enjoyed a rich romance with the Caribbean for decades. These islands offer staggering diversity, both in their cultures and backgrounds. High-end locations such as St. Barts cater to deep-pocketed, all-inclusive havens such as Jamaica and the Dominican Republic check off the affordability box, while destinations such as Cancun appeal to the party crowd. Easy beach breaks remain popular, but the general trend toward experiential vacations draws people to events such as Antigua Sailing Week and land-based adventures like canyoning, hiking and climbing. It may seem like a daunting task to pick the perfect island, but this guide carefully matches the destination to the holidaymaker: time to make a Caribbean decision.
Best for Rest and Relaxation – Turks & Caicos
Located southeast of the Bahamas, the 40 low-lying islands and cays of the British Overseas Territory of the Turs and Caicos Islands are an excellent option for some R&R. Once the vestige of notorious pirates such as Anne Bonny, these days the shorelines and waterways of these unspoiled islands are patrolled by chilled-out vacationers paddleboards, with leatherback sea turtles and brown pelicans among the wildlife.
Grappling with a bonefish on a sport fishing trip, hunting for birdies on the golf course, or diving the barrier reef of Providenciales is about as lively as it gets. Further aiding the islands’ R&R credentials are the wellness offerings at properties such as Sailrock Resort in South Caicos. Sandy strips such as Grace Bay on Providenciales bring travel brochures to life with palm-lined beaches and calm turquoise waters.
Best for Culture – Puerto Rico
Having been informed by everything from Spanish and Taino to African and U.S. influences, the Puerto Rico of today is a fascinating amalgam, its rich history writ large in its colorful architecture, gastronomy and customs. Tourism is slowly but surely recovering from the devastation of Hurricane Maria in 2017.
From salsa and bomba to plena and reggaeton, music and dancing feature prominently, soundtracking the lively nightlife along the beachfront vacation strips of Condado and Isla Verde in the capital San Juan. It’s San Juan’s beguiling old town, however, with its cobblestone streets, colorful Spanish colonial buildings, and historic fortifications that casts the most powerful spell. The Museo de Arte and the impressive Plaza de Armas, along with all manner of charming boutique hotels.
Old San Juan makes a happy hunting ground for foodies, home to popular spots such as La Bombonera and Marmalade, with organized gastro tours a popular option. Come evening, spots such as Carli’s entice visitors with drinks and live music.
Properties like Embassy Suites by Hilton Dorado Del Mar, to the west of San Juan, make great bases, while to the south of the island, Puerto Rico’s second city, Ponce, makes for a nice contrast to the capital. Trolley tours tick off the sights, including distinctive colonial architecture and Plaza Las Delicias, the Ponce Museum of Art offering added insight. A stroll along Paseo Tablado La Guancha makes a pleasant preamble to dinner at a seafront restaurant such as El Paladar.
Rum distillery tours are another popular activity for tourists wanting to get to grips with this island’s fascinating history. Factor in Puerto Rico’s other attractions – from vacation centers such as Palmas del Mar and Flamenco Beach to bioluminescent bays – and it’s easy to see why Puerto Rico has been dubbed “All Star Island.”
Best for Honeymooners – Nevis
For Old World charm and romance, Nevis is the place. This compact gem is dominated by Nevis Peak, a lofty dormant volcano, covers just 36 square miles and has been luring starry-eyed newlyweds for as long as anyone can remember.
Life moves slowly on Nevis, aided and abetted by beguiling boutique resorts with dreamy suites, centered on old plantation properties. Atmospheric restaurants such as Restaurant 750 at Montpelier Plantation Inn cater to the lovestruck.
Romantic activities for couples range from private sunset horse rides along the beach, offered by the likes of Nevis Equestrian Centre, to watersports at Oualie Beach, where Nevis Yacht Charters offer private tours.
With a lovely choice of characterful venues, from beach spots to quaint local churches and old sugar mills, you may wish to hold your wedding ceremony here, too.
Best for Families – The Bahamas
Aside from being Caribbean’s undisputed cruise capital – many major cruise lines actually have their own private islands in this region – the Bahamas is also a big hit with vacationing families who, upon flying into the bustling capital of Nassau on New Providence, find a lively island awash with family-friendly resorts and attractions.
The biggest of these resorts is Atlantis, which sprawls over New Providence’s satellite island of Paradise. It’s a genuine crowd pleaser with the fun and very popular 141-acre Aquaventure water park, stingray encounter experiences, snorkeling, golf and spas. Fun activities on New Providence itself include exhilarating Bahamas Jet Boat rides and Stuart Cove’s submarine adventure trips.
For a more authentic, less touristy option, consider the Out Islands. Known by the locals as “the Family Islands,” these cruise-free locations, such as Harbour Island, tempt with their laid-back vibe. Excellent properties like Tiamo Resort feature some of the region’s best beaches.
Direct flights link islands such as Cat and Eleuthera to airports such as Fort Lauderdale. Alternatively, enjoy a day trip to the Outs from Nassau and take in the scenic Exuma Cays or snorkel alongside the famous swimming pigs of Pig Beach, along with other colorful locals such as iguanas and stingrays.
Best for Adventure – Belize
Diving the Blue Hole is a bucket list staple for many. Dive trips exploring this eerie subterranean sinkhole combine well with nearby dives such as Half Moon Caye Wall, which offer a great range of marine life.
Back on land, San Ignacio, 72 miles from Belize City, is Belize’s adventure capital. From kayaking the Macal River to hiking jungle paths and swimming at nearby waterfalls —the options are vast.
The nearby Actun Tunichil Muknal caves are now the haunt of thrill-seekers “tubing” the underwater river. Other Mayan sites within easy reach include Xunantunich, Caracol and Cahal Pech, which can be visited on horseback. Equestrian endeavors are also popular on visits to the Mennonite community of Blue Creek in northern Belize, a region which can be explored further on boat trips along the New River.
More adventures await in Cockscomb Basin Wildlife Sanctuary. The jaguar preserve has excellent hiking trails and is the starting point for climbing Belize’s tallest mountain, Victoria Peak.
Best Value – Dominican Republic
Brimming over with pocket-friendly, all-inclusive hotels and expansive beaches, this island attracts everyone from sun-worshippers to watersport-lovers to golfers, drawn to its excellent and affordable courses.
Best for Wildlife – Guyana
The rainforest of Guyana is home to a huge range of wildlife, including jaguar in areas such as Iwokrama Rainforest. Other top spots are Surama Mountain, Kaieteur Falls and the Burro-Burro River.
Best for Hiking – Dominica
Mountains, gorges and spectacular waterfalls — not to mention hot springs and the Boiling Lake in picturesque Morne Trois Pitons National Park — are just some of the attractions found along trails such as the epic 115-mile Waitukubuli National Trail.
Best for Foodies – Grenada
From high-end dining at Rhodes Restaurant and Beach House to learning about food production while touring the Belmont Estate and attending events such as Grenada Chocolate Festival. Granada has much to savor!
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