Crystal clear water, soft sand, amazing landscapes – the Caribbean islands are some of the most coveted vacation destinations for good reason. But choosing the right Caribbean island for you can make all the difference in terms of having a perfect experience. Whether you’re travelling as a couple or solo, and whether your priority is the beach, romance, shopping, food, water sports, luxury or culture, there’s a Caribbean island that’s perfect for you.
For those Without Passports
US citizens can travel to USVI without a passport. The US Virgin Islands consist of Saint Thomas, Saint John and Saint Croix. Of these, Saint John is my pick for the best Caribbean island if you don’t have a passport. At over 90% national parkland, Saint John is easily accessed by boat or ferry from Charlotte Amelie in nearby Saint Thomas. It is home to some of the top-rated beaches in the world, including the outstanding Trunk Bay, as well as world-class snorkeling at the Virgin Island Coral Reef Monument. Even though you don’t need a passport to access it, Saint John will feel like a literal world away for US travelers.
Destinations
- Saint John
- Saint Thomas
- Saint Croix
Accommodations
For the ultimate in Saint John villa luxury, check out eco Serendib Villa. Acclaimed in publications like the Robb Report and Caribbean Travel & Life Top 30 Villas, eco Serendib Villa is, in a word, breathtaking. The hill top views alone are enough to take your breath away, but when you add the stunning architecture, award-winning service, and immaculate attention to detail in everything from the pool to the appliances to the bedsheets, you have an experience that is unforgettable. Plus, the villa is completely carbon neutral and full of fun surprises like a life-sized chessboard.
For Solo Travelers
If you’re traveling solo, you want somewhere that’s fun, beautiful and affords plenty of opportunity to both meet people and have a great time all alone. The Cayman Islands and St Barts fit the bill perfectly, but my top pick is Barbados. With the beautiful, serene beaches on the Gold Coast, you can completely avoid other travelers and have an amazing time if you so desire. With fantastic nightlife and a vibrant culture, though, it will be easy to make friends whenever you wish as well. Throw in some of the best food and a slew of great activities and you have the recipe for a top-level solo trip.
Destinations
- Barbados
- Cayman Islands
- St Barts
Accommodations
While a whole Barbados villa may be a bit too large for a solo traveler, there are plenty of 1 bedroom vacation rentals that will be absolutely perfect if you’re traveling alone. Reed’s House Penthouse in Reeds Bay is a perfect example. Overlooking beautiful Reeds Bay, it has its own roof deck, is fully equipped, and is decked out in Caribbean art. The location is also perfect for a solo traveler, as it’s right on the beach and between bustling Holetown, with its fantastic restaurants and nightlife, and historic Speighstown, with its art galleries and cultural and historic sites.
For Romance
While all Caribbean islands have high romantic potential, some stand out all the more, be it due to their natural beauty, exclusivity, or charm. St. Bart’s is my top pick for couples for all three reasons. It has that certain je ne sais quoi in spades, thanks to its old-world architecture, world-class dining, and lush, pristine landscapes. It offers that perfect honeymoon feeling every time, and even if you’re travelling with another couple, or with kids, the villas are often specifically designed to have the bedrooms as far apart as possible to ensure privacy and romance.
Destinations
- St. Barts
- Jamaica
- St. Lucia
Accommodations
One of the most romantic things about St. Barts are the gorgeous 1-bedroom villas with private beach access that are available. Bel’amour in Pointe Milou is a perfect example. It has all the little touches that make for an unforgettable romantic holiday. It’s perched atop a high cliff, offering unforgettable views, while a stunning mural, The Miracle of Love by Jean-Charles de Castelbajac, adorns the livng room. The bedroom design also evokes the feeling of being in a yacht cabin, but with way more space and elegance, as well as Balinese accents. Every other detail, from the fabrics to the tableware, is similarly chosen for its seductive elegance. It’s these touches that separate St Barts villas from the rest and make the stay so romantic.
For Family Vacations
Families are diverse, so ideal destinations are ones that offer a wide range of activities for all different age groups, as well as a high level of service, safety and amenities. My top picks here shine in all three, but I have to give a slight edge to the Dominican. Resorts like Punta Cana and Cap Cana are geared towards families and have everything you need to make for an easy, yet unforgettable, Caribbean holiday.
Destinations
- Dominican Republic
- Jamaica
- Aruba
Accommodations
It’s hard to imagine a more family-friendly Dominican villa than The Pineapple in the Nickelodeon Resort. Inspired by the SpongeBob SquarePants’ very home, this villa has a ton of features that would be right at home in Bikini Bottom and will absolutely delight both the young and the young at heart. That said, there are also plenty of luxurious details for parents and the whole family to enjoy as well, and as the Nickelodeon Resort’s signature villa, it’s one stay that the kids will never forget. 
For a slightly more mature experience, consider the Juanillo 2 at the Cap Cana Resort. Featured in magazines like Elle Decor and Architectural Digest of Germany, it sits on an idyllic stretch of beach and is replete with serene details like hammocks all throughout, a superb infinity pool, and five-star service from its experienced staff.
For Beach Lovers
The Caribbean Islands are, of course, known for their fantastic beaches. Choosing among this list should really be seen, then, as choosing from among the best of the best. By that standard, Turks & Caicos emerges as the ideal destination, with fabulous beaches like Grace Bay Beach and Long Bay Beach that stay pristine thanks to the planet’s third-largest coral reef system.
Destinations
- Turks & Caicos
- Barbados
- Aruba
Accommodation
As the name implies, Seaclusion on beautiful Grace Bay is a stunning oceanfront Turks villa that allows visitors to enjoy their own private slice of one of the best beaches in the world. The stunning modern architecture and luxury amenities like private gym, theatre room, pool room, infinity pool and more make the stay all the more amazing.
For History Buffs
From pre-colonial to colonial to the modern day, the Caribbean islands are home to a diverse, and rich history. While each island has its own unique history to explore, St Kitts & Nevis are real standouts. The Brimstone Hill Fortress in St Kitts dates back to 1690 and is now a national park, and the island also has a scenic railway adapted from the 1630s Wingfield Estate. Historic Charlestown in Nevis, meanwhile, is considered one of the most beautiful Caribbean capitals, and features historic sites, Georgian architecture and the Alexander Hamilton Museum.
Destinations
- St. Kitts & Nevis
- Jamaica
- Saint Martin
Accommodations
Vista de Nevis is a cultural experience all its own. It features classic Caribbean styling, as well as Caribbean art and island artifacts all throughout the villa. This is paired with luxurious detailing and state-of-the-art amenities that round out the experience. And with ocean views on one end and a picturesque view of Mount Nevis on the other, guests are surrounded by the greatest work of art on the whole island – the stunning landscapes.
For Caribbean Culture
Caribbean culture is fresh, vibrant and fun. There’s perhaps no better place to explore and really feel that culture than Jamaica. From reggae to dancehall, Jamaica is the musical capital of the Caribbean, while local artisans can be found all throughout the island. The best part of Jamaican culture, though, are the people – despite how beautiful the island is, it’s always the people that standout as the most memorable part of any trip to Jamaica.
Destinations
- Jamaica
- Barbados
- Saint Martin
Accommodations
Haystack is a bright, airy three-tiered Jamaican villa that features beautiful art pieces from internationally-acclaimed artists all throughout. It also has wonderful touches like a waterfall at the entrance, immaculately-selected designer furniture, a fully-equipped gym and games rom, and a truly magnificent veranda and pool deck. The staff also offers some of the highest levels of professionalism you’re likely to see anywhere.
For Shopping
From souvenir Knick knacks to duty-free luxury goods, the Caribbean islands have a ton of excellent shopping opportunities. Saint Martin stands out, though, thanks to its sheer variety. The Dutch side is known for having the best deals in the Caribbean for things like designer clothes, watches, clothes, perfume and jewellery, with prices up to 40% lower than in the US thanks to the duty-free savings. The French side, meanwhile, is known for French goods such as handbags, perfumes and fashion from French designers. Together this makes for an unbeatable shopping experience in the Caribbean.
Destinations
- Saint Martin
- Saint Thomas
- Dominican Republic
Accommodations
Villa Amalia by Guana Bay Beach is a great spot to take advantage of Saint Martin’s shopping, as well as everything else the island has to offer. Perched atop a cliff with stunning ocean views, the villa also features wonderful amenities like a fully-equipped gym, spa, movie theatre, and games room. The staff is also renowned for their attention to detail and high level of service. A wonderful pick for groups especially.
For Gourmets
The Caribbean islands have their own unique flavor and fare. Once again, though, the top standout here is Saint Martin. While the Dutch side may have the better shopping, it’s the French side that makes its food stand out so much. Mixing fresh Caribbean influences and ingredients, especially seafood, with French technique and culinary expertise results in some of the best dining experiences in the whole of the Caribbean. From restaurants to private villa chefs, Saint Martin is known as the foodie capital of the Caribbean for good reason.
Destinations
Avanti is a perfect representation of the style Saint Martin villas are known for. With a 180-degree view of Saba beach, the terrace area is a work of art, with an L-shaped saltwater pool running along its length that features seating and a table, as well as a leaf-ceiling panel gazebo complete with wet bar and a gorgeous island day bed topping it all off. The interior also features immaculate details, including African-themed décor, designer furniture and the highest-end amenities.
For Relaxation
For many, relaxation is the number one reason to visit the Caribbean islands. But depending on crowds, size and exclusivity, some destinations can certainly be more relaxing than others. BVI stands out in this regard thanks to its low-key atmosphere and stunning sites like the Baths in Virgin Gorda, where you can swim, snorkel or just unwind along a beautiful and serene set of ocean pools and caves.
Destinations
- BVI
- Turks and Caicos
- Jamaica
Accommodations
Baraka Point on Virign Gorda really offers the ultimate in relaxation potential, regardless of group size. It features two acres of tropical gardens, copper peaked pavilions, spacious living, dining and entertainment areas, a spa room and a games room, an infinity pool with panoramic views, and a seaside deck that offers guests the chance to enjoy sunsets in a way they will never forget. If chilling out is an art (and I believe it is), then Baraka Point is a masterpiece among BVI villas.
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For Nightlife
While some of the more low-key Caribbean islands offer very little in the way of nightlife, others feature casinos, nightclubs, bars and more. Once again, Saint Martin comes out as a winner thanks to its sheer variety. From the casinos and massive indoor/outdoor clubs on the Dutch side, to the swanky bars and restaurants on the French side, there’s really something for everyone to enjoy, at all hours.
Destinations
- Saint Martin
- Dominican Republic
- Aruba
Accommodation
Emvie in Orient Bay is perfectly located to take advantage of the nightlife on both the French and Dutch side of Saint Martin. It’s ultra-modern and sleek design, as well as its chic interior and stylish art, is also sure to keep guests in the mood to party, while still offering a beautiful oasis to retreat to at the end of the night.
For Water Sports
Choosing the best Caribbean Island for watersports really depends on the sport. While the scuba diving and snorkelling in Curacao can’t be matched, Jamaica offers world-renowned sailing. With its plethora of deserted cays and islands, though, the Bahamas stands out for any kind of motorized water sports, including wakeboarding, waterskiing, and boating.
Destinations
- Bahamas (motorized)
- Curacao (diving and snorkeling)
- Jamaica (sailing)
Accommodations
Sweetwater in Fowl Cay offers a perfect spot to explore the 365 cays and islands in the Exumas. This is especially so considering that the Bahamas villa comes with its very own 18ft power boat (with unlimited gas). Sweetwater is also directly on your own private beach, and is nearby to the South beach where you can take out a Zuma boat or Kayak for an unmatched workout.
For Ultimate Luxury
In many ways, luxury can be subjective. For me, the ultimate luxury comes down to service, amenities, exclusivity, and privacy, and on that front nothing can beat Jumby Island in Antigua. This pristine, private island can only be reached by boat, with no cars in sight. The villas within offer the highest level of service possible, including nice touches like beach butlers. And the spa, restaurants and surroundings are all arranged to the highest standards possible. It’s quite literally a private island devoted to the ultimate in luxury.
Destinations
- Antigua
- St. Barts
- Jamaica
Accommodation
Spread out over 3.2 acres, Delphis offers the ultimate in luxury with 500m of private coastline, beach gym, mangrove boardwalk, two infinity pools, and multiple private beaches. Luxurious touches adorn every corner of this sprawling Antigua villa estate, and it truly offers the finest in privacy, exclusivity, and service.
Book with a Concierge from Rental Escapes
While choosing the right Caribbean island for you is a good start to personalizing your vacation, it’s only the first step. Your Rental Escapes concierge can personalize your trip down to the finest detail, regardless of which island you choose. This includes everything from making sure your villa is stocked with your favorite foods and drinks to organizing activities and excursions, as well as any special requests. Contact us today to find out how you can make your next Caribbean vacation entirely your own.
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