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Caribbean Spotlight: The Best Islands Based on Your Trip Goals

The Caribbean Islands have long been synonymous with exclusivity and luxury, attracting discerning travelers in search of extraordinary experiences. It comes as no surprise that we get a surplus of requests on the best places to stay in the Caribbean each year. With an array of destinations to choose from, it can be a daunting task to choose the perfect island. Whether you seek relaxation, adventure, or the finer luxuries, we will guide you through some of the best Caribbean islands, tailored to different travel aspirations.


Antigua, known as the “land of 365 beaches”, captivates visitors with its abundance of stunning coastal stretches, offering a different beach for every day of the year. But it’s not just the sheer number that sets Antigua apart – these picturesque shores also boast a unique pink hue, thanks to the presence of red shells in the sand grains. As one of the smallest countries in the world, Antigua exudes an intimate and tranquil atmosphere, perfect for travelers seeking a quieter island escape.

Beyond its captivating coastline, Antigua offers a rich heritage and vibrant culture to explore. For nature enthusiasts, lace up your hiking boots and explore the island’s trails, which wind through lush rainforests, revealing breathtaking vistas and hidden treasures along the way.

Pro Tip: Our top recommendation for accommodations in Antigua is Jumby Bay Island. Situated on a 300-acre private island with two white-sand beaches, the resort offers plenty of fun activities, from snorkeling and sailboarding to biking and sunset cocktail cruises. Mind’s made up? Book your stay through our complimentary Hotel Only service.


This tiny, 35-square-mile island is renowned for its spectacular coral reefs and pristine beaches, which hold both ecological significance and breathtaking beauty. You can expect to be greeted with an authentic island vibe as you immerse yourself in the laid-back culture and encounter warm local hospitality.

Anguilla’s charm lies in its commitment to preserving its natural treasures. The island has imposed an embargo on large cruise ships, casinos, and high-rise hotels, ensuring that the beautiful natural landscape remains unspoiled. There are plenty of hidden gems to explore, including tranquil limestone caves and some of the world’s finest beaches.

Please note that because the island is so small, there are limited tours and off-site excursions. Most of the activities found on the island are going to be found at the resort you choose to stay at.

Pro Tip: Our top hotel recommendations in Anguilla are Four Seasons Resort and Residences Anguilla or Cap Juluca, a Belmond HotelContact us to learn more about the distinct differences between the two properties and which hotel is best based on your preferences.

British Virgin Islands

The Virgin Islands are a collection of 112 islands forming the border between the Atlantic Ocean and the Caribbean Sea. Of those 112 islands, 82 belong to the United States and 30 belong to Britain. The British Virgin Islands offers sailing, year-round snorkeling, and beautiful coastlines, making it a haven for yachters and divers.

The British Virgin Islands are more secluded than other islands, so if you’re seeking peaceful seclusion while surrounded by the natural beauty of this tropical paradise, this might be the best destination for you! Whether you choose to relax by the beach or set sail to explore hidden bays, the British Virgin Islands promises a secluded sanctuary.

To learn more, we shared our beginner’s guide to island hopping in the Virgin Islands.

Pro Tip: Our top hotel recommendation in the British Virgin Islands is Rosewood Little Dix Bay. The resort offers 81 contemporary, residential-style rooms, suites, and villas all just steps away from the white sand beach.

Turks & Caicos

Turks & Caicos boasts a collection of exclusive resorts that epitomize refined luxury, however, that’s not all it’s known for. For diving enthusiasts, Turks & Caicos presents a unique opportunity to explore over 1,000 shipwrecks, adding an exciting dimension to underwater adventures. Discover an abundance of wildlife, including the opportunity to go whale watching.

The island’s unique weather patterns contribute to its allure, with an average of only 43 days of rain per year, compared to the Caribbean average of 149 days. Conveniently accessible with 90-minute nonstop flights from Miami, Turks & Caicos is a convenient escape from the States.

Pro Tip: Turks & Caicos is great for families and honeymooners alike and we have had the exclusive privilege of visiting some of the best accommodations the island has to offer. We highly recommend choosing between Wymara Resort & VillasCOMO Parrot Cay, or AmanyaraContact us to learn more about which of these three ultraluxe resorts best suit your needs!

The Bahamas

The Bahamas is a destination that caters to the desires of luxury travelers, offering a combination of ultraluxe experiences, incredible natural landscapes, and a host of activities for all ages. With its fantastic scuba diving and snorkeling opportunities, visitors can explore the underwater world and be greeted by vibrant marine life. This archipelago comprises multiple islands, each with its own distinct charm, providing endless possibilities for island-hopping adventures. Sportfishing enthusiasts can indulge in thrilling expeditions, casting their lines to crystal-clear waters in search of prized catches.

The Bahamas is also famous for its stunning pink sand beaches, creating a beautiful backdrop for strolls along the beach or family pictures. The playful swimming pigs at Exumus have become a very popular attraction over the years if you like to interact with wildlife. The Bahamas is also one of our top recommendations for babymoons!

Pro Tip: Our favorite accommodations in the Bahamas are The Ocean Club, A Four Seasons Resort, BahamasRosewood Baha Mar, or Three Bees Villas, found in our Caribbean Villas blog.

St. Barths

This quaint French-speaking island, formally known as Saint Barthelemy, exudes a laissez-faire attitude, inviting travelers to embrace a sophisticated yet laidback lifestyle. With its calm waters and pristine white sand beaches, St. Barths highly encourages guests to turn vacation mode on upon arrival. The island is home to some of the world’s best luxury resorts and exquisite villas, catering to any luxe budget. St. Barths is one of the few Caribbean islands with gourmet dining experiences and an electric nightlife scene. One of our favorite, quintessential St. Barths experiences is to rent a brightly colored Moke for a day to tool around the island. Beach clubs provide a lively lunch scene and a decidedly European flair that can only be found in St. Barths. For those who love island hopping, St. Barths can easily be paired with the nearby islands of St Maarten or Anguilla!

When it comes to the logistics of getting to St. Barths, leave that to us! Getting to this island is tricky and we have the insider information you need to make your travel experience as seamless as possible.

Learn more about St. Barths in our destination spotlight.

Pro Tip: There are some beautiful choices for where to stay in St Barths. Our top recommendations are Cheval BlancEden Rock, or Villa Rockstar & Villa Nina, found in our Caribbean Villas blog.

St. Lucia

St. Lucia, a mountainous jewel in the Caribbean, is a nature lover’s paradise. From majestic waterfalls to lush landscapes to volcanoes, the island offers an abundance of hiking trails and is begging to be explored. We recommend hiking up Gros Piton for unfiltered panoramic views. St. Lucia’s beautiful beaches with its mountainous backdrop make the island a popular choice for honeymooners.

Pro Tip: We suggest booking your stay at Sugar Beach, a Viceroy Resort. Once the site of an 18th Century sugar plantation, the resort spans over 100 acres of lushly landscaped grounds that sweep down to the stunning white sand Sugar Beach and the glimmering Caribbean Sea.

Dominican Republic

Travelers are drawn to the Dominican Republic because of its enticing blend of natural beauty, vibrant culture, and diverse experiences. Beyond its white sand beaches and Caribbean jungle, the Dominican Republic also has vibrant city life and charming coastal towns. For wildlife chasers, Humpback whales migrate to Samaná Bay between January and March. The island is very easy to get to, with many nonstop flight options to depart from in the States.

Pro Tip: The best places to stay in the Dominican Republic are Amanera and Casa de Campo Resort & Villas. While these resorts couldn’t be more opposite from each other, both have plenty of perks. Nestled within more than 2,170 acres of pristine Caribbean jungle, Amanera overlooks the ocean and provides a Bali-style escape. Amanera is our top choice for a quiet, spacious, relaxed stay. Casa de Campo Resort & Villas is one of the top-rated family-friendly resorts. There are too many activities to name, but we can promise that you and your kids will never be bored here! Casa de Campo is our team favorite for travelers who look for a packed itinerary full of activities on their vacations.

Puerto Rico

Located in the heart of the Caribbean, Puerto Rico offers a perfect blend of rich history, captivating culture, and beautiful, diverse landscapes. Explore the vibrant streets of Old San Juan, where colorful colonial buildings and cobblestone streets tell stories of the past. Unwind at the shores of Flamenco Beach in Culebra, or hike through El Yunque National Forest, a lush rainforest teeming with waterfalls and exotic wildlife. Puerto Rico is also on our list of best places to visit with an expired passport!

Dorado Beach, located on the northern coast of Puerto Rico, is renowned as a top luxury travel destination. It offers pristine beaches, world-class golf courses, gourmet fine dining, and lush tropical landscapes.

Pro Tip: In terms of luxury travel in Puerto Rico, Dorado Beach, a Ritz-Carlton Reserve is by far our top recommendation! Ritz-Carlton Reserve currently boasts only five extraordinary locations around the world. Among these, Dorado Beach in Puerto Rico stands out as a 114-room Ritz-Carlton Reserve property, steeped in history and regarded as one of the Caribbean’s most coveted destinations since its opening in the 1950s.


Travelers love this idyllic Caribbean island because of its blend of natural wonders and leisurely pursuits. Nevis is not only a haven for gorgeous beaches and turquoise waters, but also a golfer’s paradise with its renowned Four Seasons Nevis 18-hole golf course. As you tee off amidst breathtaking views, you may even get your ball stolen by mischievous monkeys perched up in the trees above. The resort also offers the chance to hit eco-friendly biodegradable golf balls onto a floating green in the ocean. Beyond the fairways, Nevis is a treasure trove of marine life, inviting snorkelers and divers to explore its colorful coral reefs and if you’re lucky, swim alongside a sea turtle.

Pro Tip: We love sending clients to Four Seasons Nevis. To get the most out of the island, we recommend a 5-6 night stay. This will be enough to enjoy the dormant volcano views, great food, a dreamy town, and a five-star guest experience at the Four Seasons resort.

An Island for Every Traveler

We have a wealth of inventory of places to stay and things to do and while this blog serves as a starting point, ultimately using our Hotel Plus consultative services will help us best tailor your vacation to your preferences. From providing you with consultation resulting in options personalized to your needs to assisting in making arrangements for spa appointments, dining reservations, and transfers, Hotel Plus is designed to elevate the Hotel Only experience.

As a trusted partner, we can give our clients exclusive benefits at any of the hotels and villas recommended in this blog. Most of these benefits include complimentary breakfast, resort credits, room upgrades, VIP status, and more.

Whether you seek the sailing paradise of the British Virgin Islands, a scuba diving adventure to one of 1,000 shipwrecks in Turks & Caicos, or want to tee off at one of the best golf courses in the world in Nevis, the Caribbean islands provide endless opportunities to make unforgettable memories, no matter your trip goals. We can help you select the best Caribbean Island for you based on your preferences. Contact us to learn more or fill out a travel request form to start planning your trip today!

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