Darby's Destinations Luxury Travel - Italy

Which Caribbean island should you visit the first time?

These are the best islands for luxury, food, nature, and family vacations.

September 9, 2022

The Caribbean consists of more than 7,000 islands, islets, and keys. Of course, only a modest proportion of these are inhabited and available for travelers. Choosing which Caribbean island you should visit the first time is a challenge but this guide will help you establish a shortlist.

Saint Lucia

Frequently compared to Hawaii, Saint Lucia is one of the most beautiful Caribbean islands. Two volcanic spires termed the Pitons rise from the island which is blessed with a mixture of black and white sand beaches. Saint Lucia is ideal for travelers seeking excellent hiking opportunities; trails navigate the dense interiors of the rugged isle and lead you to waterfalls. Luxurious properties such as Jade Mountain are ideal for honeymooners and make it easy to recharge with a view over the Pitons. Fun fact: Saint Lucia is the only country in the world to be named after a woman!

Turks and Caicos

​Turks and Caicos is an archipelago of around 40 low-lying coral islets that many say offer the best beaches in the region. While all Caribbean islands provide a luxury experience, Turks and Caicos carries an even more exclusive atmosphere. Oprah Winfrey, Keith Richards, and Rihanna are regular visitors and COMO Parrot Cay does not scrimp on opulence. This is a leading destination for snorkeling, diving, and swimming with sites including a 14-mile-long barrier reef, underwater walls, and wrecks. Caribbean reef sharks, hammerheads, nurse sharks, and bull sharks are frequently encountered on excursions.

Antigua and Barbuda

The remote twin islands of Antigua and Barbuda offer a wonderful combination of beaches, rainforests, watersports, culture, and cuisine. Sailing is the number one pastime in Antigua while golfing is popular. Marina-turned-cultural heritage site in English Harbour, Nelson’s Dockyard is a UNESCO World Heritage Site. Besides the museum that sheds light on Antigua’s marine history, the complex features waterfront restaurants and bars. Antigua is the setting for such high-end properties as the island resort of Jumby Bay on Long Island.

Barbuda provides a more rustic atmosphere with pristine pink beaches, limestone cave systems, and boutique oceanfront accommodations.

The Bahamas

The Bahamas is one of the best Caribbean islands for first-time visitors and is recommended for family travelers. These islands pull together all the key aspects of a Caribbean escape – food, culture, watersports, and sophisticated lodgings. Highlights of the chain include Harbour Island’s Pink Sand Beach and the Bahamian swimming pigs of the Exumas. Scuba divers can plunge into Dean's Blue Hole, one of the deepest marine caverns of its kind. Meanwhile, history buffs can brush up on trivia at the swashbuckling. Pirates of Nassau Museum. As a bonus, the archipelago’s proximity to the US mainland reduces transit time.


Located 18 miles from the ​​Venezuelan mainland, Aruba enjoys a comfortable climate and unparalleled swimming and snorkeling conditions. Flamingoes roam the grounds of the Marriott resort, Renaissance Island. Furthermore, Aruba is one of the best Caribbean islands for foodies. The Kitchen Table is a gourmet extravaganza where Caribbean flavors are fused with Peruvian fine cuisine. Adults-only seafront restaurant Elements specialize in sustainable seafood and locally grown produce with plates guaranteed to appease all diets.

There is so much more to learn about the Caribbean. Contact me and we will design the perfect vacation tailored to suit you.

Ready to embark on your own journey to the extraordinary?