Skip to Content

The 5 Caribbean Islands That Rich People Go To

The Caribbean is full of luxurious locales that the wealthy elite love to frequent due to perfect climates, azure ocean views, and secluded tranquility. If you want to travel “rich and famous” adjacent, you’ll need to know where the hotspots are and why they are such a draw to those with deep pockets. Do you want to know where the rich hang out in the Caribbean? 

Caribbean Islands That Rich People Go To 1 1

Table of Contents

What islands do rich people visit in the Caribbean? 

The top five Caribbean islands that rich people love to travel to are: 

  1. St. Maarten
  2. Turks and Caicos
  3. Virgin Gorda, The British Virgin Islands
  4. The Cayman Islands
  5. St. Barts

We’ll break down where to go to live the life of rockstars and tech investors, where to stay when you get there, as well as the best times of the year to visit. 

How did we determine our top five Caribbean destinations beloved by the wealthy? We compiled our list by studying the habits of those with the most disposable income and considering which islands had the most top-end vacation stays, beaches, and experiences. In addition, we took a list at luxury property listings to determine what the rich gravitate towards the Caribbean isles. 

Without further adieu, we present the results. 

The Top Five Caribbean Islands Where Rich People Love To Travel

1. St. Maarten

Caribbean Islands That Rich People Go To 2

St Maarten is the ideal sun-worshiping palm tree-fringed paradise that most people think of when they imagine winning the lottery. Its famed dueling personalities resulting from the island being split into a northern portion that is French and a Southern end that is Dutch give the island of St. Maarten a unique personality. 

St. Maarten is a place for the indulgent traveler that loves the freedom of the topless white sand beaches and non-stop thumping beats of the nightlife, and a class of luxurious seclusion and tranquility that can only be purchased with deep pockets. 

Although it is frequented by the rich and famous, it also has accessible accommodations and experiences, making it a great way to vacation in a luxury destination without breaking the bank. 

Who Goes There

Harry Belafonte is rumored to live on the French side of the island, and Donald Trump also owns property there. St Maarten is also famous for its New Year’s Eve parties and attracts celebrities yearly over the holidays. 

Where To Stay

Rich people who go to St. Maarten usually live or rent private properties around the islands. If they aren’t staying at sprawling beachside villas or a private yacht offshore, than they might be found at five-star Belmond La Samanna or four-star La Plantation

When To Go

The peak season goes from December to April, so if you want to avoid the crowds, it’s best to travel outside this period. One of the most famous events of the rich and famous, the Heineken Regatta, happens each year in March. 

2. Turks and Caicos

Caribbean Islands That Rich People Go To 3

Turks and Caicos are 40 different islands and cays, of which just eight are inhabited and separated into two distinct island groups.

Over the past several decades, Turks and Caicos have evolved past the island off the beaten track to the place with the 1% of wealth flock to for its pristine beaches that have a unique hint of pink and tranquil shorelines. 

The wealthiest elite generally stays in the Grace Bay Beach area, which hosts a seven-mile stretch of perfect white sand beach. In addition, Long Bay in Providenciales hosts many ultra-luxurious mansions.

The vibe in Turks and Caicos is a more secluded paradise type of luxury over St. Maarten’s over-the-top nightlife version. If St Barts is the place to be seen, then Turks and Caicos is the place to escape. 

Who Goes There

Kieth Richards owns property here and joins Bruce Willis, Oprah, and at one time, Prince. The Kardashians also frequent beachfront property in Providenciales. 

Where To Stay

Amanyara is the ultimate luxury resort in Turks and Caicos with five-star service. In addition, many celebrities have Beach Enclave’s North Shore property with nightly rates starting at a cool $3700. 

When To Go

The good news about Turks and Caicos is that its location enjoys year-round sunshine with astonishingly low rainfall compared to other Caribbean islands. April through June see slightly lower temperatures which might appeal to those who want more temperate weather. 

3. Virgin Gorda, The British Virgin Islands

Caribbean Islands That Rich People Go To 4

Virgin Gorda has long hosted a myriad of the rich and famous. It is one of the four British Virgin Islands, including Jost Van Dyke, Tortola, and Anegada. Of the four, Virgin Gorda is home to the most luxurious properties and waterfronts. 

However, it is best known for its rocky labyrinth of boulders known as The Baths, world-class snorkeling and scuba diving, and beautiful hiking trails. 

The British Virgin Islands has quickly gained traction as a playground for the rich and famous with private island retreats and plenty of space for luxurious super yachts with private chefs and the best water toys a millionaire can buy. 

Who Goes There

Sir Richard Branson has multiple property investments in the area as well as Google’s Larry Page. 

Where To Stay

Oil Nut Bay is located off the Eastern Tip of Virgin Gorda and is the ultimate in rich, opulent luxury. It is a fully sustainable resort with just 11 luxury villas complete with butler service, private pools, and a secluded shoreline. 

When To Go

The British Virgin Islands are in the hurricane belt of the Caribbean, in order to avoid this wet season, aim to go between December and May. 

4. The Cayman Islands

Caribbean Islands That Rich People Go To 5

The Cayman Islands comprises Grand Cayman, Little Cayman, and Cayman Brac and is located just south of Cuba. It hosts the super yachting life of the rich and famous as well as spectacular conditions for scuba diving, water sports, and sportfishing. The rich love the laid-back cruising life, picture-perfect villa accommodations, and luxury fine dining opportunities. 

Ultra-high net worth individuals are attracted by thriving financial and investment sectors due to their tax-neutral status. It is also a premium locale that can be reached in just 70  minutes from Miami. 

Who Goes There

Tom Cruise, Arnold Schwarzenegger, and Al Pacino have all been known to spend time on the Cayman Islands. 

Where To Stay

The wealthiest neighborhood in the Cayman Islands is located on Grand Cayman along Seven Mile Beach, where property prices can reach $1300 per square foot, which is the case for the Watercolors Residences. 

When To Go

January and February are the coolest months of the year to visit and have the least chance of rain. March through June are off-season times and generally quieter with fewer tourists and empty beaches. 

5. St. Barts

Caribbean Islands That Rich People Go To 6

St Barts is a french speaking Caribbean Island famous as the ultimate luxe escape for the wealthy. It is flush with luxury yachts, high-end dining, and designer shopping. A-listers flock to this idyllic locale for a large part due to its low-key culture that typically respects people’s privacy and space. 

In addition, St. Barts is known as the Caribbean’s Shopping Capitol, with designer brands lining the waterfront. 

The marina in the island’s capital, Gustavia, is a hotspot to anchor the world’s most opulent super yachts, where the surrounding waters are known to have some of the best sailing on earth. If boats are not your thing, St Barts offers 22 of the most pristine, white sand, sparkling blue beaches that the Caribbean has to offer. 

Who Goes There

Jeff Bezos has been known to anchor his super yacht to go into St Bart’s for the day, while Beyonce, Mike Tyson, and Dua Lipa have also been recently spotted there. Russian billionaire and soccer team owner Roman Abramovich also owns property on the island. 

Where To Stay

Known as the wealthiest elite getaway, Cheval Blanc is the premier place to stay on St Barts. It features intimate accommodations, five-star dining, and access to one of the island’s best private beaches. 

When To Go

Late November to January are peak party and party goer season. If the nightlife is your favorite place to splash your cash, this would be the ultimate Caribbean nightlife for the rich and famous. 

If luxury means peace and quiet and secluded villa life, then the off-season from February to May is a perfect time to visit, while June to November is hurricane season and should be avoided.