Caribbean Celebrity Spotting Archives - Caribbean Islands Travel Guide

The Caribbean has long been a preferred escape for celebrities seeking privacy, comfort, and a slower pace of life. With its collection of secluded islands, discreet resorts, and naturally exclusive settings, the region offers an environment where high-profile visitors can relax away from constant public attention.

Celebrity interest in the Caribbean spans both well-known destinations and quieter, low-profile islands. Places such as St. Barths are recognized globally for their glamour, while islands like Mustique and Anguilla attract visitors looking for discretion, space, and understated luxury. Geography also plays a role, with many islands positioned within easy reach of North America while still feeling removed from everyday routines.

In this guide, we explore Caribbean islands commonly associated with celebrity travel, highlighting what draws attention to each destination and why they continue to appeal to some of the world’s most recognizable figures.

Each island offers a different balance of privacy, lifestyle, and cultural character, contributing to its appeal among celebrity travelers.

1. Caribbean Celebrities In St. Barths

One of the most family-friendly locations in the Caribbean, St. Barths attracts many celebrity families, including Martha Stewart’s and Jessica Alba’s, for example. With world-class shopping, and known for its style, sophistication, and exclusivity, St. Barths is the best place in the Caribbean to spot celebrities (and often times their families as well)!

Martha Stewart loves St. Barths and frequently mentions the island and her vacation home there in her interviews. She compliments the dining, shopping, and family-friendliness as making St. Barths her favourite exotic island.

Jessica Alba, husband Cash, and their kids love snorkelling, swimming, and playing on the pristine beaches of St. Barths, spending weeks there on their annual vacations. Most recently, after Chrissy Teigen and John Legend left the island, Rachel Zoe and her family joined in as well to keep Jessica and her family company.

The easiest and most convenient way to get to the small yet beautiful island of St. Barths is by one of our affordable private charter flights from Antigua that we are honoured to be operating regularly.

2. Celebrities In Mustique, Celebrity Spotting.

An unspoiled island paradise, the private island of Mustique offers the ultimate in luxury and privacy. Reaching the island requires a connecting charter flight from Barbados, thus making the small island relaxed and less crowded. Many ultra-famous celebrities are attracted by the seclusion and specialty service, ranging from rock legends to England’s royal family.

Prince William and Kate, along with baby George, recently visited the island to celebrate Kate’s mother’s birthday. They have visited the island in the past as well for romantic getaways, as the island is well known for romance. William’s aunt Princess Margaret owned a vacation home on the island and was formerly a frequent visitor as well.

The Rolling Stones love Mustique for its seclusion and lack of media presence. A welcome escape from the hustle and bustle of the big city, the band even recorded albums on the island. Moreover they aren’t the only music mavens to escape the lime light for some major relaxation; Jay Z has also being known to vacation on the privacy-assured paradise.

3. Celebrities In Anguilla

The most up-and-coming destination, Anguilla is less well known when compared to many of our other celebrity hotspots, but is greatly growing in popularity as of late. Some are even calling it the “New St. Barths,” due to its growth in popularity.

Popular with the likes of Liam Neeson, Ellen DeGeneres, Derek Jeter, 50 Cent, and frequent visitor Michael Jordan, the island is known and loved for its relative lack of box stores. Yet to become crowded, Anguilla retains a sense of charm and natural beauty that attracts celebrities from around the world.

With over 30 beaches, a world class golf course, and amazing dining, Anguilla has it all without losing its natural appeal. The luxurious Viceroy Anguilla is the most popular place to spot celebrities, though recently growing hotel and condo building Zemi may take over in the near future.

While luxury, beauty, and the up and coming edge of the island make it attractive to celebrities, Anguilla is also known for its excitement. One of the best places in the Caribbean to try watersports, celebrities can enjoy sports without being pestered by paparazzi.

Also a small Caribbean island without a big commercial airport, the most convenient and affordable way to get to the island quick, safe and in a fun way is by one of our charter flights to Anguilla.

4. Celebrities In Turks & Caicos

One of the fastest-growing celebrity destinations in the Caribbean, Turks & Caicos has become a favorite for those seeking luxury combined with relaxed island living. Known for its powdery white beaches, crystal-clear waters, and high-end private villas, the islands offer celebrities privacy without sacrificing comfort or style.

Frequent celebrity visitors include Drake, Kylie Jenner, Ben Affleck, Jennifer Lopez, and Bruce Willis. Many are drawn to the calm atmosphere, upscale beach residences, and the ability to enjoy island life without the crowds often found on more commercial Caribbean islands.

Turks & Caicos is especially popular with celebrities traveling in groups or with family, thanks to its spacious villas and low-key social scene. Long beach walks, private boat excursions, and quiet dining experiences are among the most enjoyed activities.

With limited commercial flight options and a strong emphasis on privacy, private charter flights are often the preferred way for celebrities to travel to Turks & Caicos, offering convenience and flexibility when arriving on the islands.

5. Celebrities In Barbados

Barbados has long been associated with celebrity culture, blending Caribbean charm with a well-developed luxury lifestyle. The island offers a mix of vibrant culture, world-class dining, and some of the Caribbean’s most refined beachfront properties, making it a long-standing favorite among high-profile visitors.

International celebrities such as Simon Cowell, Tiger Woods, and various fashion and entertainment figures are known to vacation regularly in Barbados. The island is also famously home to global music icon Rihanna, further strengthening its celebrity appeal.

Celebrities visiting Barbados enjoy the island’s balance between social energy and privacy. Whether attending exclusive events, enjoying beachfront dining, or retreating to private villas along the west coast, the island caters comfortably to both public and low-profile lifestyles.

With its established luxury infrastructure and excellent regional connections, Barbados is frequently accessed by private charter flights, allowing celebrities to travel discreetly while enjoying seamless access to the island.

6. Celebrities In St. Lucia

St. Lucia is widely recognized for its dramatic natural beauty and romantic atmosphere, making it a popular choice for celebrities seeking seclusion and scenic surroundings. The island’s lush rainforests, volcanic peaks, and quiet beaches create an ideal environment for private getaways.

Celebrities such as Oprah Winfrey, Beyoncé, Jay-Z, and Brad Pitt have been associated with visits to St. Lucia, often choosing the island for extended stays rather than short social trips. The emphasis here is on relaxation, privacy, and nature rather than nightlife or public appearances.

St. Lucia particularly appeals to celebrity couples and honeymooners, offering an escape that feels remote yet refined. Activities typically include private beach time, sailing, spa retreats, and enjoying panoramic views from secluded hillside accommodations.

Due to its terrain and emphasis on exclusivity, private charter flights are a preferred travel option for celebrities visiting St. Lucia, allowing for direct and comfortable access to the island.