🏝️ Caribbean Islands Ranked by Exclusivity
A Jet Set Journal Guide to the Most Luxurious Corners of Paradise
The Caribbean has long been the playground of jet setters, royals, and romantics chasing turquoise horizons. But while nearly every island offers sun, sea, and sand, true exclusivity—the kind that whispers rather than shouts—can be surprisingly hard to find.
If you crave privacy over party crowds, Michelin-star dining instead of buffet lines, and infinity pools where the only sound is the sea breeze, this guide is for you.
Welcome to The Jet Set Journal’s definitive list of Caribbean islands ranked by exclusivity—where barefoot luxury, impeccable service, and serenity reign supreme.
🌴 1. St. Barthélemy (St. Barts) – The French Riviera of the Caribbean
Vibe: Chic, sophisticated, and unapologetically glamorous.
St. Barts consistently tops every list of elite Caribbean escapes. A favorite of celebrities and CEOs, this French-speaking gem combines European refinement with tropical charm.
Why It’s Exclusive:
- Strict building codes prevent overdevelopment.
- Boutique hotels like Eden Rock – St Barths and Cheval Blanc deliver Michelin-level service.
- Private villas outnumber resorts, ensuring seclusion.
- Designer boutiques line Gustavia’s harbor—think Dior, Hermès, and Cartier.
How to Get There:
Fly into St. Maarten, then board a short (and scenic) puddle-jumper on one of the world’s shortest runways—reserved for the bold and the beautiful.
💎 Jet Set Tip: Visit during late April or early May to avoid the winter crowds while still enjoying peak weather and access to the island’s chic beach clubs.
🌊 2. Mustique – Private Island Perfection
Vibe: Old-world luxury, privacy, and discretion.
Mustique isn’t just exclusive—it’s practically legendary. Once a secret retreat for British royalty, this private island in the Grenadines remains an invitation-only paradise of villas, hillsides, and beaches.
Why It’s Exclusive:
- Privately owned and home to only about 100 luxury villas.
- Every guest must be approved by the Mustique Company.
- No cruise ships, no public access, no paparazzi.
The Cotton House Hotel, the island’s only formal resort, defines laid-back elegance with oceanfront suites, bespoke dining, and candlelit beach dinners.
💎 Jet Set Tip: Stay in a private villa with a dedicated butler and chef—guests often mingle at Basil’s Bar, the island’s understated social hub.
🌺 3. Anguilla – The Underrated Hideaway for Discerning Travelers
Vibe: Quiet, modern, minimalist chic.
Anguilla often flies under the radar—but that’s precisely why the elite love it. With 33 pristine beaches and no high-rises, it offers privacy without pretension.
Why It’s Exclusive:
- Strict regulations prevent cruise ports and casinos.
- Only a handful of five-star resorts: Belmond Cap Juluca, Four Seasons Anguilla, Zemi Beach House.
- Exceptional culinary scene—think beachfront fine dining at Blanchards or Veya.
Getting There:
No direct international flights keep crowds away. Most guests arrive via private charter or 25-minute boat ride from St. Maarten.
💎 Jet Set Tip: Book a sunset dinner at Sunset Lounge—often considered one of the Caribbean’s most stylish cocktail spots.
🌿 4. Turks & Caicos – Refined Luxury Meets Caribbean Calm
Vibe: Polished, pristine, and perfect for refined relaxation.
Turks & Caicos offers an elegant mix of luxury resorts, powder-white beaches, and turquoise lagoons ideal for snorkeling or yachting.
Why It’s Exclusive:
- Grace Bay Beach is consistently ranked among the world’s best.
- Limited development beyond Providenciales keeps things tranquil.
- Upscale resorts like Amanyara, The Palms, and Grace Bay Club focus on high-touch hospitality.
Best For:
Luxury travelers who want exclusivity without isolation—where private jet arrivals mingle with low-key elegance.
💎 Jet Set Tip: Charter a catamaran for a private picnic on Half Moon Bay, where the only other residents are iguanas.
🐚 5. The British Virgin Islands – Barefoot Luxury for Sailors and Sophisticates
Vibe: Nautical elegance with a touch of adventure.
A favorite of the yachting elite, the BVI offers an intoxicating blend of exclusivity and natural beauty. Each island feels like a private paradise.
Why It’s Exclusive:
- Boutique resorts like Oil Nut Bay and Rosewood Little Dix Bay epitomize Caribbean sophistication.
- The best experiences are reached by yacht—whether owned, chartered, or crewed.
- Even in high season, you’ll rarely see crowds.
💎 Jet Set Tip: Combine your stay with a private yacht charter. Sail between Virgin Gorda, Anegada, and Jost Van Dyke for the ultimate island-hopping escape.
🌅 6. St. Lucia – The Romantic Escape with Natural Grandeur
Vibe: Exotic, dramatic, and impossibly romantic.
St. Lucia’s twin Pitons, volcanic beaches, and luxury eco-resorts make it a favorite among honeymooners and wellness travelers alike.
Why It’s Exclusive:
- Resorts like Jade Mountain and Sugar Beach A Viceroy Resort blend nature with ultra-luxury.
- Each suite (or “sanctuary”) often includes private infinity pools and personal butlers.
- Limited flight routes mean fewer tourists.
💎 Jet Set Tip: Book a helicopter transfer from the airport to your resort for breathtaking aerial views—and to skip the winding mountain roads.
🌴 7. The Bahamas’ Out Islands – Luxury Without Crowds
Vibe: Barefoot chic and blissfully unspoiled.
While Nassau and Paradise Island attract cruise traffic, the Out Islands (Exumas, Eleuthera, Harbour Island) are another world entirely—tranquil, stylish, and favored by yacht owners and A-list retreat seekers.
Why They’re Exclusive:
- Ultra-private resorts like Kamalame Cay, The Ocean Club Four Seasons, and The Other Side Eleuthera.
- World-class diving, pink-sand beaches, and private cays.
- Easy access from Florida via private jet or chartered seaplane.
💎 Jet Set Tip: Visit Harbour Island’s famous Pink Sands Beach—best experienced at sunrise with a mimosa in hand.
🌸 8. Nevis – Old-World Caribbean Elegance
Vibe: Graceful, historic, and discreet.
Often overshadowed by its larger sister island, St. Kitts, Nevis is where time slows and luxury is woven into every quiet detail.
Why It’s Exclusive:
- Limited development ensures tranquility.
- Four Seasons Nevis offers barefoot luxury with golf, spa, and beachfront villas.
- The island attracts privacy-seeking travelers, not crowds.
💎 Jet Set Tip: For a touch of local flair, enjoy a sunset cocktail at Bananas Bistro or a private dinner on Pinney’s Beach.
🌺 9. The Grenadines – Secret Gem of the Southern Caribbean
Vibe: Remote, natural, and effortlessly authentic.
The Grenadines remain one of the least commercialized chains in the Caribbean, beloved by sailors and those seeking untouched beauty.
Why It’s Exclusive:
- Remote access keeps mass tourism at bay.
- Petit St. Vincent and Palm Island Resort redefine barefoot luxury with privacy, personalized service, and zero crowds.
- You can hop by yacht between 32 tiny islands, many completely deserted.
💎 Jet Set Tip: Book a stay at Canouan Island’s Mandarin Oriental—one of the Caribbean’s most exclusive addresses, complete with its own private jet strip.
🌞 10. Barbados – Glamour with Global Appeal
Vibe: Refined, festive, and undeniably elegant.
While Barbados is better known than many on this list, it earns its place thanks to its discreet celebrity scene and sophisticated resort culture.
Why It’s Exclusive:
- Platinum Coast resorts like Sandy Lane and The Fairmont Royal Pavilion set the standard for Caribbean glamour.
- Upscale dining and polo matches draw an international elite crowd.
- The island’s charm lies in its balance—refined yet alive.
💎 Jet Set Tip: Visit in May or November to enjoy calm weather and top-tier service before peak season crowds arrive.
🧭 Honorable Mentions
- Cayman Brac & Little Cayman: Remote yet refined—ideal for divers.
- Dominica: Eco-luxury growing fast, with Secret Bay leading the way.
- Antigua: 365 beaches and luxury icons like Jumby Bay Island.
✨ The Jet Set Journal’s Exclusivity Ranking (2025 Edition)
| Rank | Island | Exclusivity Level | Signature Luxury Experience |
|---|---|---|---|
| 1 | St. Barts | 🌟🌟🌟🌟🌟 | Designer boutiques & private villas |
| 2 | Mustique | 🌟🌟🌟🌟🌟 | Private island, royal heritage |
| 3 | Anguilla | 🌟🌟🌟🌟½ | Discreet five-star resorts |
| 4 | Turks & Caicos | 🌟🌟🌟🌟 | Seamless luxury meets convenience |
| 5 | British Virgin Islands | 🌟🌟🌟🌟 | Yacht-based exclusivity |
| 6 | St. Lucia | 🌟🌟🌟🌟 | Romantic eco-luxury |
| 7 | Bahamas Out Islands | 🌟🌟🌟½ | Barefoot privacy |
| 8 | Nevis | 🌟🌟🌟½ | Classic Caribbean charm |
| 9 | The Grenadines | 🌟🌟🌟½ | Natural seclusion |
| 10 | Barbados | 🌟🌟🌟 | Glamour with culture |
💼 How to Book These Hidden Paradises
To unlock the full luxury experience, book through trusted partners that offer VIP upgrades and exclusive perks:
- Expedia VIP Access – guaranteed late checkout and resort credits.
- Booking.com Genius Level 2+ – hidden discounts on five-star properties.
- Virtuoso Travel Network – private transfer and daily breakfast inclusions.
- Amex Fine Hotels + Resorts – available to Platinum Card® holders.
🌺 The Jet Set Takeaway
Exclusivity in the Caribbean isn’t just about price tags—it’s about privacy, authenticity, and atmosphere.
Whether you’re sipping champagne on St. Barts, anchoring your yacht in the BVI, or unwinding barefoot on Anguilla’s beaches, the essence of true luxury is this:
The fewer people who know your secret escape, the more special it becomes.
So pick your island, pack your linen, and prepare to disappear—beautifully.