Find Your Beach: Your Jet-Set Guide to the Caribbean in May

When the calendar flips to May, the Caribbean starts heating up in more ways than one. It's the sweet spot between the spring break rush and summer humidity, offering sun-soaked beaches, vibrant culture, and just the right touch of tranquility. Whether you're jetting off for Memorial Day weekend or planning an extended escape, this guide will walk you through five incredible Caribbean destinations — plus one you can enjoy without even packing your passport.

Providenciales, Turks and Caicos

Turks and Caicos is synonymous with luxury, and Providenciales (or "Provo" as it's affectionately called) delivers a pristine, upscale experience ideal for private jet travelers. As you descend into Providenciales International Airport (PLS), the crystal-clear waters of Grace Bay come into view — a dazzling welcome mat for your tropical escape. Private flyers benefit from FBO services that offer swift customs processing and VIP lounges, making for a seamless transition from sky to sand.

Grace Bay Beach is the crown jewel here, with its powder-white sand and calm, turquoise waters. It's the perfect backdrop for relaxation, snorkeling, or even paddleboarding. But Provo is more than a beach destination. Divers from around the world flock to the island for its coral reefs and underwater cave systems. On land, you'll find gourmet restaurants like Coco Bistro nestled under palm trees, luxury villas with ocean views, and high-end spas specializing in marine-based therapies. If you're planning a low-key but luxe Memorial Day getaway, few destinations deliver with as much elegance and tranquility as Providenciales.

Why Choose Turks and Caicos?

If you're seeking serenity and exclusivity, this is your destination. Providenciales is ideal for travelers who want to truly unplug and indulge in nature and refinement without distraction.

Turks and Caicos Fast Facts:

• Avg. temperature: 84-86°F

• Ideal for: Beach lovers, divers, luxury travelers

• Highlight: Grace Bay Beach, Chalk Sound National Park

• Arrival Airport: Providenciales International Airport (PLS)

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St. Maarten

As your jet touches down at Princess Juliana International Airport (SXM), you'll immediately understand why St. Maarten is famous among aviation enthusiasts — planes make a low descent just above the beach, offering a thrill for passengers and spectators alike. For private jet travelers, the airport's FBOs provide first-class handling, making your arrival efficient and stress-free.

St. Maarten is an island of duality, split between the Dutch and French sides. This cultural blend means you'll dine on French cuisine in Grand Case in the morning and sip cocktails at a Dutch beach bar by evening. In May, the weather is sunny and warm with refreshing breezes — perfect for catamaran cruises, snorkeling trips, or leisurely shopping in Philipsburg.

The island also has a buzzing nightlife scene. Try your luck at the casinos or book a table at a rooftop restaurant overlooking the marina. With fewer crowds in May, you’ll enjoy more personalized service and quiet corners of paradise. For the adventurous and the sophisticated alike, St. Maarten offers a dynamic experience with the polish private travelers expect.

Why Choose St. Maarten?

This is the place for those who want a rich cultural experience paired with exhilarating island energy — perfect for foodies and socialites who love a little action with their paradise.

St. Maarten Fast Facts:

• Avg. temperature: 83-85°F

• Ideal for: Foodies, adventure seekers, nightlife lovers

• Highlight: Maho Beach, Grand Case dining, sailing excursions

• Arrival Airport: Princess Juliana International Airport (SXM)

Nassau, Bahamas

The moment you step off your private jet at Lynden Pindling International Airport (NAS), you're greeted with the island’s warm breezes and colorful Bahamian spirit. As the largest airport in the Bahamas, NAS offers dedicated FBO services that expedite your arrival and ensure privacy. From there, it's a quick ride to Paradise Island or downtown Nassau.

Nassau is a charming blend of British colonial history and modern luxury. In May, you’ll find yourself in the heart of Junkanoo Carnival season. This cultural celebration fills the streets with music, elaborate costumes, and energetic dancing — an unforgettable way to kick off your Caribbean escape.

Beyond the festivals, Nassau offers everything from championship golf courses and high-end boutiques to historical landmarks like the Queen’s Staircase and Fort Fincastle. For those looking to venture beyond the main island, charter a private yacht to the Exumas for a day of snorkeling, sandbars, and swimming pigs. Whether you're staying at The Ocean Club or a private villa on the beach, Nassau delivers upscale island living with ease.

Why Choose Nassau?

If you're drawn to vibrant festivals and the charm of Bahamian culture — and want to be just a short flight from the U.S. mainland — Nassau offers a perfect balance of accessibility and authenticity.

Nassau Fast Facts:

• Avg. temperature: 82-84°F

• Ideal for: Culture lovers, families, island hoppers

• Highlight: Junkanoo Carnival, Atlantis Resort, Exuma excursions

• Arrival Airport: Lynden Pindling International Airport (NAS)

Punta Cana, Dominican Republic

Punta Cana is where the Caribbean’s natural beauty meets high-end indulgence. Flying into Punta Cana International Airport (PUJ) is a breeze for private jet travelers thanks to a dedicated VIP terminal and personalized immigration services. Within minutes, you're whisked away to a five-star resort or private villa.

May offers warm, tropical weather — ideal for taking full advantage of Punta Cana’s expansive beaches, championship golf courses, and award-winning spas. It’s a top destination for all-inclusive luxury, with resorts like Eden Roc Cap Cana and Tortuga Bay offering private pools, beachfront dining, and full butler service. If you're celebrating Memorial Day with family or friends, many properties host special holiday-themed events and beach parties.

Those seeking adventure can explore hidden cenotes, zip-line through lush forests, or sail out to Isla Saona for a postcard-perfect day trip. Punta Cana is a well-rounded escape for those who want sun, sophistication, and a touch of thrill.

Why Choose Punta Cana?

If you're looking for effortless relaxation with a full suite of activities and pampering amenities — all within the safety and ease of a resort bubble — Punta Cana is unbeatable.

Punta Cana Fast Facts:

• Avg. temperature: 85-87°F

• Ideal for: Couples, groups, all-inclusive vacationers

• Highlight: Resort life, cenotes, golf and spa experiences

• Arrival Airport: Punta Cana International Airport (PUJ)

Puerto Rico

One of the biggest perks of choosing Puerto Rico is convenience. U.S. citizens can fly directly into San Juan’s Luis Muñoz Marín International Airport (SJU) without a passport, and private jet passengers benefit from modern FBO services with expedited customs. In under four hours from most East Coast cities, you're immersed in a Caribbean paradise — no international documentation required.

Puerto Rico is rich with culture and natural beauty. In Old San Juan, colonial architecture meets colorful street art, and you’ll find cobblestone streets lined with boutique hotels, cafés, and historic forts. The weather in May is warm but not stifling, ideal for wandering the city or venturing into El Yunque National Forest, the only tropical rainforest in the U.S. National Forest System.

On the coast, beaches like Flamenco and Condado offer sun and surf, while the nearby islands of Vieques and Culebra are perfect for day trips. May also kicks off mango season, celebrated with food festivals that give travelers a literal taste of the island. Puerto Rico is a perfect blend of accessibility, culture, and tropical relaxation.

Why Choose Puerto Rico?

If you're short on time or simply prefer the ease of a domestic trip, Puerto Rico gives you the full Caribbean experience — no passport, no customs lines, just instant island life.

Puerto Rico Fast Facts:

• Avg. temperature: 84-86°F

• Ideal for: U.S. travelers, history buffs, nature lovers

• Highlight: No passport required, El Yunque, Old San Juan

• Arrival Airport: Luis Muñoz Marín International Airport (SJU)

Final Boarding Call

The Caribbean in May is a traveler’s dream — the crowds are down, the weather is warm, and the destinations are calling. Whether you’re sipping cocktails in Turks and Caicos, dancing through a Bahamian carnival, or discovering Puerto Rican rainforests without flashing your passport, there’s a tropical escape with your name on it.

For those flying private, each of these destinations offers a seamless arrival experience, with world-class FBOs and luxury accommodations ready to welcome you. So, where will you land this Memorial Day?