As our Twin Otter plane careens past a mist-shrouded volcano and screeches to a stop on a runway that drops into the Caribbean Sea, I’m tempted to join my fellow passengers who spontaneously burst into applause with shouts of “thank you” to our pilots. The Dutch Caribbean island of Saba is home to the shortest (and some might say the most terrifying) commercial runway in the world. While the adrenaline-boosting landing is just part of the regular work day for a Winair pilot, for the rest of us, island-hopping in the Caribbean is as much about the journey as it is about the destination.

An ideal place to begin island-hopping is at Princess Juliana International Airport (SXM), St. Maarten’s modern new gateway where Winair, the country’s national carrier, offers connections to Saba, St. Eustatius, St. Barth’s, Nevis, St. Kitts, Dominica, Guadalupe and Tortola. For those who prefer to explore by boat, the island of Anguilla is a short ferry ride away. No matter which island you choose, or mode of transportation, you’re guaranteed a collection of unforgettable adventures.

Magnetic St Maarten


Swim-out and sunset suites at Sonesta Ocean Point Resort Photo Credit Michele Peterson

For a luxurious island-hopping home base, your best bet is the new 129-room Sonesta Ocean Point Resort. Set on a dramatic promontory overlooking Maho Beach, this adults-only resort is St. Maarten’s first five-star resort and offers plenty of wow-factor, including the island’s only swim-up suites. The boutique-sized property features two other swimming pools including The Edge, an infinity pool set above a sea cave and The Point, a chic lounging zone with pool butlers and breezy views. Highlights of the all-inclusive package include 24-hour room service, the glamorous rooftop Sunset Bar and Azul restaurant offering Mediterranean-Caribbean cuisine with 360-degree views. The resort is just steps to glitzy Maho Village where you can play the slots at legendary Casino Royale, go on a pub-crawl or hit hotspots such as Bamboo Sushi and Buddha lounge. Most important for island-hoppers, it’s just five minutes to Princess Juliana Airport.

Landing at St. Barth’s Gustav III airport requires a 10° approach angle Photo Credit – SXM Airport-Alain Duzant

Joie de Vivre in St. Barth’s

Continue your high style island-hopping with a 12-minute flight to the French island of Saint Barthélemy. Landing at Gustaf III Airport is so exhilarating–it’s the world’s steepest approach–you might be tempted to have a shot of cognac once your feet hit the ground. Easily done at the nearby port of Gustavia, where you can rub elbows with the rich and famous at upscale bars, restaurants and nightclubs.


Explore the beaches of St Barth’s Photo Credit Michele Peterson

It’s a duty-free port so in addition to luxury designers such as Cartier, Chopard and Longchamp, you’ll also find hip local designers such as Poupette St. Barth’s, known for its boho-chic beachwear. But St. Barth’s is as much about its natural beauty as its pedigree so be sure to factor in time on one of its white sand beaches such as St. Jean Beach, home to the swanky Eden Rock Hotel, beloved for its sophisticated style. Your beach cabana may double as a contemporary art studio but it’s all done with French West Indies charm.

Saba: Unspoiled Adventure


Queen’s Gardens Resort on Saba offers a lush setting and spectacular views Photo credit Michele Peterson

You won’t find any beaches on Saba (pronounced Say-bah) but that shouldn’t stop you from making the 8-minute flight to Juancho E. Yrausquin airport. This tiny Dutch island packs a lot of adventure into its 13 square kilometres. Ringed by coral reef, it’s basically a submerged volcano with its peak, the aptly named Mount Scenery, the highest point in the Netherlands.

Most visitors come to explore the Saba Marine Park, a nature reserve recognized as a UNESCO World Heritage Site for its flourishing underwater sea life. Other adventures include hiking rainforest trails or touring the island’s winding stone road past villages such as Hell’s Gate, The Gap and The Bottom. In Windwardside, dine at Brigadoon helmed by Chef-Owner Tjeerd “T.J.” Abma, a French-trained Dutch chef who is one of the Caribbean’s best-kept secrets. When it’s time to retreat for the night, head for Queen’s Gardens Resort, a romantic cliffside hideaway that offers a Diving Package featuring three days of double tank diving, breakfasts, transfers, dinner and a Jacuzzi suite with panoramic Caribbean views.

Laid-back Luxury: Anguilla


Pool at Viceroy Anguilla Photo Credit Michele Peterson

It’s so easy to get to Anguilla with FunTime Charters, you might not even have time to finish your rum punch. Located in the British West Indies, a 25-minute boat ride from St. Maarten, Anguilla is composed of 33 uncrowded beaches and offshore cays.


Spend the day at Crocus Bay on Anguilla
Photo credit Michele Peterson

Find your personal paradise at the Viceroy Anguilla on Meads Bay. This stretch of pearl white beach is a magnet for celebrities, A-listers and couples drawn to its contemporary architecture, laid-back elegance and dreamy spa. Opt for a one-bedroom ocean-view suite and you’ll enjoy a spacious retreat featuring a glamorous living room with kitchenette, marble bathroom and custom-designed four-poster king bed. Best of all, it comes with its own terrace with private plunge pool where you can order room service (dining is helmed by esteemed Miami-born Executive Chef Rafael Gonzalez) and listen to the waves.

Later, as you swim in a secluded bay alongside graceful sea fans, you’ll agree that while it might be tempting to pick an island and stay put, the best way to experience the full taste of the Caribbean is by island-hopping.



Enjoy the spectacular island views on a Winair flight
Photo credit Michele Peterson

Travel Planner

Winair: Founded in 1961, Winair operates flights to 11 destinations in the Caribbean. for the rest of us, island-hopping in the Caribbean is as much about the journey as it is about the destination.

Princess Juliana International Airport: Located on the Dutch side of the island in the country of Sint Maarten, SXM’s new departures terminal includes expanded Duty Free and retail space, streamlined passenger services as well as an Executive Lounge ($20 USD) with complimentary snacks, WIFI and white wine.

FUNTIME Sea Shuttle/Anguilla Ferry: This scheduled shuttle service includes pick up at the St. Maarten Princess Juliana Airport arrivals area, luggage transfer to the private dock and preparation of customs and immigration paperwork, as well as a 25-minute luxury speedboat trip to Anguilla’s Blowing Point dock.

St. Maarten:
Saint Barth Tourism:
Saba Tourism:
Viceroy Anguilla:
Anguilla Tourist Board:
Sonesta Ocean Point:

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