caribbean fly private
A Tradewind Citation CJ3 jet.

How to Fly Private to the Caribbean

By: Alexander Britell - April 23, 2021

Since the onset of the pandemic, demand for private air travel has surged worldwide, as travelers look to the safety and luxury of private aviation. 

That’s particularly true in the Caribbean, where private airports abound and choosing a private carrier can often be the best (and only) way to reach certain sought-after destinations. 

So what’s the process actually like? And how do you go about booking a private flight in the Caribbean? 

To learn more, Caribbean Journal caught up with David Zipkin, co-owner and Vice President of Tradewind Aviation, one of the world’s leading private jet companies and a major aviation force in the Caribbean. (Tradewind also offers scheduled commercial service to a number of destinations, most notably the island of St Barth). 

How has the pandemic changed the demand for private jet travel?

The pandemic has changed private aviation in several ways.  First, there is more overall demand driven by the desire to avoid exposure to the virus in airports and airlines.  Additionally, we have seen a 50 percent increase in new to private travel since the pandemic began. Another shift is in travel patterns.  People have more schedule flexibility so we are seeing less pressure on traditionally busy days and more demand at off times.  We expect this trend to continue through at least the summer with remote work continuing or many people. 

Are you seeing different customers than you used to? 

Yes, we have seen a significant increase in new to private travel clients. We are particularly well positioned for this as our Pilatus PC-12 private flights offer a lower price point vs your traditional private jets.

Where does Tradewind fly in the Caribbean, both regularly scheduled and charter? 

We offer private charter flights throughout the Caribbean in our fleet of Pilatus PC-12s.  We can fly anywhere to and from the U.S. islands; Puerto Rico, St Thomas, St Croix and our more popular destinations are St Barths, Anguilla, Nevis, and the BVI.  We also offer private jet flights to the Caribbean in our fleet of Citation CJ3 jets.

Inside a Citation CJ3 jet.

Let’s say I live in New York or Miami. What are my aircraft options for flying privately to the Caribbean?

From New York or Miami, an excellent option is to fly private to the Caribbean in one of our Citation CJ3 jets.  If the destination has a small runway, we will do a seamless “wing to wing” transfer to one of our Pilatus PC-12 aircraft for quick hop to smaller island.

What if I’m going to an island like St Barth? Can I book both legs with you? 

Yes, we offer the full trip with both aircraft and the seamless “wing to wing” transfer.  Additionally, we have several promotions in place with top properties and villa rental agencies offering complimentary catering, ground transportation and special amenities at the destination.

caribbean travel awards 2021
A Tradewind Pilatus PC-12.

Do you work with any Caribbean villa companies or hotels on flight/accommodations packages? 

We do!  A full round-up of current promotions can be found here:  We have promotions in place with WIMCO villas, the Carl Gustaf hotel, Le Barthelemy hotel. Hotel Manapany, Le Toiny, Villa Marie, St Bath Properties and Le Sereno on St Barth.  To Anguilla we have a promotion in place with the Belmond Cap Julica and the Four Seasons.

What’s the typical pricing structure for a round trip to the Caribbean? 

Pricing is highly dependent on routing.  Maimi to the eastern Caribbean (Puerto Rico, BVI, St Kitts) will run around $16-19k each way.  For closer destinations like the Bahamas and Turks and Caicos the pricing drops to $10-$15k each way.

David Zipkin, vice president and co-owner of Tradewind Aviation.

Do you offer any memberships or club options? 

We do!  Our most popular program is our Goodspeed card which offers discounts of up to 15% on our Pilatus PC-12 fleet.  The two service regions are 300 miles from San Juan and Westchester airport in the Northeast.

Private jet travel naturally seems safer right now. What are some of the other measures trade wind implements to ensure guest safety? 

We have implemented strict protocols and procedures to ensure the health and safety of our passengers and crew from additional aircraft cleaning (deep cleaning at night and disinfecting between each flight) to pre-flight passenger screening, mask protocols, crew health checks.  Additionally, it is worth pointing out that the cabin air on Tradewind aircraft is renewed continuously with fresh air from the outside during the flight.  Air entering the cabin is compressed and heated by the engine, killing any airborne germs before cooling to cabin temperature. Our aircraft exchange interior cabin air every 2 to 6 minutes.

For more, visit Tradewind Aviation.

Popular Posts cape santa maria

The Best Caribbean Beach Resort You’ve Never Heard of 

There’s a boat just offshore called “Escape.”  It’s bobbing in some of the most brilliant, dynamic turquoise water I’ve ever seen, a few meters from a stretch of sand so bright and so white you have to squint to look […]

Marriott Is Opening Its New St Regis Resort In Aruba 

aruba st regis inside the restaurant with chairs

It was more than a decade ago that Marriott opened its first-ever Ritz-Carlton resort in the Dutch Caribbean: the Ritz-Carlton, Aruba, which at the time was the island’s first true five-star resort.  Fast forward to 2024, and Marriott is set […]

From All-Inclusive Resorts to Beaches, Travelers Are Falling in Love With Antigua and Barbuda

antigua barbuda frontier airlines the peninsula with sand

The plunge-pool villas at Hammock Cove. The historic streets of Nelson’s Dockyard. Pool days at Sheer Rocks. Unforgettable honeymoons. Vibrant meals of pepperpot and fungee. Beach bar hopping on the south coast. Endless serenity in Barbuda.  Travelers keep flocking to […]

Related Posts beach at the mousai

The Future of Tour Operators in the Caribbean

This summer, ALG Vacations (ALGV) will be launching Luxe by ALG Vacations, a comprehensive luxury travel program designed to cater to a high-end clientele. Many advisors feel this move is yet another indicator that the tour operator business has become […]

In Grenada, the Caribbean's Best New Luxury Resort

grenada view of resort

Your suite or villa comes with its own pool. All of them do. Every single suite at the new Six Senses in Grenada is nearly 600 sq ft with an expansive deck looking out at the lagoon, the bay or […]

Royal Caribbean Has Another New Cruise Ship, With Short Getaways in Mind  

pool deck with canopy on cruise ship

If you’re planning on a summertime cruise to the Caribbean, Royal Caribbean has another new option for you: the ambitiously-named Utopia of the Seas, which is headed to Port Canaveral for a July launch.  The massive new ship officially joined […]


Sign up for Caribbean Journal's free newsletter for a daily dose of beaches, hotels, rum and the best Caribbean travel information on the net.

No. Thank You