The U.S. Department of Homeland Security has temporarily suspended Global Entry. We recommend allowing additional time for screening and customs when flying to/from the Caribbean. For any questions, please contact our team at 203-267-3305 option 1.
An elevated travel experience in the Caribbean.
Flights are operated by Tradewind in a modern fleet of Pilatus PC-12 aircraft flown by two pilots from convenient transfer hubs. In San Juan, enjoy the Tradewind private lounges and VIP Experience available for purchase.
For year-round connectivity, passengers from New York, Boston, and other mainland cities can reach San Juan via interline partners including American Airlines, United, and JetBlue, then connect seamlessly to Tradewind’s Caribbean network.
Visit our Know Before You Go page for important travel tips and information to help make your trip with Tradewind seamless and stress-free.
Scheduled Connections
Tradewind offers scheduled connections throughout the Eastern Caribbean. Fly with confidence to your next destination.
Flights to St Barths are now available for booking through January 19th, 2027.
Flights to Anguilla are available through April 20, 2026, and flights to Virgin Gorda and Tortola through May 15, 2026, in addition to special flights to Virgin Gorda for “Xmas in July” from July 19th through July 26th, 2026.
VIP Experience in San Juan
Opt for our popular VIP Experience in San Juan for your transfer between flights. A Tradewind representative will meet you at the arriving airline gate and escort you to the Tradewind private lounge. Luggage is retrieved by a Tradewind representative and checked in while you relax in comfort and style. ($300 per group if all arriving on the same commercial flight.)
While we are unable to offer a VIP Experience for return flights to San Juan, all Tradewind guests are met by our team in immigrations and customs and directed to their connecting airline check-in areas.
VIP Experience is only available in the San Juan Airport.
FREQUENTLY ASKED QUESTIONS
The most common route to St Barths from the U.S. is to fly into San Juan, Puerto Rico (SJU) and connect to Tradewind’s scheduled service to St Barths (SBH). Tradewind operates daily flights from San Juan, with a flight time of roughly 50 minutes on a Pilatus PC-12 turboprop. Major airlines including American, United, and JetBlue offer frequent nonstop service from U.S. cities to San Juan.
There are no direct commercial flights from the U.S. mainland to St Barths. The runway at Gustaf III Airport (SBH) is too short for large jets, so all flights arrive on smaller aircraft. Tradewind operates scheduled service from San Juan, Antigua, and St Thomas, offering the most convenient connections. Charter flights from other Caribbean islands are also available.
Tradewind offers scheduled flights from San Juan (SJU) to Anguilla’s Clayton J. Lloyd International Airport (AXA). The flight takes approximately 45 minutes. Many travelers fly into St. Maarten (SXM) and take a ferry to Anguilla, but that route requires clearing customs twice, depends on ferry schedules, and can add hours to your trip. Tradewind’s direct flights from San Juan skip all of that, with private lounge access in SJU and a seamless door-to-door experience.
Tradewind flies scheduled service from San Juan to both Tortola (EIS) and Virgin Gorda (VIJ) in the British Virgin Islands. Tortola flights land at Terrance B. Lettsome International Airport, while Virgin Gorda service arrives at the island’s compact airstrip. Both routes take just over a half hour from San Juan. This eliminates the need for a ferry transfer from St. Thomas, which can add hours to the journey.
Tradewind’s VIP Experience at San Juan Airport includes access to a private lounge, expedited check-in, and personal assistance with luggage and connections. The service is designed to make the transition between your mainland flight and your Caribbean island flight as smooth as possible, with complimentary refreshments and a comfortable waiting area away from the main terminal.
Yes. Tradewind has interline agreements with American Airlines, United Airlines, JetBlue, allowing passengers to book connecting itineraries from U.S. mainland cities through San Juan to Caribbean destinations on a single ticket. This means your bags can be checked through automatically and your connections are conveniently scheduled. It is an especially convenient option for travelers from Northeast hubs like New York (JFK, LGA, EWR), Boston (BOS), and Washington, D.C. (DCA, IAD).
UK travelers can also connect via British Airways through Antigua (ANU).