First-Class Island Hopping

1 Passenger

Passengers

Infants (Under 2)

From

1 Passenger

Passengers

Infants (Under 2)

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.

Visit our Know Before You Go page for important travel tips and information to help make your trip with Tradewind seamless and stress-free.

The Experience

Convenient Transfer Hubs Interline Partners Private Jet Connections

Convenient Transfer Hubs

Fly through San Juan, PR and easily connect with virtually all major airlines from the U.S. Direct flights from Canada, Europe and South America are also available. Fly to Antigua from London on British Airways or Virgin Atlantic for a convenient one-stop transfer to St Barths.

All Tradewind guests connecting through San Juan can relax and enjoy refreshments and complimentary WiFi in our private lounge. Lounge hours are between 8:00AM to 6:00PM from June through October, and between 6:00 AM and 6:00 PM from November through May. Once ready for boarding, guests are escorted through expedited security screening and directly out to the awaiting aircraft.

Interline Partners

Tradewind has ticketing and baggage transfer agreements with American Airlines, United Airlines, JetBlue Airways, and British Airways. Book interline travel with your travel advisor or directly with the airline for a smooth transfer with luggage transfer to St Barths, Virgin Gorda, Tortola, Anguilla, and Antigua.

Private Jet Connections

Connecting from another private jet? Our team will meet your aircraft arrival for a smooth transfer to your awaiting Tradewind connection.

Map of Caribbean routes connecting San Juan, St. Thomas, Virgin Gorda, Tortola, Anguilla, St. Barths, and Antigua

Scheduled Connections

Tradewind offers scheduled connections throughout the Eastern Caribbean. Fly with confidence to your next destination.

Flights are now available for booking through May 2025.

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.

INQUIRE