Tradewind Aviation Extends Caribbean Flights Through Spring 2027, Including Virgin Gorda, Tortola, and Anguilla

By: - July 29th, 2026
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The Baths in Virgin Gorda.

Tradewind Aviation has opened reservations for additional Caribbean flights through Spring 2027, giving you an early opportunity to plan winter and spring getaways to several of the region’s most popular islands.

The carrier has added booking availability for seasonal service from San Juan, Puerto Rico to Virgin Gorda, Tortola, and Anguilla, with flights operating during the peak winter travel season.

The San Juan-Virgin Gorda route will operate daily between Nov. 19 and April 12, while daily service from San Juan to both Tortola and Anguilla will run between Dec. 10 and April 12.

The schedule continues to strengthen San Juan’s role as one of the Caribbean’s most important regional aviation hubs, offering convenient onward connections from major U.S. gateways to islands that typically require a smaller aircraft for the final leg of the journey.

Tradewind also confirmed that its popular routes to St. Barth from both San Juan and Antigua are now available for reservations through April 30.

The airline has become one of the leading carriers for premium regional travel in the northeastern Caribbean, operating scheduled flights alongside private charter service. Its network connects several destinations that are not served by larger commercial airlines, making it a popular choice for travelers heading to destinations including the British Virgin Islands, Anguilla, and St. Barth.

The newly released schedule gives travelers several additional months to secure winter and spring travel dates, particularly during the busy holiday and high-season period, when flights to the northeastern Caribbean often sell out well in advance.

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