Puerto Rico’s luxury calendar runs a shorter list than New York or Miami, but the events that anchor it draw HNW inbound charter every year. Below is the evergreen shortlist we plan trips around, refreshed for the 2026 season.
Puerto Rico Luxury Events Calendar
January
Fiestas de la Calle San Sebastián (SanSe) closes Old San Juan on the third weekend of January. It is a cultural anchor, not a private-jet driver on its own, but it usually falls inside a busy winter travel window.
February and March
Peak golf season at Dorado Beach (four championship courses including TPC Dorado Beach), Bahia Beach (Robert Trent Jones II), and Palmas del Mar (Rees Jones). Member-guest tournaments and corporate golf group trips dominate midsize and super-midsize charter inventory.
April
Season winds down through the month. Weather remains strong. A good window for Vieques and Culebra weekends before summer wet season starts.
November and December
Winter travel season resumes as hurricane season officially closes November 30. Thanksgiving through New Year’s fills luxury-resort inventory at Dorado Beach, St. Regis Bahia Beach, Ritz-Carlton San Juan, and the Fairmont El San Juan. Book jet lift three to six weeks ahead where possible.
Contact
For a quote, call +1-888-987-5387 or head to the contact page. Related: weddings and destination events.