When to Book Flights for a Caribbean Charter

Airfare into Caribbean gateway airports tends to move in cycles tied to the winter high season, so booking three to five months ahead usually beats waiting for a last-minute deal.

Lock in your charter dates first, then work backwards — most travelers fly in a day early to account for connections and to enjoy a night ashore before boarding.

Tuesday and Wednesday departures are frequently the least crowded and, in our experience, the easiest to find good connection times on.