Flights from your city to the Caribbean for Presidents' Day weekend
Where to fly from your city to the Caribbean for Presidents' Day weekend: fares for Presidents' Day weekend 2027 (Feb 12 to 16) to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.
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Dates: Presidents' Day weekend 2027, Feb 12 – Feb 16, 2027.
Choose your departure city
Each city page shows real round-trip fares from that city, with the cheapest one for each destination.
United States: Seattle · New York · San Francisco Bay Area · Los Angeles · Miami or Fort Lauderdale · Chicago · Denver · Minneapolis · Houston · Washington, DC · Dallas-Fort Worth · Atlanta · Orlando · Las Vegas · Charlotte · Phoenix · Boston · Detroit · Philadelphia · Salt Lake City · San Diego · Nashville · Tampa · Austin · Honolulu · Portland · Raleigh/Durham · Saint Louis · Sacramento · San Juan · New Orleans · Kansas City · Fort Myers · San Antonio · Indianapolis · Cleveland · Pittsburgh · Columbus · Cincinnati · West Palm Beach · Jacksonville · Maui · Hartford · Charleston · Milwaukee · Anchorage · Boise · Omaha · Albuquerque · Buffalo · Richmond · Norfolk
Where to go and why
- Punta Cana: Punta Cana's long white-sand beaches and all-inclusive resorts
- Montego Bay: Jamaica's resort coast around Montego Bay and Negril
- Nassau: Nassau and Paradise Island, a short flight from the East Coast
- Aruba: Aruba's dry, sunny weather outside the hurricane belt
- San Juan: Old San Juan, beaches and the rainforest, no passport needed from the US
- Grand Cayman Island: Seven Mile Beach and world-class diving on Grand Cayman
- Providenciales: Grace Bay in Turks and Caicos, one of the Caribbean's best-known beaches
- Saint Thomas: St. Thomas beaches and an easy ferry to St. John, no passport needed from the US
- Sint Maarten: St. Martin, two countries on one island with plenty of beaches
- Curacao: Curaçao's calm coves for snorkelling and colourful Willemstad
- Bridgetown: Barbados beaches on the calm west coast and surf on the east
- Saint Lucia: St. Lucia's Pitons, rainforest and resort beaches
- Antigua: Antigua, a beach for every day of the year
- Kingston: Kingston, Jamaica's capital, with the Blue Mountains nearby
- Santo Domingo: Santo Domingo's colonial zone, the oldest city in the Americas
- Saint Croix: St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the US
Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027