Direct Flights to the Caribbean from the US and London, Winter 2026-27.

Direct flights to the Caribbean this winter run from New York to almost every island with a private villa worth the trip, from Miami to more than twenty Caribbean destinations, most in three hours or less, from Boston to twelve islands, from Atlanta to ten on Delta, and from London to Barbados, Antigua, St Lucia, Jamaica, Punta Cana and Bermuda. St Barts and Mustique have no nonstop and are reached by a short connection. Below, the routes city by city, with the flight times, and our Caribbean villa rentals at the other end.

Direct flights to the Caribbean at a glance

From airline announcements and published schedules in October 2026, rounded. Many routes run only in winter or a few days a week; we confirm the flight for your dates.

Direct flights from New York

New York has the widest choice, and Newark is now part of it: from December 18 AnguillAir flies nonstop from Newark to Anguilla on Mondays and Fridays, and adds a Wednesday and Saturday flight via Providenciales. Cayman Airways ends its JFK service on October 19, 2026, so Grand Cayman is now JetBlue, Delta and United. For a weekend, our guide to short flights from New York to the beach puts the islands next to Nantucket, Bermuda and Miami.

Direct flights from Boston

Logan has nonstops this winter to Turks and Caicos, Anguilla, St Martin, Barbados, the Dominican Republic, the Bahamas, Jamaica, Grand Cayman, Aruba, St Lucia, San Juan and St Thomas, most of them on JetBlue, with Delta and American adding winter flights and BermudAir flying to Anguilla and Turks and Caicos. Our guide to direct flights from Boston to the Caribbean has the airlines, days and flight times island by island.

Direct flights from Miami

Miami is the Caribbean’s gateway: American alone flies to more than twenty Caribbean destinations from there, and the shortest flight is under an hour. Our guide to short flights from Miami orders them by flight time, with what happens after you land.

Anguilla: three ways in, nonstop

This winter Anguilla has nonstops from four US airports: American from Miami, a route it has flown since December 2021, in about three hours; and from mid-December BermudAir’s AnguillAir from Boston and Newark on Mondays and Fridays and from Baltimore-Washington on Mondays. From San Juan, Tradewind flies to the island daily from December 10 to April 12, and Cape Air flies daily from St Thomas. Most of our guests still fly to St Martin and cross by private boat in about 25 minutes. See our Anguilla villa rentals and our guide to how to get to Anguilla.

The Beach House

Meads Bay · 8 bedrooms · sleeps 16

Directly on Meads Bay, with an infinity-edge pool, a tennis court, a children’s play area, and rowing boats and paddleboards at the water. Fully staffed, with private chefs, a property manager, daily housekeeping and a member of staff on hand around the clock.

Direct flights from Atlanta

Delta also flies from Atlanta to Aruba and to Liberia in Costa Rica. Our guide to where you can fly from Atlanta has the full list.

Direct flights from London

British Airways also flies daily from Heathrow to Bermuda, in about seven and a half hours. There is no nonstop from London to Turks and Caicos or Grand Cayman: British Airways flies to both through Nassau. Virgin Atlantic’s Antigua flights touch down in Barbados on the way.

Islands you reach by a short connection

St Barts has no nonstop from the US mainland: its runway takes only small aircraft. Fly to St Martin and take a flight of about fifteen minutes on Winair or St Barth Commuter, or a ferry of about 45 minutes; Tradewind also flies from San Juan and Antigua, and Cape Air from St Thomas. Mustique is reached through Barbados or St Vincent. A private charter is the most seamless way onto either, and we arrange it with the villa: see our St Barts villa rentals and our guide to flights to St Barts.

Plan your Caribbean trip

Best time to visit

The Caribbean is warm all year, and the dry season runs from December to April, which is also when the airlines fly the most. May, June and November are quieter, with more choice of villas. The Atlantic hurricane season runs June 1 to November 30. Book Christmas, New Year and Easter nine to twelve months ahead, and January to March six to nine months ahead; shoulder and summer dates can often be confirmed within 60 days.

Passports and currency

US citizens need a passport for every island on this page except Puerto Rico and the US Virgin Islands. The US dollar is the official currency in Turks and Caicos and the US Virgin Islands and is widely accepted elsewhere, alongside the Eastern Caribbean dollar (in Anguilla, Antigua and St Lucia, among others), the Barbados dollar and the Jamaican dollar; St Martin’s French side and St Barts use the euro.

Travel insurance

Arrange it when you book, so it covers the flights and the villa from the start: cancellations, medical care and missed connections, which matter most when the last leg is a small aircraft or a boat.

More Caribbean guides

• Direct flights from Boston to the Caribbean
  Twelve islands, airline by airline.
• Short flights from Miami
  Nine island escapes, by flight time.
• Short flights from New York to the beach
  From Nantucket to Anguilla.
• How to get to Anguilla
  The new nonstops and the boat from St Martin.

Direct flights to the Caribbean: your questions answered

Updated October 2026. Sources: American Airlines, Bahamas Ministry of Tourism, BermudAir, British Airways, Caribbean Journal, Cayman Airways, and the airlines’ published schedules in October 2026. Schedules change by season; we confirm the flight for your dates.