Winter Sun

Which island, and how best to arrive.

The Atlantic hurricane season ends on 30 November, and by December most of the Caribbean has moved into its dry season.

For private clients, the question is rarely whether the Caribbean works in December. It is which island suits the trip, and how best to arrive. Runway length, customs arrangements and the week of travel shape the journey as much as the beach does.

Black-and-white photograph of a turboprop or very light jet on a steep short-field approach between hills towards a coas

The Islands

Choose the airport before the island.

The Caribbean has no standard airfield. Matching aircraft to island is the first decision of the trip, and it should be made before the hotel or villa is chosen.

Some islands take long-range jets direct from Europe or the US. Others have runways that rule out all but the smallest aircraft.

St Barts

December is St Barts at its most sociable, with Gustavia’s restaurants open and the harbour filling with yachts for New Year’s Eve. Getting there is part of the experience. Gustaf III Airport has a runway of roughly 650 metres and a steep approach between two hills. It is limited to turboprops and very light jets flown by specially trained crew. Most clients on larger jets land at St Maarten and make a short onward transfer by air or sea.

Turks and Caicos

Providenciales is well connected to the US, and Grace Bay’s calm, clear water suits families travelling across generations. Charter works well here for larger parties who want to fly together on their own schedule, rather than splitting across commercial departures.

Black-and-white photograph of a tender crossing open water towards an island, seen from behind the passengers, with a li

Anguilla

Anguilla offers long, quiet beaches, with Meads Bay for dining, Long Bay for space and Shoal Bay for the water. Clayton J. Lloyd International Airport has a runway of about 1,665 metres (5,460 feet), which suits turboprops and light to midsize jets, and some super-midsize aircraft. Larger jets typically land at St Maarten and complete the journey by boat. Night operations are limited, so arrival times deserve attention.

Barbados

The west coast, from Paynes Bay to Speightstown, combines calm water, beach clubs and golf at Sandy Lane and Royal Westmoreland. Barbados suits a two-week stay better than a long weekend. Its main international airport can handle larger long-range aircraft, which makes it a natural landing point for flights from Europe.

St Martin

One island, two nations. The French side offers Grand Case and its restaurants. The Dutch side is home to Princess Juliana International, the main gateway for larger private jets in the northern Leewards and the usual connecting point for St Barts and Anguilla. For groups who like to dine out, it is also a destination in its own right.

Punta Cana

The airport is a short drive from the resorts and residences of Cap Cana and Puntacana Resort, which makes this one of the simplest December trips from the US East Coast. It is a sensible choice for a first Caribbean charter.

Casa de Campo

On the Dominican Republic’s south coast, this gated resort has its own marina, beach club and the Teeth of the Dog golf course. Once you have landed, a family can spend a week with very little onward travel.

Black-and-white photograph of a private jet on a Caribbean apron at dusk, ground crew loading luggage, palms silhouetted

Timing the Season

Two holidays, each with its own rhythm.

Christmas week and New Year’s week are two different holidays. Fixing the aircraft early, and staying flexible by a day either side of the peak, usually widens the choice and protects the schedule.

The busiest days for private aviation tend to be the run-up to Christmas and the first days of January.

What to settle before you fly

  • Which aircraft suits the runway at your final destination, and whether a connecting island is needed
  • Customs and immigration arrangements on arrival, which differ by island and jurisdiction
  • Airport operating hours, as some Caribbean airfields restrict night operations
  • The onward transfer, whether by road, boat or helicopter
  • Return timing, so the homeward leg is as carefully planned as the outbound one

The Oryx Perspective

Access over assets.

A December in the Caribbean rarely follows a single route.

One week may call for a long-range jet into Barbados, the next a smaller aircraft into Anguilla or a connection through St Maarten to reach St Barts. Charter lets each sector be matched to the runway, the party and the day, without the compromises of a single aircraft chosen in advance. For clients who value access over assets, that flexibility is the point.