The journal · October 28, 2026

The Winter Season: Ten Places to Fly, December to March

Winter splits the private calendar in two: the snow and the sun. Christmas and New Year’s week is the busiest of the year for private aviation, and the best aircraft, villas and suites are spoken for months ahead. Here is where our clients go, and what to know before you book.

1. St Barts

Christmas and New Year’s week is the peak of the winter calendar, with the yachts anchored off Gustavia. Jets land at Princess Juliana on St Maarten, and a short island hop finishes the journey. Rosewood Le Guanahani, Eden Rock and Cheval Blanc are the key hotels. Flying to St Barts

2. Aspen

The American ski capital, with peak demand over the holidays and Presidents’ Day. The Little Nell and the St. Regis are the grand hotels, but villa rentals dominate. Aspen’s mountain airport has size limits and fills fast, so we always plan Eagle County as the back-up. Flying to Aspen

3. Courchevel 1850

Europe’s most exclusive ski resort, with an international crowd. Aman Le Mélézin, Cheval Blanc and Les Airelles lead. Fly into Chambéry or Geneva and finish by helicopter. Flying to Courchevel

4. St Moritz

Old-money Swiss glamour, with snow polo and the White Turf horse races on the frozen lake in February. Badrutt’s Palace and Suvretta House are the classics, and Samedan airport is five minutes away. Flying to St Moritz

5. Gstaad

Quieter and very private, with more chalet owners than visitors. The Alpina and the Gstaad Palace are the main hotels. Most jets land at Bern, around an hour away. Flying to Gstaad

6. The Maldives

The warm-weather alternative, especially popular with families over the holidays. Four Seasons Landaa Giraavaru, Cheval Blanc Randheli and Soneva Jani lead, each reached by seaplane or yacht from Malé. Flying to the Maldives

7. Palm Beach and Miami

The season runs from December to April, and Art Basel Miami Beach in early December is the kick-off. Palm Beach is around two and a half hours from New York, and Miami an hour south. Flying to Palm Beach · Flying to Miami

8. Dubai

Peak season runs from November to March. One&Only, Four Seasons and Bulgari are the key properties, and an ultra-long-range jet flies from New York nonstop. Flying to Dubai

9. Los Cabos

Easy jet access from the West Coast and New York, with a dedicated private aviation airport at Cabo San Lucas. One&Only Palmilla, Las Ventanas and Montage lead. Flying to Los Cabos

10. Mustique

An ultra-private island of villas, with a royal and rock-star pedigree: the alternative for those who find St Barts too busy. Jets land at Barbados or St Vincent, and a small aircraft makes the last hop. Flying to Mustique

When to book

For Christmas and New Year, start planning in the summer. Aircraft, airport parking, helicopter slots and the best villas go first, and late requests often mean a larger aircraft or a longer transfer. For Presidents’ Day and February in the Alps, book by early autumn.

Tell us where you would like to spend the season. We will arrange the flight, the last-mile transfer and, through Le Rambouillet, the villa or suite.

Plan this journey

Beyond the flight

Beyond the flight

With our sister concierge, Le Rambouillet, the whole journey can be arranged: suites at partner hotels, villas, superyachts and a private chef waiting on arrival.

Arrange a journey