Where do the wealthy go in winter?

They split the season — sun in the Maldives, the Caribbean and the Seychelles, and snow in the Alps, with private chalets in St. Moritz, Courchevel and Aspen. We arrange either, or both in one trip, in the finest luxury hotels and chalets in each.

Where is the best winter sun in December and January?

For reliable warmth: the Maldives, Seychelles, the Caribbean, and parts of Southeast Asia and the Middle East. We steer you to the clearest skies and calmest seas for your exact dates, in the finest luxury resorts and villas.

How much does a luxury winter trip cost?

As an indicative guide, a luxury winter escape typically starts from around US$2,000 per night for a chalet or beach villa, rising with private aviation and exclusive use. We share a starting range candidly and never quote a final, all-in price until the trip is designed.

Can you arrange a private ski chalet with full staff?

Yes — catered chalets in the finest Alpine and North American resorts with private chef, in-resort ski guiding, and ski-in/ski-out access, the whole chalet yours, arranged through relationships in resorts that book out a year ahead.

Can we combine winter sun and snow in one trip?

Yes — a popular pairing is a week of Alpine skiing followed by a beach finale, or vice versa, with private flights connecting the two so the transition is seamless.

What does a luxury ski trip include?

Typically the chalet or finest hotel, private chef, ski guiding and lift access, equipment and transfers; helicopter access and off-piste guiding are arranged to your plan. Details are discussed openly upfront.

How far ahead should we book for the holidays and peak ski weeks?

Nine to twelve months for Christmas, New Year and February half-term, when the finest chalets and beach villas sell out first. Early commitment secures the property, the dates and the private transfers.

Where do families go for winter sun with children?

The Maldives, the Caribbean and the UAE balance reliable warmth with the finest family-friendly resorts and villas, vetted childcare and short-enough flights — all arranged to keep the journey effortless.

Where the Discerning Travel in Winter — Guaranteed Sun and the Finest Snow

Winter divides the world into sun and snow, and the finest of both are booked early and privately. Here is where to go in December through February, and what it typically starts from.

Curated by Juan David· Travel Agent, Forest Travel· Updated June 2026

Key takeaways

For guaranteed winter sun: the Maldives, the Seychelles, the Caribbean's leeward islands, and French Polynesia, which stays warm year-round.
For the finest snow: private chalets in the Alps and heli-access in remote ranges, in the best luxury hotels and chalets in each resort.
December through February is peak demand — the finest villas, chalets and suites are held months ahead.
Privacy is the difference: villa and chalet buy-outs with their own staff, away from the festive crowds.
Indicative starting point: a luxury winter villa or chalet typically starts from around US$5,000 a night.

Where the discerning go for winter sun

When the Northern winter sets in, the reliable warmth is in the Indian Ocean — the Maldives and Seychelles — and the Caribbean's leeward gems, while French Polynesia stays warm year-round. From roughly December to February these are at their finest. We match the destination to your dates and place you in the best luxury hotels and villas in each.

And for the finest snow

For those who chase winter, we arrange private chalets in the great Alpine resorts and heli-access in remoter ranges — the best luxury chalets and hotels, with private guides and the season's best weeks reserved well ahead.

Book early — winter is peak

December through February is the most contested window of the year. The finest villas, chalets and suites are held months in advance; the earlier we begin, the more can be reserved exclusively for you.

Privacy over the festive crowds

The real luxury in high season is seclusion — villa and chalet buy-outs with their own staff, private transfers, and access that keeps you away from the crowds the season draws.

What it typically starts from

As an indicative guide, a luxury winter villa or chalet typically starts from around US$5,000 a night, rising with full buy-outs, private staff and aviation. We share a starting range early and never quote a final, all-in figure until the trip is designed.

Common Questions

Questions, answered.

Explore the journeys

Escape Winter Entirely

See the collection →

Tell a private advisor how you like to travel — no quotes, no obligation.

Begin Your Private Consultation

Photograph: Shai Pal / Unsplash