The Holidays

Tighter than the Caribbean, in practice. Chalets are let by the week and the best are held by returning families a year ahead, so what appears late is usually a cancellation rather than an opening. Worth asking, and the answer comes quickly.

Above the Arctic Circle, while they are still the right age for it — Tromsø and Finnish Lapland give you reindeer, huskies and the aurora. Skiing rarely repays a party whose youngest is under six.

It divides on what the days should look like, not on budget. The Alps put the whole party in one house with something to do at the door; the Caribbean puts them on one beach with nothing that has to be done at all.

Ten to fourteen nights. It absorbs the travel days at both ends and leaves the middle genuinely unhurried, which a seven-night week over the holidays does not.

The best houses commit in the spring, and returning guests hold many before they are ever offered. For a specific villa on a specific island, April or May is the difference between choosing and being allocated.

Yes, and in 2026 it is the easier window. Hanukkah runs from sundown on 4 December to nightfall on 12 December, two and a half weeks before the Christmas fortnight; the first candle is lit on Friday 4 December before sundown, because Shabbat begins that evening. The houses are the same; the competition for them is not. The mountains are just open, Aspen since 26 November and Courchevel from 4 December, and the Caribbean is past the end of hurricane season on 30 November.

Three things change rather than one. Alpine chalets are let by the week and the peak week is priced apart from the rest of the season; Caribbean villas are let by the fortnight across the turn of the year, so ten nights and fourteen often come to the same; and minimum stays lengthen across the board. Our planning fee is US$250 and is charged in every case, before anything is held.

Yes, as part of the planning rather than on arrival. Kosher catering in a private house is arranged before the household arrives: whether it comes from a certified caterer or a supervised kitchen, and how the house's own chef works alongside it, depends on the destination, so your advisor confirms it in writing before the house is held. In 2026 the first night is Friday 4 December, so the house is set up for the first candle and for Shabbat on the same evening.

A Caribbean villa over the holidays usually carries New Year inside the same booking because the best villas are let by the fortnight across the turn of the year. A household taking one for Christmas is therefore already there for New Year, on one beach with nothing that has to be done at all. It also means ten nights and fourteen often come to the same, which makes the longer stay the natural choice.

Turks & Caicos is where a Caribbean holiday villa lands when the party includes children and the water is meant to be the point. It trades the snow for a beach, and because the best villas there are let by the fortnight, the New Year sits inside the same booking. Hurricane season has ended by 30 November, so the Caribbean is settled well before the Christmas fortnight.

A staffed chalet in Zermatt puts the whole party under one roof with the mountain at the door, so there is always something to do without leaving the house behind. Zermatt and Aspen are where a holiday chalet usually lands. Chalets are let by the week, the peak week is priced apart from the rest of the season, and the best are held by returning families a year ahead.

The best staffed houses for the last fortnight of December are committed long before the season opens, so what is left is rarely what is published. Returning guests hold many before they are ever offered, and in the Alps a chalet that appears late is usually a cancellation rather than an opening. With fixed dates and a full household, it is worth asking directly rather than relying on what is advertised.

Over the holidays, the choice is usually snow or sea. On the snow side, staffed chalets in Zermatt and Aspen, let by the week and often committed a year ahead; with young children, Tromsø and Finnish Lapland above the Arctic Circle. On the sea side, staffed villas in Turks & Caicos, St Barth or Barbados, held for ten to fourteen nights so that New Year sits inside the same booking.

Because an advisor opens what no platform can sell. Online platforms list what's already public — the same rooms and flights available to everyone. A Forest advisor opens what isn't: private after-hours access, the host who answers because they know us, pacing built around your life, and logistics that stay invisible. Over forty years we've built the relationships that turn 'impossible' into 'it's arranged.'

It begins with a conversation, not a quote. A dedicated advisor learns how you want to feel — not only where you want to go — then designs a journey around you and reshapes it freely as your plans evolve. There's no fee for the initial consultation and no obligation.

Discretion is built in. We work quietly, share nothing, and arrange private transfers, exclusive-use stays and after-hours access so you're never on public display. For clients who require it, every detail is handled under strict confidentiality.