Destinations / Caribbean
The Caribbean,
when it is winter
Private island villas, beachfront retreats, yachts and relaxed family hospitality — for the weeks of the year when Europe is not the answer.
Why here
The Caribbean does one thing very well: it gets a family somewhere warm, private and beautiful in the middle of winter, with a short flight from the East Coast. For Chanukah, February half-term or a winter Shabbat weekend, nothing else is close.
The catch is that the kosher supply chain is thin to non-existent on most islands, and it varies enormously between them. St Barths is not Anguilla is not Turks and Caicos. Which island we recommend is driven as much by what can be provisioned as by what the villa looks like.
So we ship. Meat, wine, dry goods and specialty items are consolidated and sent ahead, produce and fish are sourced locally within the standard, and the kitchen is built before the family lands. It is a logistics exercise, and it is entirely solvable.
Where, within it
The regions
worth choosing between.
St Barthélemy
The best villa stock in the Caribbean and the most reliable supply chain. The default recommendation for a first winter trip.
Turks & Caicos
The best beach, the calmest water, and strong for families with young children. Excellent villa-and-yacht combinations.
Anguilla
Quieter and less seen than St Barths, with exceptional beaches and genuinely private properties.
The British Virgin Islands
The strongest charter waters in the region — short passages, protected anchorages, ideal for a first family charter.
The Bahamas & the Exumas
Close to Florida, superb for yachts, and the easiest region to provision from the United States.
Barbados & the southern islands
Larger, more developed, more to do beyond the beach. Better for longer stays.
When it's actually good
December–April
The season. Chanukah, the winter school breaks and Pesach are the tightest weeks — book nine to twelve months out.
May & June
Excellent value, still reliably good weather, and far quieter.
July & August
Hot and humid; workable, and much less expensive.
September & October
Hurricane season. We do not recommend it and will say so plainly.
How it's produced
The practical
shape of it.
Properties
- Beachfront and hillside villas with full staff
- Private estates and small resort buyouts
- Motor yachts and catamarans for island-hopping
- Villa-and-yacht programmes across a single stay
- Properties with separate guest houses for multi-family groups
Culinary
- Fish and seafood within the standard, from the day boats
- Caribbean cooking done properly rather than as a resort gesture
- Outdoor grilling and beach lunches as the centre of most days
- Tropical produce, which is a genuine pleasure and entirely local
- Long Friday-night tables outdoors, which is the best meal of most Caribbean weeks
Kosher setup & provisioning
- Villa kitchens kashered before arrival, with dedicated equipment brought in
- Meat, wine, dry goods and specialty items shipped ahead and consolidated
- Produce, fish and dairy sourced locally within the agreed standard
- Island selection driven partly by what can actually be supplied
- Mashgiach travelling with the group for the duration
Shabbat, Yom Tov & Jewish life
- Shabbat produced entirely privately on most islands
- Historic synagogues in Curaçao, St Thomas, Barbados and Nevis — among the oldest in the Americas
- Minyan formed from the group; small communities on a few islands
- Walking distances and property layout checked before a villa is taken
Getting there
- Gateways: St Maarten and St Barths, Providenciales, Antigua, Nassau, Barbados, San Juan
- Most islands require a connection or a private leg — build a travel day in each direction
- Yacht charters usually start from Tortola, Nassau or St Maarten
- Provisioning shipments need two to three weeks of lead time and customs planning
Journey styles in the Caribbean
