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Kosher Caribbean Travel · Midwinter Break
The Jewish community’s favorite travel season — programs, villas, and kosher infrastructure across the Caribbean, planned right.
The same room on the same dates, for less than booking it yourself.
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Where the glatt kosher is already in the building: Eden Roc Cap Cana, Grand Hyatt Baha Mar, Aruba and private villas, with this season's prices. We'll send it to your WhatsApp.
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Late January through early February, aligned with the New York and New Jersey yeshiva calendar, midwinter break has become the single largest Jewish family travel season — with dedicated kosher programs across the Caribbean and México. Families call it different things — Yeshiva Week, yeshiva break, midwinter vacation, midwinter break, or simply winter break — but it is the same week. Most programs run between January 15 and February 5. The best properties sell out months ahead.
Cinkō at Baha Mar makes Nassau the go-to for families who prefer independent travel with a certified kosher restaurant on property.
Explore the Bahamas
One of the Caribbean’s largest organized Yeshiva Week programs — glatt catering, entertainment, kids’ programming.
Explore Punta Cana
Kosher-equipped villa kitchens with chef catering — quiet, uncrowded, and beautiful.
Explore Turks & Caicos
Top properties sell out by September for January travel. We secure inventory early for our clients.
Organized programs bring meals, entertainment, and minyan on-site; private villas bring privacy with arranged catering. We plan both.
Cholov Yisroel, Yoshon, and Pas Yisroel available at select programs — we match you to your hashgacha requirements.
Babysitting, teen lounges, and organized day activities run simultaneously at all major program properties.
Full meals under Mashgiach supervision at programs — Shabbos meals are the highlight of every week.
Daily services and Torah classes at most program sites — learning and vacation in one week.
Glatt kosher provisioning arranged in advance. Shabbos logistics thought through — the practical details that make the week feel effortless instead of improvised. Suites and villas suited to families. One advisor handling all of it, end to end.
At program properties, minyanim run morning and evening and Shabbos is the highlight of the week. On an independent villa week, we plan the davening picture honestly — where Chabad is within reach, and where it isn’t. Tell us how you hold, and we’ll point you to the right island. Candle-lighting times for your destination →
Room to spread out, and every meal accounted for.
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Programs and private setups for the weeks that matter most.
Explore Pesach
The five-star escape, without compromising a single standard.
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Weddings, sheva brachos, bar & bas mitzvahs, milestone birthdays — simchas celebrated in full kosher style.
Start planningDates vary by school district — most schools take their week between January 17 and February 2. Your child’s school calendar determines the specific week, and we plan around it.
No. Many families prefer private villa stays or boutique hotel weeks. We plan both and will recommend the right approach for your family’s style.
Six months for the best options — top program spots and villa availability are gone by October for January travel.
The Bahamas for independent travel — Baha Mar’s kosher infrastructure is unmatched — or Punta Cana for the full organized-program experience.
Yes — they are two names for the same week. Depending on the school and the community you will hear it called Yeshiva Week, yeshiva break, midwinter vacation, midwinter break, or simply winter break. All of them refer to the late-January to early-February break on the New York and New Jersey yeshiva calendar, and all of them are the same travel season we plan.
