Beach in Turks and Caicos (Photo: Envato)
Many families plan their winter getaways around “Yeshiva Week.” With January and February bringing serious cold to the East Coast, it’s no surprise that kosher travelers start looking for warm, sunny destinations. There’s no single Yeshiva Week schedule — every city and even individual schools take their break at different times — but most fall somewhere between mid-January and the first week of February. It’s the perfect time to escape and explore kosher-friendly winter vacations.
Growing up in New York, the options for Yeshiva Week were pretty limited. Most people went to Grossinger’s (until it closed in 1986) or to Florida. Nobody talked about flying abroad. I’m from New York. We didn’t learn geography. There was New York… and then everywhere else. Today, we live in a global society where everyone is more connected, and the internet has opened our eyes to other cultures and new destinations. Still, I’m sure plenty of New Yorkers believe the world revolves around them.
And kosher food? Winter vacations in the 1980s meant packing tuna fish sandwiches for trips to Disney World. Kids today don’t realize how good they have it, with kosher restaurants and Chabad centers in so many vacation hotspots.
This year, I’m highlighting the most popular warm-weather kosher vacation destinations for winter 2026: Panama, the Caribbean islands, Florida, and Mexico and Costa Rica.
Panama: The Top Warm-Weather Destination for Winter 2026
Panama is warm and sunny throughout Yeshiva Week, with daytime temperatures in the mid-80s and low humidity compared to the summer. It’s one of the most reliable destinations for winter sun, and even short afternoon showers are part of the charm — they clear quickly and cool things down.
Kosher Food & Minyan
Panama continues to have one of the strongest kosher infrastructures outside Israel and the U.S. Travelers can easily find kosher restaurants and minyanim in Panama through TJT’s directory, with dozens of eateries, bakeries, supermarkets, and shuls concentrated in Panama City. You’ll find everything from fine dining to shawarma, sushi, dairy cafés, steakhouses, and fully stocked kosher grocery aisles. There are multiple daily minyanim across several synagogues, including the large Shevet Achim community, making it incredibly convenient for kosher travelers.
There are multiple daily minyanim across several synagogues, including the large Shevet Achim community, making it incredibly convenient for kosher travelers.
What to Do
- Day trip to the Panama Canal
- Explore the Casco Viejo historic district
- Visit the Biomuseo on the Amador Causeway
- Beach day at Playa Blanca, Coronado, or San Carlos
- Jungle and wildlife tours just outside the city
For something different: explore Bocas del Toro for beaches, water activities, and the new Chabad presence
Panama remains the easiest, warmest, and most kosher-friendly international spot for Winter 2026.
Winter vacation in Panama (Photo: Shutterstock)
Caribbean: Warm Weather, Blue Water & Kosher-Friendly Options
The Caribbean remains one of the most reliable warm-weather choices for Yeshiva Week. With sunshine, turquoise water, and easy flight connections, it’s a favorite for families looking to relax in January and February.
The Caribbean remains one of the most reliable warm-weather choices for Yeshiva Week. With sunshine, turquoise water, and easy flight connections, it’s a favorite for families looking to relax in January and February.
Across the Caribbean — including Aruba, the Bahamas, Puerto Rico, and the Dominican Republic — winter temperatures stay in the upper 70s to mid-80s with low humidity. It’s beach-perfect weather during the exact weeks when the East Coast is freezing.
Kosher Food, Minyanim & Villas
Kosher options vary by island, but many destinations now have Chabad centers, kosher restaurants, packaged meal services, and Shabbat arrangements. For a full overview of kosher dining, minyan availability, and island-specific tips, see our guide to kosher vacations in the Caribbean.
This region is also one of the most popular places for kosher-friendly villa rentals, especially for families who want more privacy, space, and the flexibility to bring in kosher food or arrange catered meals. Islands like Aruba, Jamaica, Puerto Rico, and the Dominican Republic offer a range of villas and resort residences that work well for kosher travelers.
What to Do
- Relax on world-famous beaches with calm, swimmable water
- Snorkeling, catamaran cruises, and water sports
- Explore national parks, caves, waterfalls, and coastal trails
- Visit historic towns and colorful markets
- Resort amenities such as pools, spas, kids clubs, and entertainment
Whether you choose Aruba’s steady breezes, the Bahamas’ turquoise lagoons, Puerto Rico’s mix of culture and nature, or the Dominican Republic’s all-inclusive resorts, the Caribbean offers a warm, easy, and kosher-friendly escape for Winter 2026.
Winter vacation in Miami Beach (Photo: Envato)
Florida: A Classic Yeshiva Week Destination
Florida remains mild, sunny, and comfortable in January and February. Miami, Surfside, Bal Harbour, Boca Raton, and Hollywood are warm enough for the beach, though evenings can get cooler.
Kosher Food & Minyan
Florida continues to be a top choice for kosher travelers thanks to its wide range of restaurants and the convenience of nearby minyanim. From Miami’s upscale dining to Surfside’s bakeries, cafés, and supermarkets, there’s no shortage of options — you can explore more in our guide to kosher and Jewish life in Florida. Daily minyanim are easy to find throughout South Florida, especially in Miami Beach, Surfside, Aventura, Boca Raton, and Hollywood.
What to Do
- Spend the day on Miami Beach or Hollywood Beach
- Visit the Miami Seaquarium, Vizcaya, or Wynwood Walls
- Shopping at Bal Harbour Shops or Aventura Mall
- Water sports, boat rentals, and Everglades tours
Florida remains a classic and comfortable choice — familiar, convenient, and packed with kosher options.
Mexico: Cancun & Playa del Carmen
Mexico is warm and tropical during Yeshiva Week, with temperatures in the low 80s and calm ocean conditions.
Kosher Food & Minyan
Cancun and Playa del Carmen offer several kosher restaurants, kosher grocery products, and strong support from Chabad of Cancun and Chabad of Playa del Carmen. Travelers can find full details in our guide to kosher and Jewish life in Mexico. Many visitors also arrange Shabbat meals through Chabad.
What to Do
- Explore the beaches of Cancun and Playa del Carmen
- Day trips to Cozumel
- Visit Tulum or Chichén Itzá
- Snorkeling and cenote swimming
Winter vacation in Playa del Carmen, Mexico (Photo: Envato)
Costa Rica: Nature, Beaches & Adventure
Costa Rica is in its dry, sunny season during January and February. Expect temperatures in the low-to-mid 80s, ideal for outdoor adventures.
Kosher Food & Minyan
Chabad in San José and Chabad in the Guanacaste region offer kosher meals, groceries, and Shabbat options. Kosher travelers often base themselves in areas like Tamarindo, Jaco, and La Fortuna. For a full overview of kosher food, minyanim, and travel tips, see our kosher vacation guide to Costa Rica.
What to Do
- Ziplining, jungle tours, and wildlife viewing
- Visit Arenal Volcano
- Explore the cloud forests of Monteverde
- Relax on beautiful Pacific beaches
Costa Rica is perfect for travelers who want sunshine and adventure with kosher support nearby.
Conclusion
Yeshiva Week may look different from school to school, but one thing never changes: when the cold sets in, kosher travelers start dreaming of sunshine. What used to be a choice between Florida or staying home has turned into a world of possibilities. From Panama’s incredible kosher infrastructure to the Caribbean’s turquoise water, Mexico’s beaches, and Costa Rica’s adventure-filled landscapes, there are more warm-weather options than ever before — each with reliable kosher food, minyan support, and activities for the whole family.
Whether you want a laid-back beach week, a luxury resort, a private villa, or an active nature escape, Winter 2026 offers something for every type of traveler. With so many kosher-friendly destinations to choose from, planning your Yeshiva Week vacation has never been easier.
Wherever you go, enjoy the sunshine, explore something new, and make the most of the break — warm weather is just a flight away.