Warm winter getaways from San Juan
Escape the cold: sunny places you can fly to from San Juan from November through March, from Caribbean beaches to summer in the southern hemisphere, each with the cheapest round trip we've seen recently for those months.
Saved round trips, entirely within Nov, Dec, Jan, Feb, Mar.
Cheapest right now: Miami $112 · Fort Lauderdale $207 · Punta Cana $261
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Fares observed October 2 – 8, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from San Juan
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | $413 (airline $436) | Feb 1–Mar 3, 2027 | Check prices |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | $261 (airline $275) | Mar 13–20, 2027 | Check prices |
| Aruba (AUA) | Dry, sunny and outside the hurricane belt, so it is a safe bet most of the year | $661 (airline $697) | Nov 24–29, 2026 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | $398 (airline $419) | Mar 13–20, 2027 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | $503 (airline $530) | Jan 15–18, 2027 | Check prices |
| Puerto Vallarta (PVR) | Puerto Vallarta's Pacific beaches and a walkable old town | $617 (airline $649) | Feb 1–Mar 3, 2027 | Check prices |
| Los Cabos (SJD) | Los Cabos, desert coast, resorts and whale watching in winter | $933 (airline $986) | Jan 4–Feb 2, 2027 | Check prices |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | $517 (airline $547) | Feb 1–Mar 3, 2027 | Check prices |
| Panama City (PTY) | Panama City's skyline and the canal, warm all year | $497 (airline $526) | Jan 4–Feb 2, 2027 | Check prices |
| Cartagena (CTG) | Cartagena's walled old town and Caribbean islands nearby | No matching fare saved | Search other dates | |
| Medellin (MDE) | Medellín, known as the city of eternal spring | $293 (airline $308) | Mar 1–30, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | $1,045 (airline $1,101) | Jan 4–Feb 2, 2027 | Check prices |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | $829 (airline $876) | Feb 12–15, 2027 | Check prices |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | $112 (airline $118) | Dec 3–7, 2026 | Check prices |
| Fort Lauderdale (FLL) | Fort Lauderdale beaches and an easy base for cruises | $207 (airline $219) | Jan 15–18, 2027 | Check prices |
| Tampa (TPA) | Gulf beaches at Clearwater and St. Pete | $288 (airline $304) | Mar 11–16, 2027 | Check prices |
| Fort Myers (RSW) | Fort Myers and Sanibel on Florida's Gulf coast | $356 (airline $375) | Dec 22–29, 2026 | Check prices |
| Phoenix (PHX) | Phoenix and Scottsdale, warm and sunny all winter | $503 (airline $530) | Jan 15–18, 2027 | Check prices |
| Palm Springs (PSP) | Palm Springs, desert sun, pools and mid-century style | $413 (airline $437) | Feb 1–Mar 3, 2027 | Check prices |
| Tucson (TUS) | Tucson's desert, mountains and winter sunshine | No matching fare saved | Search other dates | |
| San Diego (SAN) | San Diego's beaches and mild weather all year | $307 (airline $324) | Feb 12–15, 2027 | Check prices |
| Rio De Janeiro (GIG) | Rio de Janeiro, where it is summer when it is winter in the US | $829 (airline $876) | Feb 4–10, 2027 | Check prices |
| Buenos Aires (EZE) | Buenos Aires, in its summer during the US winter | $1,620 (airline $1,710) | Dec 18, 2026–Jan 3, 2027 | Check prices |
| Cape Town (CPT) | Cape Town's beaches, mountains and wine country in its summer | $3,973 (airline $4,198) | Dec 18, 2026–Jan 3, 2027 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
Hotels in Cancun with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Warm winter getaways from San Juan. Where to fly from San Juan for sun in winter: beaches, deserts and summer in the southern hemisphere, with real round-trip fares.
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