Six warm trips, side by side
January and February are when a warm week matters most, and when the right place depends on how far you can fly and whether every child has a passport. Average highs below come from our own weather data. Flight times are approximate, from our flight dataset, so check the live schedule, including whether your route is nonstop.
| Destination | Jan / Feb high | Approx. flight: LAX / ORD / JFK | US passport | Best for |
|---|---|---|---|---|
| Riviera Maya | 82°F / 83°F | 4h30 / 3h15 / 3h45 | Yes | All-round beach week |
| Puerto Rico | 83°F / 84°F | 7h30 with a connection / 4h15 / 3h30 | No | Warm water, no passport |
| Maui | 81°F / 81°F | 5h50 / 9h30 with a connection / 11h with a connection | No | Whale season |
| Los Cabos | 77°F / 79°F | 2h35 / 5h / 6h30 with a connection | Yes | Quick dry escape from the West Coast |
| Guanacaste, Costa Rica | 92°F / 93°F | 6h / 5h / 5h30 | Yes | Heat and sun, older kids |
| Orlando | 72°F / 74°F | 4h55 / 2h45 / 2h45 | No | Theme parks in mild weather |
Plan around the two Monday holidays
Two federal holidays fall in this window in 2027: Martin Luther King Jr. Day on January 18 and Washington’s Birthday on February 15. They are the long weekends most families reach for, and some school districts add a winter break around the February date. If your calendar allows it, price a week away from those Mondays before you settle on a destination, and if it does not, book those weeks first.
The six trips
Riviera Maya: the all-round beach week
Our data has highs of 82°F to 83°F, warm enough for real beach days without Guanacaste’s heat. All-inclusive resorts also make the budget simple. Grand Palladium Kantenah has baby, mini and junior clubs and a children’s water park. The catch is the transfer: the resort says it is about 90 minutes from Cancún airport, which is a long last leg with small children.
Puerto Rico: warm water without a passport
Puerto Rico’s tourism board confirms US citizens don’t need a passport, which makes it the easy choice when a child’s passport is pending. Highs run 83°F to 84°F. It is an easy flight from the East Coast and a long one from the West. El Conquistador in Fajardo has a water park with a lazy river and its own beach island; the slides need riders 48 inches or taller, and no kids’ club is listed.
Maui: the whale-season week
NOAA’s humpback whale sanctuary says humpbacks are generally seen in Hawaii from November through April, with the peak from January through March. Highs hold at 81°F, and winter surf changes which beaches suit small children. Our Hawaiian island guide covers which shores to pick. The Hyatt Regency Maui has a children’s splash pad, slides and daily penguin presentations, so a slow morning still works.
Los Cabos: the quick dry escape from the West Coast
About 2h35 from LAX, on a desert coast, with highs of 77°F to 79°F. Evenings are cool, with lows near 58°F, and so is the ocean, so plan on pool days and pack layers. In winter it sits just one hour ahead of Los Angeles; our short international flights from LAX guide explains why that matters. Hyatt Ziva Los Cabos has a mini water park with five slides, a toddler splash pool and a kids’ club for ages 4 to 12, but the beach in front is not on the tourism board’s swimmable list.
Guanacaste, Costa Rica: the hot, dry week
Our data puts January and February at 92°F to 93°F, the hottest stop here, and it is the dry season. That suits older kids who want sun and activity; with a baby or toddler, plan around the midday heat. Westin Reserva Conchal is an all-inclusive with a lagoon-style pool and a kids’ pool. It does not publish its kids’ club ages, so ask before booking.
Orlando: theme parks in mild weather
Highs of 72°F to 74°F are comfortable for long park days, but lows near 52°F mean jackets at rope drop, and a pool day is not a given. Laughing Place reports Disney’s EPCOT International Festival of the Arts running from January 15 through March 1 in 2027. At Universal, Cabana Bay has family suites that sleep six and a lazy river. See our best time to go to Disney World guide before picking a week.
Which one, by age
- Baby or toddler: Puerto Rico from the East Coast or Los Cabos from the West, for the shorter travel day. Riviera Maya if a baby club matters more than the transfer.
- Ages 4 to 8: Orlando if parks are the point; Riviera Maya or Los Cabos if a kids’ club and a pool are.
- Tweens and teens: Maui for whales, or Guanacaste for heat and sun.
These are our reading of the data above, not the result of testing each trip. Want snow instead? Start with our family ski resorts guide. Planning further ahead? See spring break destinations for families. Staying home this winter? Make a winter bucket list for the family instead.
Passports take longer than the flight
Mexico and Costa Rica are international flights, and US Customs and Border Protection says children must present their own passport when traveling by air. No lap-child exemption applies. If a passport will not arrive in time, Puerto Rico, Maui and Orlando keep the trip alive. Our kids’ travel documents guide covers the rules and timing.
Rates: Booking.com · Excursions: Viator (ages and cancellation terms listed per tour)



