Every winter, I find myself itching for sun – but not for sky-high airfare or packed resorts. Over the years, I’ve learned that the best winter escapes aren’t necessarily the most obvious ones. Some of the best trips I’ve taken started with a cheap flight alert and a little flexibility.
If you’re wondering where to travel this winter for cheap flights and sunshine, this list is for you. These spots offer warm weather, solid flight deals, and a sense of escape that doesn’t require months of planning or a five-figure budget. A few are tropical, others more cultural, but each one is realistic, refreshing, and very doable…even in the heart of winter.
- ✈️ Pro tip: Want winter flight deals sent straight to your inbox? Sign up for Going (there’s a free version!) to get alerts when fares drop on your favorite routes. Going’s a membership-based service that finds huge discounts, mistake fares, and points-and-miles deals. Free accounts are great for domestic deals, while Going Premium unlocks international winter getaways for up to 90% off.
Below are my top winter destinations in 2026 with cheap flights, great weather, and easy itineraries, from Caribbean beaches to fun city breaks.
1. Cartagena, Colombia
- ✈️ Flight Price Range: $150–$300 roundtrip
- 🏖️ Beach Access: Rosario Islands day trips, Playa Blanca, or stay beachside in nearby Bocagrande
- 🔄 Top Airline Deals: Copa, Avianca, JetBlue
Colorful, coastal, and incredibly affordable, Cartagena is one of the easiest winter warm-ups if you’re flying from the US. January through March is the sweet spot: dry, breezy, and reliably sunny, with daytime temps hovering in the low-to-mid 80s. That makes it perfect for everything from old town strolls to Rosario Island day trips.
Once you land, the value keeps coming. You can walk the entire walled city, catch live music in leafy plazas, and fill up on street arepas and fresh juices for a few bucks. I recommend staying inside the Ciudad Amurallada for the full colonial charm. Yes, it’s slightly pricier than the modern beach strip, but it’s 100% worth it for the vibe and walkability.
If Cartagena isn’t affordable on your preferred travel dates, check out Santa Marta or Medellin instead. Last winter, I spent two weeks masterminding in both places with one of my good friends. I find Colombia to be the perfect winter reset with great prices, great weather, and some of the freshest food around!
✈️ My Pro Tip: I’ve seen solid roundtrip deals on Going that make this escape totally doable, like a recent $248 fare from Orlando, 58% off the usual rate.
2. San Juan, Puerto Rico
- ✈️ Flight Price Range: $180–$320 roundtrip
- 🇺🇸 No Passport Needed: US territory means no international hassles, plus your phone works normally
- 🌴 Winter Weather: 80°F days, gentle trade winds, and way less rain than summer months
San Juan might be the smartest winter escape that nobody thinks of. You get Caribbean warmth and colonial charm without dealing with customs, currency exchange, or roaming charges.
December through April brings the island’s best weather – sunny, breezy, and comfortable enough for both beach days and exploring Old San Juan’s cobblestone streets.
The mix here is unbeatable. Enjoy UNESCO-listed forts, incredible food (mofongo, fresh seafood, craft cocktails), and beaches that are a quick Uber ride from the airport. Stay in Condado or Isla Verde if you want beachfront convenience, or pick Old San Juan for maximum character and walkability. I also loved visiting Ponce in the south, which has more affordable hotels. Either way, you’re looking at way better value than most Caribbean islands.
Winter is also when the local food scene really shines. Fewer cruise ship crowds mean you can actually get tables at the best spots, and the weather’s perfect for rooftop bars and outdoor dining.
✈️ Pro Tip: I’ve found the best deals to Puerto Rico come from East Coast cities. Boston, New York, and Miami consistently see sub-$200 fares on Going when you’re looking for where to fly in winter for great weather.
3. Punta Cana, Dominican Republic
- ✈️ Flight Price Range: $200–$380 roundtrip
- 🏖️ Beach Paradise: 20+ miles of white sand beaches with calm, swimmable waters year-round
- 🔄 Top Airline Deals: Arajet, JetBlue, American
Punta Cana gets a lot of resort attention, and honestly, it earns it. But beyond the all-inclusive scene, there’s plenty of character if you know where to look. I recently spotted a $240 roundtrip deal from Chicago on Going, and it reminded me how easy it can be to swap winter gray for Caribbean blue without blowing your budget.
Winter here means consistent 82°F weather, minimal rain, and some of the Caribbean’s most reliable beach conditions. The water stays warm and calm, perfect for both lazy floating and actual swimming.
My go-to area is Macao, about 30 minutes from the main hotel strip. It’s laid-back, locally loved, and you’ll still find stretches of beach with barely a soul around. Great for watching surfers at golden hour with an ice-cold Presidente in hand.
If you’re after something smaller than the mega-resorts but still elevated, I highly recommend Tortuga Bay at Puntacana Resort & Club. It’s located inside a quiet, palm-lined enclave and gives you beachfront access with a lot more breathing room. Still close to great food and coastal towns like El Cortecito, but without the crowds.
Even if you’re not into full resort mode, there are gems to be found all along this coast – and winter is the best time to do it without the summer humidity.
✈️ Pro Tip: Head inland to Montaña Redonda for one of the best panoramic views in the country. It’s a hilltop with giant swings overlooking the jungle and sea – surreal at sunrise, and way less touristy than you’d expect.
4. Oranjestad, Aruba
- ✈️ Flight Price Range: $195–$350 roundtrip
- 🌵 Guaranteed Sun: Outside the hurricane belt with 82°F temps and less than 20 inches of rain annually
- 🔄 Top Airline Deals: JetBlue, American, Delta
Aruba lives up to its nickname – “One Happy Island” – especially when you’re flying in from somewhere frozen. From December to March, the forecast here barely budges: blue skies, 80-something degrees, and trade winds that make it feel like a warm hug instead of a sweat-fest. If you want reliable winter beach weather, this is it.
Oranjestad, the capital, is colorful and compact, great for wandering between Dutch-colonial buildings, local snack shacks, and harbor views. You don’t need to rent a car if you stay central. The downtown streetcar is free, and local buses can get you to Eagle Beach or Palm Beach in under 20 minutes.
For something a little different, I always recommend heading south to Mangel Halto. It’s a quiet, mangrove-fringed cove with clear water, perfect for snorkeling without the crowds. There’s a local beach bar nearby, and it feels miles away from the polished resort zone.
✈️ Pro Tip: Aruba’s tap water is some of the cleanest in the world! Skip the plastic bottles and drink straight from the faucet.
5. West Palm Beach, Florida
- ✈️ Flight Price Range: $78–$200 roundtrip
- ☀️ Winter Sun: December through March brings steady 75–80°F days, low humidity, and ocean temps warm enough for a dip.
- 🔄 Top Airline Deals: Breeze, JetBlue, Southwest
Trust me when I say that West Palm Beach is Florida’s best-kept winter secret. It’s warm, breezy, and walkable – plus it feels like the best of Miami and a beach town rolled into one. I spotted a $78 roundtrip fare from New Haven to West Palm Beach for this December on Going. It’s hard to argue with palm trees and rooftop cocktails for less than the price of a dinner out!
The mix here works perfectly for a winter escape. You’ve got stunning beaches (Palm Beach is gorgeous and way less crowded than anything further south), plus Clematis Street downtown for good restaurants and bars that don’t feel touristy. I love staying near the Intracoastal. You get water views, walkable neighborhoods, and easy access to both the beach and the surprisingly good food scene.
If you’re up for a little exploring, rent a bike and head south toward Lake Worth or north to Juno Beach. Both are less crowded than the downtown stretch, and equally sun-soaked.
If flight options are limited, you can always fly to nearby airports in Miami or Fort Lauderdale. But trust me, you don’t want to pass up on West Palm Beach…it’s definitely worth the visit.
✈️ Pro Tip: Head to Grato during happy hour for wood-fired pizza, half-priced wine, and a patio that feels like it was made for mid-70s weather and zero plans.
6. Tulum, Mexico
- ✈️ Flight Price Range: $261–$420 roundtrip
- 🏛️ Mayan Ruins: Ancient clifftop temples overlooking turquoise Caribbean waters
- 🔄 Top Airline Deals: American, United, Volaris
If you’re wondering where to fly for winter sun from the US, that’s easy, beautiful, and not wildly expensive, Tulum’s still got it. Yes, it’s grown into a full-blown hotspot, but believe me – there’s more to the story than beachfront DJs and smoothie bowls.
The weather is exactly what you want in winter: sunny, mid-80s, and dry. Head to the quieter beaches south of the hotel zone (Playa Xcacel or the sands near the Sian Ka’an Biosphere) and you’ll forget you’re near one of Mexico’s buzziest towns. Inland, spots like Cenote Escondido and Casa Tortuga offer crystal-clear water and shaded swimming without the Instagram crowds.
If you stay in town (Tulum Pueblo), you’ll find taquerias, cheap bike rentals, and boutique hostels that still feel connected to the local community. Plus, it’s way more budget-friendly than the beach strip.
✈️ Pro Tip: Tulum opened its own airport in late 2023, but if direct flights are pricey, fly into Cancún instead and take the 90-minute shuttle for around $15-25. You can also fly into Cozumel and take the ferry to Playa del Carmen, then bus to Tulum. Sometimes this routing saves $100+ per ticket.
7. Casablanca, Morocco
- ✈️ Flight Price Range: $392–$550 roundtrip
- 🌡️ Perfect Winter Climate: Mid-60s and mild on the coast, perfect for exploring cities, souks, and mountain routes without the summer heat.
- 🔄 Top Airline Deals: TAP Air Portugal, Royal Air Maroc, Lufthansa
If you’re looking for a winter escape and a serious change of scenery, Casablanca is one of the smartest ways to unlock Morocco. Going recently flagged a $392 roundtrip from Newark, which honestly blew my mind. That’s a coast-to-coast cultural reset for less than a weekend in NYC!
The weather’s ideal for travelers: highs in the 60s, dry skies, and just enough breeze to make tea in a tiled courtyard feel cinematic. Unlike Marrakech or Fez, Casablanca isn’t built for tourists. It’s a modern coastal city with palm-lined boulevards, French-influenced architecture, and a busy port scene where you can dive into real-deal Moroccan seafood before you’ve even unpacked.
But here’s the real value: location. From Casablanca, you can hit the beaches of Agadir or Essaouira, ride the train to Marrakech in under 3 hours, or head inland toward the Atlas Mountains for winter hikes with snow-dusted peaks and crisp mountain air. It’s a launchpad for one of the most diverse and beautiful countries you can reach on a sub-$400 ticket.
✈️ Pro Tip: Learn a few basic French phrases before you go. While Arabic is the official language, French is widely spoken and opens doors to better conversations, especially with older locals who grew up during the French protectorate era.
8. Puerto Vallarta, Mexico
- ✈️ Flight Price Range: $198–$420 roundtrip
- 🌮 Authentic Mexico: Real Mexican culture beyond the resort zone, plus incredible street food scene
- 🔄 Top Airline Deals: American, Southwest, United
Puerto Vallarta hits the sweet spot between authentic Mexican charm and winter beach perfection. While Cancun feels like spring break central, PV maintains its fishing village soul even as it’s grown into a proper city. December through March brings perfect 80 degree days, minimal rain, and ocean temps that feel refreshing instead of bathtub warm.
What I love about PV is how layered it is. You’ve got the postcard pretty Malecón waterfront for sunset strolls, but also the real neighborhoods up in the hills where families have lived for generations.
Skip the resort strips and head to Zona Romántica for walkable streets, local galleries, and restaurants where you’ll hear more Spanish than English. The food scene here rivals anywhere in Mexico, from $2 street tacos to world class fine dining.
The surrounding area gives you serious adventure options, too. Take day trips to hidden beaches like Yelapa (accessible only by boat), explore the mountain towns like San Sebastián del Oeste, or just post up at one of the beach clubs in nearby Sayulita for a more bohemian vibe.
✈️ Pro Tip: I spotted a $278 roundtrip deal from Denver with a return layover in Phoenix, and it was still half the usual price. If you’re a Going Premium member, you’ll get international deals like this all the time, often to places you didn’t realize were this close.
9. Long Beach, California
- ✈️ Flight Price Range: $90–$280 roundtrip
- ☀️ Winter Sun: Mid-70s and sunny with ocean breezes and zero need for snow boots.
- 🔄 Top Airline Deals: Southwest, Alaska, JetBlue
Southern California in winter just hits different. While the rest of the country’s layering up, Long Beach stays mellow and mild, with highs in the 70s, golden light on the water, and beach days that actually feel like beach days.
It’s less flashy than LA, but that’s why I love it. Long Beach has a laid-back, locals-first vibe that makes it feel instantly comfortable. You’ve got quiet stretches of sand, bikes along the boardwalk, the incredible food scene in Retro Row, and boat rides through Naples Island’s canals that feel more Venetian than Californian. Plus, it’s a great base. Long Beach is close to Catalina Island, under an hour to Joshua Tree, and just far enough from the LA chaos to breathe. I spotted a $144 roundtrip fare from Seattle on Going that makes this kind of escape feel easy. No long-haul flights, no snow, no stress.
✈️ Pro Tip: Rent an e-bike and cruise the Shoreline Trail in the afternoon. Stop at Saltwater Deck for fish tacos and a local craft beer, then catch the sunset from Bluff Park. It’s peak winter peace, California-style.
10. San Jose, Costa Rica
- ✈️ Flight Price Range: $256–$380 roundtrip
- 🌿 Adventure Gateway: Central location for beaches, volcanoes, cloud forests, and wildlife reserves
- 🔄 Top Airline Deals: United, American, Southwest
I love Costa Rica. San José gets overlooked as just a stopover city, but smart travelers use it as their base camp for exploring Costa Rica during dry season. January through March delivers a perfect combination of sunny skies, comfortable temperatures, and minimal rainfall that makes every outdoor adventure actually enjoyable – instead of a sweaty slog!
The real genius of staying in or near the capital is proximity to everything Costa Rica does best. You can wake up in the city, drive two hours to watch the sunrise over Arenal Volcano, then finish the day soaking in natural hot springs. Or, head the opposite direction to Manuel Antonio for beach time and sloth spotting. The whole country feels manageable when you’re centrally located.
San José itself has grown on me over multiple visits. The coffee is excellent, the local markets are full of character (and hot sauce), and it’s a much more affordable stop than the coast. Spend a night or two, get your bearings, then head out into the green.
✈️ My Pro Tip: I spotted a $256 roundtrip deal from DC to San José using Going Premium, which tracks international economy deals all over the world. If you’re wondering where to travel in winter for cheap flights and sunshine, Costa Rica is one of the most rewarding picks on the map.
Looking to travel internationally in 2026? Use my discount code JON25 to save 25% on Going’s Premium Version.
