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Winter in Miami is a special time, but not necessarily because of the weather. Temps barely change unless a two-day cold front sneaks in and sends the entire city into Ugg hysteria.
The magic is in the travel deals. While the rest of the country digs cars out of snowbanks, South Floridians can pop over to MIA (or FLL, or maybe even PBI) and get to a different beach or the Northern Lights in no time. This winter’s flight sales are especially enticing. Think double-digit tickets to the Caribbean, under-two-hour domestic hops, and international fares that look like someone typed them wrong altogether. Alphabetized for your scrolling pleasure, here are the ten best winter getaways from Miami to book before the fares thaw.
Bradenton Area Tourism Bureau photo
Bradenton, Florida
A new American Airlines nonstop route from MIA means you can trade Miami traffic for Bradenton and Anna Maria Island’s sugar-sand in just over an hour. Round-trips often dip under $200 for Old Florida charm: pastel cottages, turquoise water, and seafood straight off the docks of Cortez, the state’s oldest fishing village. Winter brings the Manatee River Holiday Boat Parade and the European Holiday Market, making the Gulf Coast feel delightfully festive without requiring a five-hour drive.
Charleston, South Carolina
With round-trip flights that can run you less than $100 and span under two hours, Charleston is one of the cheapest, quickest winter swaps for Miami sunshine. The Beach Club at Charleston Harbor Resort & Marina delivers waterfront views, firepits, and the returning Winter Wonderland festival through January. Think cozy gondola rides and the only outdoor, eco-friendly ice-skating in the city. The Charleston Place is a stellar option, too, with five-star accommodations, a central location, and an on-site Holiday Train.
Iceland
Yes, Iceland. Round-trip fares from Miami have been shockingly reasonable this season, and winter is prime time for Northern Lights hunting. Station yourself at Hotel Rangá on the South Coast and let the skies do the work; you can literally see auroras without leaving the property. By day, it’s all about snowmobiling atop glaciers, trekking into blue ice caves, and checking out the new geothermal lagoon just 45 minutes from the hotel.
Photo by Jesse Scott
Key West, Florida
With Spirit’s new flight from Fort Lauderdale to Key West, winter in the Conch Republic has never been easier — or cheaper. Fares frequently hover in the low triple digits, and once you’re wheels-down, all the classics await: Sebago Watersports snorkeling outings, nights playing yard games at The Backyard Pool & Social Club at Blue Flamingo Resort, or belting questionable notes at the best karaoke place on Earth, EmPourium.
Nassau, Bahamas
Multiple nonstop flights for under $250 make Nassau the ultimate “Why am I still at my desk?” winter escape. It’s less than a one-hour flight away, but the Bahamian sunshine hits differently this time of year. Margaritaville Beach Resort Nassau sweetens the season with its ’Tis the SeaSon offer, which donates $5 per night to Ranfurly Homes for Children and rewards guests with 20 percent off rates plus resort credits.
Providenciales, Turks and Caicos
About ninety minutes from Miami and often under $300 round-trip, Provo is the Caribbean easy button. For seclusion, Rock House serves cliffside views, a private white-sand cove, and the largest infinity pool on the island. For something more sprawling, South Bank offers waterfront villas, a man-made swimming lagoon, a chic beachfront, and enough boating access to make even the most casual Miamian consider purchasing deck shoes.
Puerto Rico
Double-digit Spirit fares to San Juan? Yes. A passport required? Absolutely not. Puerto Rico remains an easy warm-weather getaway for South Floridians, and winter is prime time thanks to the island’s famously long holiday season. The newly transformed Wyndham Grand Rio Mar debuts this month with rainforest-immersive wellness, stargazing sessions, river kayaking, a vintage-themed casino, and a speakeasy cabaret. In San Juan, make sure to pop into Mar y Rosa, the stunning new rooftop gem from Jose Mendin (of Pubbelly Sushi fame) with sweeping Old San Juan vistas and killer cocktails.
Puerto Vallarta Tourism Board photo
Puerto Vallarta, Mexico
With round-trips dipping into the $300s and sometimes below, Puerto Vallarta is one of the best-value winter escapes on the Pacific. The mountains, jungle, cobblestone streets, and historic districts offer a wildly different pace from Miami. Winter is peak whale-watching season and home to the long-running ArtWalk, which stretches from November through June. Dry season weather seals the deal: sunny, breezy, and tailor-made for beach days bookended by mezcal.
Punta Cana, Dominican Republic
Miami to Punta Cana remains one of the cheapest Caribbean links all winter, with frequent sales and multiple carriers keeping fares friendly. Once there, elevate the trip with a stay at Eden Roc Cap Cana, where suites feel like mini sanctuaries, the beach looks like a screensaver, and the area’s dining continues to level up. Winter also brings calmer seas and prime conditions for snorkeling and sailing. Even better, nothing here requires fighting resort-town crowds like it’s spring break 2009.
Sint Maarten
Three hours from Miami and consistently affordable, Sint Maarten is an easy winter stopover. The island’s mix of French and Dutch cultures means one moment you’re devouring pastries, and the next you’re beach-hopping or watching planes skim Maho Beach. For luxury seekers, the JW Marriott St. Maarten delivers five-star comfort without five-star flight costs. Winter here means endless sunshine, and the area’s nickname, the Friendly Island, is no marketing gimmick.
