Warm Winter Vacations That Make For The Perfect Escape

When you’ve had enough of the cold.

warm winter vacations

Yes, the winter season often brings skiing, snowboarding, snow days, and warm fireplaces. But, what about those who aren’t cut out for the chilly winter temps, or those who can only deal with freezing conditions for so long? Having a warm getaway you can escape to when you just can’t handle the cold anymore is always a great idea. These sunny destinations allow you to soak in some warmth while you wait for spring and summer to come around again.

Luckily, there’s a garden variety of locales to retreat to, and many don’t require you to venture too far. You can go on a quick weekend jaunt to the warm beaches of Florida, or head to other states — like South Carolina or Hawaii — that remain acceptably warm throughout the year. Or — if you’re looking to completely escape any and all temperatures below 50 degrees, jetting to another country that's perpetually sunny (here’s looking at you, Mexico) or whose summer months align with the U.S. winter may be the best move for you. In addition to delivering a much-needed change of scenery and temperature, escaping a wintery environment for even a short amount of time can help those prone to seasonal depression, tacking on some mental health benefits that are truly worthwhile (especially after the holiday season high wears off).

So, if you’re in need of ideas for your next winter getaway, TZR compiled a list of locations to explore. Keep reading for seven travel expert- approved places to can head to this winter to escape the cold.

Cabo San Lucas, Mexico

Travel expert Christina Vidal Haisfield, also known as Jetset Christina, believes Cabo is always a good idea. “With warm weather and easy flights from the U.S., it’s one of my favorite winter escapes.” She loves checking into the Waldorf Astoria Pedregal, where every room has a private plunge pool overlooking the Pacific. “It’s a dream,” she exclaims.

South Africa


“This might be a long journey to get to, but if you’re dreaming of warmth, going to the other side of the Earth that allows you to be in peak summer weather is about as good as it gets,” travel expert Brie Shelly shares. She loves mixing vibrant Cape Town and its beaches with time in the winelands, and of course exploring the beautiful safari.

Palm Beach, Florida


Cofounder of Snob World, a luxury concierge service, Kelsea Moscatel loves going to Palm Beach during the winter months. “It’s always fun to have a contrast between hot and cold during the holidays and Palm Beach is one of the most fun places to do it,” she shares. Whether you’re relaxing at the beach, enjoying a yacht day, or going on a Christmas shopping spree, there are endless activities you can do there without dealing with the cold winter weather.


“A tiny Caribbean island that used to be reserved for private jets and boats only, Anguilla got a lot easier to get to this year when American Airlines added a direct flight from Miami, and everyone needs to go,” Haisfield explains. This idyllic Caribbean gem is full of great food, beautiful beaches, and dreamy hotels. She recommends checking into the Belmond Cap Juluca for the beach, Malliouhana Auberge for the views, or Four Seasons Anguilla for the quintessential Four Seasons treatment.


Haisfield likes to escape to Hawaii because winter not only means perpetual sunny tropical weather, but also whale watching season. “The humpback whales swim more than 3,000 miles from the Gulf of Alaska down to Hawaii chasing warmer waters for their own vacation from December through May,” she shares. Spend your days sipping mai tais, watching whales, snorkeling with turtles, visiting the volcanoes national park, waterfall-chasing on the road to Hana, golfing, or just soaking up the Hawaiian sun,” she explains. Her top picks for where to stay are the Four Seasons Wailea in Maui and the Four Seasons Hualalai on the Big Island.

Costa Rica

Shelly says traveling to Costa Rica will allow you to completely forget about the cold winter weather. Heading to a spot where you can mix culture, rainforest adventures, and the beach all into one country is ideal for anyone in need for a winter escape. “You can go for a few days to do one of these or stay for a week and mix and match,” she explains. It’s a great place anyone who despises cold weather will thoroughly enjoy. Pro tip: Stay at the Four Seasons Resort at Peninsula Papagyo which overlooks the ocean, and enjoy the spa, pool and amazing food it offers.

Charleston, South Carolina

Charleston’s mild winter makes it an ideal getaway in the U.S. “While you won't get the warm weather of Florida, you’ll get a cozy coastal getaway full of great food, great shopping, beautiful boutique hotels, and one-of-a-kind Southern hospitality,” Haisfield shares. She suggests checking out a few of her favorite restaurants while you’re there. “I love Chubby Fish, Vern’s, Sullivan’s Fish Camp, 82 Queen, and a little romantic hidden Spanish tapas gem called Malagon.”