8 Warm-Weather Winter Getaways in America

Cliché as it may be to say, winter is coming. That is, winter is coming unless you live in one of those rare destinations where winter never actually comes. And yes, I am that guy who lives in one of those destinations, Los Angeles. But it’s actually those warm-weather destinations, like Los Angeles, that make the best winter getaways. So you’re welcome!

 With many winter destinations starting to see their first snowfalls, I thought it was high time to write about some of my favorite winter getaways that feel like spring (or summer, in some cases). These are all winter-tested, and you’re likely to find me at one (or many more) of these spring-like winter getaways in the coming months. So below, see eight of my favorite warm-weather winter getaways in the U.S.

Joshua Tree

I know I probably say this about a lot of places, but Joshua Tree really is one of my favorite corners of America. While it’s no Positano, Maldives, or Patagonia, Joshua Tree is one of the most unique, quirky, charming, dramatic places I’ve traveled to. And in the winter, it’s also one of the warmest. In fact, don’t bother going in the summer (trust me), but only go in the cooler months. I actually went last year for my birthday, in mid-February, and wore shorts and t-shirts every day.

 Can’t-miss Joshua Tree recommendations:

  • Get in on that national park annual pass action for Joshua Tree National Park, and don’t miss Skull Rock, Ryan Mountain Trail and Cholla Cactus Garden.

  • Go to the Saturday morning Joshua Tree Ceritified Farmers Market, and grab a sandwich and coffee at Natural Sisters Café.

  • Book a reservation weeks, if not months, in advance, at one of my favorite bars in the world, Pappy + Harriet's.

  • Book a unique stay, such as at Hicksville Trailer Palace, as Joshua Tree has some of California’s most unique vacation rentals.

  • Take a sound bath (no, seriously).

joshua tree stargazing

Gulf Shores

I’ve been going to the Alabama Gulf Coast for a few years, riding off the coattails of my sister, who vacations there regularly with her family in the fall. Here’s why I love it: It’s warm and there’s few people there. Honestly, what else do you want? Even better, the seafood is as fresh as you can get. My family often goes in early October, when it’s often still in the 80s, and while it won’t be that warm during the winter months, it’s still pleasant. Plus, it’s far cheaper than any West Coast beach vacation you could have.

 Can’t-miss Gulf Shores recommendations:

  • Grab craft brews at Big Beach Brewing, which is as good of a craft brewery as you’ll find along the coast here.

  • Go for a sunset kayak.

  • Eat fresh seafood. Believe me, you won’t have trouble finding it.

  • See sea turtles at Bon Secour National Wildlife Refuge. 

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Austin is hands down one of my favorite cities in America. I’d consider living there if it wasn’t 1,000% humidity during the summer. During the cooler months, Austin is even better, as you can actually spend all day outdoors without the worry of fainting. It won’t quite feel like summer, but like Joshua Tree and Gulf Shores, you can expect spring-like temperatures. Do a BBQ crawl, hop around Rainey Street’s bars, visit some live music venues, and rent a kayak or SUP to paddle through Austin.

 Can’t-miss Austin recommendations:

  • Take a moonlight, or bat-watching (yes, seriously), cruise through Austin.

  • Eat your way around Austin’s best barbecue restaurants. While Franklin’s is considered the best, the line is outrageous, so I’d alternatively recommend La Barbecue, Micklethwait and Terry Black’s.

  • Go on a craft beer crawl, visting breweries like Hops and Grain or Black Star Co-op.

  • Visit The Picnic, one of Austin’s best food truck parks.

  • Take a day trip to nearby destinations like Hamilton Pool Preserve, or to Driftwood to visit The Salt Lick.

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Scottsdale is actually an annual trip I now do at the end of every winter for Spring Training, which takes places throughout the Phoenix area from mid-February through March. This trip to Scottsdale is one of my favorite all-time road trips, in part for Scottsdale, but also for the experience of Spring Training, which I think is one of the coolest (and cheapest) pro sports experiences you can travel to. Bonus points: It’s shorts weather every day. Even in December and January the temperature is usually in the upper 60s. What I probably love most about Scottsdale, however, is the contrast of experiences, like hiking Camelback Mountain one moment, and the next exploring the great food and drink scene of Old Town Scottsdale.

 Can’t-miss Scottsdale recommendations:

  • Take a hike at Phoenix Mountains Preserve.

  • Eat and drink your way around Old Town Scottsdale, but whatever you do, don’t miss one of my favorite all-time saloons, the Rusty Spur Saloon.

  • Go on an off-roading adventure, offered by a number of different Scottsdale tour companies.

  • Stay at one of Scottsdale’s cool hotels. While I often love staying at vacation rentals, Scottsdale is one of my favorite towns for hotels that are destinations in and of themselves, like The Scott, Fairmont Princess, Royal Palms Resort and Spa, and The Saguaro.

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San Diego

Honestly, there’s not a bad time of year in San Diego, not the least of which during the winter months, when it’s usually in the upper 60s. A given winter day in San Diego could include surfing in the morning, a brewery tour in the afternoon and a sunset hike before dinner. While San Diego is known for breweries, you could also go wine tasting in North County in Escondido, which has a number of tasting rooms and wineries. Or, if you’re looking for an urban getaway, then stay in the Gaslamp Quarter. Otherwise I recommend choosing one of the beach cities, like La Jolla.

Can’t-miss San Diego recommendations:

  • Take a half-day trip to Coronado, a charming beach town located just across the bay from downtown San Diego.

  • While there are so many San Diego breweries to choose from, if you want a one-of-a-kind brewery tour, then check out Scavengers, which does brewery tours in an open-air, vintage Swiss Pinzgauer military vehicle.

  • Spend the afternoon in the 1,200-acre Balboa Park, the largest urban cultural park in North America, and which is home to 17 museums, botanical gardens and more.

  • Paddle the La Jolla Caves. Keep your eyes peeled for unique marine life, including sea lions, seals and leopard sharks.

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New Orleans

I have a confession to make: New Orleans is my favorite city to visit in America. While I could never live there (because summer, and humidity), I think New Orleans is one of the most unique, culturally diverse cities in America, and one of my favorite food and drink destinations. And that’s without even mentioning New Year’s Eve, or Mardi Gras, which takes place in February or March. Hop on the St. Charles Streetcar line, take a gondola ride through City Park (yes, really), go on a bayou tour, and visit some of my favorite cocktail bars in the world, like Cure or French 75.

Can’t-miss New Orleans recommendations:

  • Visit Lafitte's Blacksmith Shop Bar, considered the oldest bar in America.

  • Take a brewery tour of Abita, a 32-year-old brewery that brews its beer with water from artesian wells.

  • Go on a swamp and bayou tour (where else can you take a swamp tour?!).

  • Do a self-guided foodie tour, visiting iconic places like Commander's Palace, Cochon Butcher, Cafe du Mond, Central Grocery, and Liuzza's.

  • Visit The National WWII Museum, ranked on TripAdvisor as one of the top museums in the world.

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Hawaii Island

Hawaii is basically just one endless summer. But where you vacation in part depends on what you want, whether it’s a little urban life on Oahu, a little bit of everything on Maui or Jurassic Park on Kauai. However, I recommend Hawaii Island for a number of reasons. For starters, it’s a great island, which can sometimes get overlooked because of Oahu and Maui. But I especially think now is a great time to visit Hawaii Island to support tourism of a destination that’s had a rough go recently because of a volcanic eruption, flooding and other weather events. So go support a great Hawaiian island, hike a volcano (inactive volcano), visit a black sand beach, eat a plate lunch, and live your best life.

Can’t-miss Hawaii Island recommendations:

  • Go to the top of the 13,000-foot Mauna Kea for sunset and stargazing.

  • Take a lava and waterfall helicopter tour with Blue Hawaiian.

  • Visit Punaluu Black Sand Beach.

  • Pick up a dozen malasadas (you’ll thank me later).

  • Spend a day at Hawaii Volcanoes National Park.

Sunset Mauna Kea summit Big Island.jpg

Florida Keys

You could pick just about any place in Florida that’ll feel like summer year-round, but I like the Florida Keys because it feels as close to an international tropical vacation as you’ll get in the lower 48. That, plus it’s the best of both worlds, as you can combine a tropical Florida Keys getaway with an urban Miami getaway. But while many people vacation in the Lower Keys in Key West, I actually prefer the Upper or Middle Keys, such as Islamorada or Marathon. Along this stretch, you have all the perks of the Florida Keys, like crystal-clear waters, beautiful white sandy beaches, world-class diving, and great local restaurants, but without the bustle of Key West.

 Can’t-miss Florida Keys recommendations:

  • Go at least snorkeling, if not scuba diving, too, since the Florida Keys is one of the best diving destinations in America.

  • Take a boat or seaplane trip out to Dry Tortugas National Park.

  • Spend an afternoon at Bahia Honda State Park.

  • Visit the Ernest Hemingway Home and Museum.