5 Great Snowbird Destinations

Looking to trade snow boots for sandals this holiday season?

Whether you're chasing sunshine, palm trees, or just a break from the cold, these warm-weather destinations are perfect for your winter escape.

Palm Springs, California

If you're looking for a winter escape with a little more flair, Palm Springs delivers. While Arizona offers reliable warmth and desert beauty, Palm Springs adds a touch of retro glamour to the mix. Once the playground of the Rat Pack, this desert oasis blends mid-century style, mountain views, and a vibrant arts scene. It may not hit the 90s every day, but what it lacks in heat, it makes up for in panache. While the spirit of Dean Martin may still occasionally staggers through town, Palm Springs is far from a ghost town. It’s a straight-line drive from L.A., so it gets plenty of winter action.

It’s a surprisingly open and welcoming town, capped off by a 26-foot-tall statue of Marilyn Monroe as she appeared in the iconic shot from the movie The Seven-Year Itch.

One of the other nice things about Palm Springs is that if you do get a hankering for some good old 30-degree (Fahrenheit) temps, the mountains are not far away.

As far as western winter destinations go, Palm Springs is the cool place to stay warm. Nothing wrong with that.

Gulf Shores, Alabama.

Looking for a warm, welcoming place to spend the winter without the crowds and chaos of bigger destinations? Gulf Shores might be just what you're after.

Tucked into Alabama’s small but stunning stretch of Gulf Coast, this town offers everything a snowbird could want: friendly locals, warm waters, fresh-off-the-boat seafood, and golf courses that rival any in the region. If your ideal winter includes flip-flops, an orange polo, cruising around in a golf cart, and maybe growing a snow-white Van Dyke, Gulf Shores is the perfect place to make it happen. Guaranteed.

Hilo, Hawaii

If you can swing the rent, one of the best places in Hawaii to over-winter is around Hilo. Another destination historically popular with Canadians, the Hilo area offers a good stock of rentals, a small-town vibe, and … well, Hawaii. This is what a true tropical paradise looks like, and if that sounds like a good place to spend the winter (and it should), this is the place you need to be.

Also Read: The Ultimate Beach Trip Packing Checklist

Puerto Vallarta, Mexico

Cancun moves slightly down the list (though there are lots of options for winter rentals in the area from Cancun to Tulum) and Puerto Vallarta moves up.

Why Puerto Vallarta? It has a strong tourism infrastructure to support snowbirds, many well-established housing communities for them to stay, plus all the great things that go with living on the Pacific Ocean in Mexico – beautiful beaches, great seafood, and a truly relaxed lifestyle.

Mexico is a great choice for folks looking to winter in a different country. It’s a standout in an already great lineup.

Medellin, Colombia

Medellin gets rave reviews for its architecture old and new, its arts scene and of course its coffee.

Medellin is popular with snowbirds from Europe, so if you’re looking for a different perspective on snowbirding and life in general, you’ll set it in Medellin.

Madeira, Portugal

Another winter destination popular with Canadians, Madeira is Portugal at its warmest.

Madeira is an island between Morocco and the Portuguese mainland in the North Atlantic, and while that restricts your getting-around-ability, it also gives you all the fun things about living on an island – easy access to beaches, fresh seafood, and such – with a more cosmopolitan feel than you might get in the Caribbean.

Because Madeira is actually closer to Morocco than Portugal you get two cultures for the price of one, making it an intriguing choice for a winter’s stay.

Also Read: Americans in Portugal: Your Destination Guide

Auckland, New Zealand

In case it hasn’t popped up in your news feed, it’s summer in New Zealand when it’s winter in the U.S. That coupled with the fact that you’ve always wanted to visit New Zealand makes it kind of a no-brainer to actually live in New Zealand for the winter.

Well, there are mitigating circumstances. Airfare is pretty steep. And New Zealand can be breathtakingly expensive. And the local time is all completely different from wherever you are in the United States. But the cricket is world-class, and that may be worth paying for.

Those issues aside, for one winter … to do something you’ve always wanted … in a place you’ve always wanted to visit … why not?

If that’s your final answer, remember that Generali Global Assistance has vacation-rental insurance custom-made for snowbird stays in addition travel insurance with assistance services.

Getting a quote is simple and getting covered is a snap. Try it yourself.