5 warm weather escapes for Boomers who are tired of cold holiday seasons

If you grew up with white Christmases, you probably have a soft spot for them.

However, how many more seasons of shoveling snow, driving on ice, and putting on three layers just to get the mail do you actually want?

Our environment shapes how we think and feel, and a sunny December can trigger very different choices than a dark, freezing one.

If you are a Boomer who is ready for your holidays to feel lighter, warmer, and a little more fun, here are five places that hit that sweet spot: Good weather, great food, and enough comfort and convenience to actually feel like a break.

1) Palm Springs, California

If you like your sun with a side of style, Palm Springs is holiday heaven.

In December, daytime temperatures usually sit around 67°F or so, with plenty of sunshine and very little rain.

You are packing a light jacket for the evening, not a parka.

What I love about Palm Springs is how easy it is to relax here: The town is mostly flat, the streets are wide, and a lot of the resorts are designed so you barely have to think.

Pool, spa, restaurants, all in one place; for joints that sometimes complain about stairs and hills, that matters.

Food wise, you are spoiled.

Upscale steakhouses and seafood spots sit right next to modern farm to table restaurants and very solid plant based menus.

A lot of chefs in the desert are leaning into Mediterranean flavors right now, which means loads of grilled vegetables, olive oil, beans, and fresh herbs.

You can eat light at lunch and still go big on dessert.

If you like movement, you can start your morning with a walk around the neighborhood looking at midcentury homes, or book a round of golf at one of the many courses in the valley.

Instead of bracing yourself every time you open the front door, you step into dry, golden light.

That alone can reset how you feel about the end of the year.

2) Puerto Vallarta, Mexico

If you want warm ocean water, cobblestone streets, and real culture, Puerto Vallarta is hard to beat.

December here is one of the best months.

Average daytime highs sit in the low 80s°F, with warm evenings and the dry season in full swing.

The first time I walked the Malecón—the oceanfront promenade—I remember thinking, "This is what holiday lights are supposed to look like."

Palm trees, ocean breeze, kids eating ice cream, street performers, the whole thing buzzing but not stressful.

From a food perspective, this is paradise.

You can go from fish tacos and bowls of fresh guacamole at a simple beach stand to white tablecloth dinners with tasting menus that lean into local produce, chiles, and citrus.

Even if you eat everything like I do, you will notice how easy it is to eat mostly plants here without even trying: Beans, rice, grilled veggies, mango, papaya, pineapple.

If you are the curious type, the old town has galleries, historic churches, and plenty of small cafes where you can sit with a coffee and people watch.

If you like being on the water, there are boat trips to nearby coves, snorkeling, and sunset cruises.

You can make this a full family holiday too!

Bring the kids and grandkids, agree that the only gifts are experiences, and spend your budget on boat rides, tacos, and time together.

3) Madeira, Portugal

If you are ready for something slightly more adventurous but still gentle on the body, Madeira might be your island.

Madeira sits in the Atlantic and is often called the island of eternal spring.

So, it feels neither hot nor cold (just pleasant).

What makes Madeira special for a holiday season escape is the combination of scenery and pace.

You get dramatic cliffs, lush hillsides, and small towns that still move on island time; you can wander Funchal’s markets in the morning, nibbling local fruit and bread, then take a cable car up the hillside and stroll back down through botanical gardens.

Food here is underrated because there is plenty of fresh seafood, but you also see a lot of rustic, vegetable heavy dishes and incredible bread.

Bolo do caco—a round, slightly chewy flatbread—is basically an excuse to eat garlic and herbs in public.

Pair that with grilled vegetables, salads, local wine, and fruit for dessert and you have a very heart friendly way to enjoy the holidays.

If you like walking, Madeira’s famous levada trails follow old irrigation channels through forests and along mountainsides.

You can choose easy, flat sections that still come with big views.

Think "long walk with a purpose" more than "intense hike".

Since Madeira sits in a European time zone, it also works if you are semi retired but still doing some consulting or remote work.

You can log on in the morning, close the laptop after lunch, then go chase sunsets.

For a lot of Boomers, this kind of trip doubles as a mindset shift.

You prove to yourself that you can still explore new places, try new foods, and navigate a different culture.

That sense of competence is better than any gift under a tree.

4) Scottsdale, Arizona

Some people love the ocean, while others want sunshine, big skies, and the smell of desert air.

If you are in the second group, Scottsdale is your spot.

In December, Scottsdale usually sees daytime highs in the low 60s°F, with dry air and only a handful of rainy days.

Local tourism boards actually argue winter is the best time to visit, with plenty of sunny, snow free days that are ideal for getting outside.

Scottsdale is packed with golf courses, spas, and hiking trails.

You can spend your mornings walking a gentle desert path surrounded by saguaros, then soak in a hot tub in the afternoon, then grab dinner in Old Town.

The food scene has leveled up a lot in recent years.

You will find Southwestern flavors, modern Mexican, and plenty of health conscious spots that lean into bowls, salads, and grilled everything.

It is a good place to experiment with that "eat colorfully" advice you see in nutrition books; think roasted sweet potatoes, black beans, salsa, charred corn, bright greens.

If you enjoy art, Scottsdale’s galleries and public art installations add some culture to the mix; if your body prefers a slower pace, you can simply base yourself at a resort, book a massage, read by the pool, and let the desert do the emotional reset for you.

This is a great destination if you live in a cold US city and want minimal time zones and no passport drama, but still crave a holiday environment that feels completely different from home.

5) Florida Keys, United States

Finally, if you want tropical water without pulling out your passport, the Florida Keys are a pretty dreamy option.

In December, the Keys typically enjoy daytime highs around the mid 70s°F, with comfortable evenings and relatively low humidity.

Travel writers often call winter the best time to visit because you get plenty of sun and warm water, without the worst of the summer heat or rain.

Key West in particular is an easy home base; it is walkable, colorful, and has that slightly eccentric, laid back energy that makes it perfect for people who are done pretending the holidays have to be serious.

Here the food leans Caribbean and coastal: You will find fresh salads, tropical fruit, black beans and rice, grilled fish, and yes, lots of Key lime pie.

It is also simple to eat light at breakfast and lunch, then enjoy a bigger dinner without feeling like you are overdoing it.

The real magic is how much time you can spend outside: Morning coffee on a porch instead of at a frosty window, and afternoon snorkeling, kayaking through mangroves, or just sitting by the water.

Sunset is basically a daily event here, especially in Key West where people gather in Mallory Square to watch the sky do its thing.

Closing thoughts

Cold holiday seasons are familiar, but they are not mandatory.

You can choose to trade snow for desert hikes, cobblestone streets, island forests, or tropical water.

Each of these places gives you something slightly different—some are more active, some slower, some more urban, some more wild—but they all give you warmth and light at a time of year that is usually the opposite.

From a self development angle, this is bigger than a vacation.

It is a way of saying, "I am allowed to design the next chapter of my life on purpose."

You are not stuck with the script you grew up with.

Here is a simple question to sit with: If you gave yourself permission to skip winter just once, which of these spots would you pick?