Want a warm-weather vacation with your family? Read this first

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By Christopher Elliott

If you’re reading this, you’re probably cold. You’re thinking of a warm-weather vacation with your family. You deserve one.

And you can have one — but it’ll cost you.

I’m not even talking about the money, although if you’re trying to get somewhere remote, it could set you back a few grand. I’m talking about the tradeoff, the very real cost of exchanging snow and ice for tropical heat. As someone who just spent a month in California and Hawaii with three kids, I can tell you that warm weather has advantages and disadvantages. Knowing both can help you make a more informed decision about escaping bad weather.

The vacation rental company FlipKey recently surveyed customers on their top warm-weather destinations. Florida, South Carolina and Arizona top the list of places people want to go. Chances are you have your own place in mind — maybe a little place down in the Florida Keys or a secluded beach on Kauai.

The perils of warm-weather vacations

I feel duty-bound to talk about the dangers of warm-weather destinations. Tourism brochures and websites like to present these places as paradise on earth. They are not. I know because I used to live in one of those warm-weather paradise-like vacation destinations, a little town in Central Florida called Orlando. The Magic City had it all — nice weather, exciting theme parks, and a terrific airport. It also had oppressively hot summers that featured monsoon-like rains every afternoon, aggressive cockroaches the size of your thumb, and more than its fair share of crime.

We had similar issues on Hawaii’s Big Island on a recent visit. So pretty to look at, but living there for a month was another matter. We rented a small place on the Hilo side of the island, which I like to call the forgotten part. Forgotten, because little over 10 percent of the island’s visitors make it out there — the rest stay on the more touristy Kona side. Also, it rains. A lot. (Related: It’s cold out there — don’t you wish you were here?)

Since our vacation rental didn’t have an air conditioner, we had the windows open 24 hours. At night, the sounds of the screaming tree frogs — TWEEET! TWEEEEET! TWEEET! — were drowned out by the torrential rains. A time or two, I thought our house was going to slide off the cliff into the Pacific.

And did I mention the volcanic eruption? That’s a whole ‘nother story. Fortunately, Kilauea was quiet while we were there, but still. Paradise has its costs.

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And yet, for all the potential downsides, Hawaii is beautiful. Unrealistically beautiful. Every picture looks like a postcard. Every day is summer. It’s like a dream.

Who wouldn’t want to be there in the middle of the winter? That’s a trick question. If you turn on the radio in Hilo, you hear them giving away trips to Las Vegas, and when you talk to people in Hawaii they ask about the mainland. Perhaps it’s human nature always to want what you don’t have.

Thinking of a warm weather vacation?
Iden Elliott in Savannah, Ga., one of his favorite warm-weather destinations

No such thing as a perfect warm-weather vacation with your family

Truth is, you’ll never find a perfect warm-weather vacation destination for your family. Even when you think you have, you’ll discover the blemishes — the not-so-perfect things that make you want to visit another place.

One of my middle son’s favorite destinations, Savannah, is the only warm-weather destination that seems to have embraced its imperfections and even elevated them to an art form. Savannah has hot summers and mild — sometimes cool — winters. Its downtown is both quirky and historic but far from squeaky-clean. They seem to like it that way. Also, this is where my family hit the shores of America a century ago, so it holds a deep meaning for the Elliotts. (Related: What is FlixBus and why did it leave them stranded?)

I see Savannah as a metaphor for warm-weather vacations. You will find warmth, but you will also find something else — more people, high prices, maybe crime. And it will be fine. Then you’ll return and say, “There’s no place like home.”

Erysse Elliott in Sedona, Ariz
Erysse Elliott in Sedona, Ariz

For the almost-perfect warm-weather vacation, plan ahead

You can still have an almost-perfect warm-weather family vacation, or something close to it. As someone who is based in a warm place (Arizona) and is currently writing a story from a warm place (Hawaii) I can tell you — it’s possible. (Related: Think vacation rental management companies aren’t worth it? You’re wrong.)

Don’t go too far. A lot of families immediately think of Florida, California or Hawaii. You don’t have to drive or fly far to find warmth. South Carolina and Georgia are pretty nice at this time of year, too. If you live in Northern California and need to get out of the cold, try Los Angeles or Santa Barbara. (Here’s what you need to know before you rent your next vacation home.)

Set realistic expectations. Winter happens even in warm destinations. LA gets cloudy and even cool. It can snow in Georgia and South Carolina. Don’t promise your family fun in the sun. The weather gods may not deliver.

Ignore the tourism propaganda. Wherever you go, you’ll find crowds of visitors who want the same thing. So wipe that image of the deserted beaches out of your mind. You’re probably better off ignoring the tourism websites and reading the local online newspaper to get a more realistic idea of what awaits you.

I’m taking the road less traveled. When everyone else hits the west coast of Florida, I like to head north to a little area called the Forgotten Coast, which is a little cooler, but abandoned in January. It’s also a good time to see one of my favorite Arizona destinations, Sedona.

Escaping to the warmth has its advantages and disadvantages. But if you take a little time to research your destination, you can have an experience that’s as close to perfect as it gets.

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Christopher Elliott

Christopher Elliott is the founder of Elliott Advocacy, a 501(c)(3) nonprofit organization that empowers consumers to solve their problems and helps those who can't. He's the author of numerous books on consumer advocacy and writes three nationally syndicated columns. He also publishes the Elliott Report, a news site for consumers, and Elliott Confidential, a critically acclaimed newsletter about customer service. If you have a consumer problem you can't solve, contact him directly through his advocacy website. You can also follow him on X, Facebook, and LinkedIn, or sign up for his daily newsletter.

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