What’s the best time of year to take a vacation?

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By Christopher Elliott

What’s the best time of year to take a vacation? For a select few places, it’s any time.

I just drove through Breckenridge, Colo., on my way back home to Arizona. I’d visited this Colorado mountain resort in the fall (in the 90s and 00s), in the winter (every decade since the 80s), and in the spring (almost every year). But never in the summer — until now.

I think Breckenridge is my one-word answer to anyone who asks me about the best time of year to take a vacation. If you choose the right place, you can go at any time. But beware of any destination that bills itself as a “year-round” resort. There are always qualifiers. I’ll explain in a minute.

The best time of year to take a vacation. Christopher Elliott, author
Iden Elliott rappels down the last tower at the ziplining course in Breckenridge, Colo.

A resort for all seasons? It’s possible

The first time I visited Breckenridge, in the fall of 1997, I was curious about what travel experts euphemistically call “shoulder” season — the time of year when few people want to be there because school is in session. And I was skeptical. Could any resort call itself “year-round” without bending a few facts?

I found plenty of reasons to be there.

The hiking in Breckenridge is incredible, with an abundance of fourteeners — peaks over 14,000 feet. But during the fall, with the leaves on the aspens yellowing, there’s an extra layer of color to appreciate from the trail.

I returned in 2015 with my kids, and we made some less challenging hikes downtown and along the Sawmill Creek Trail. Still as picturesque as ever, with those snow-capped mountains inviting us to return later in the year.

Winter and early spring are prime time for skiing. In fact, we couldn’t find accommodations in Breck a time or two and had to find lodging in nearby Frisco (no hardship, since it’s close to all the great grocery stores) or just stayed in Denver (also nothing to complain about). Frisco, of course, has the Frisco Adventure Park, one of the best snow tubing hills for kids.

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I won’t belabor the point about skiing, except to say that I live for a powder day and an early morning run down Zoot Chute off Peak 8. The last time I took the plunge, my kids weren’t old enough to ski with me. Now they know better than to follow Dad into the abyss.

But still. Skiing in Breckenridge is awesome. Enough said.

Iden Elliott tours the Vail Farmers Market in Vail, Colo.
Iden Elliott tours the Vail Farmers Market in Vail, Colo.

Is summer the best time of year to take a vacation?

When it comes to the best time of year to take a vacation in Colorado, you hear a lot of about summer. But come on. There’s no snow, except on the top of the mountains. It’s not enough to ski on.

And that’s the dilemma of many year-round resorts. How do you persuade them to come at a time of year they’re not exactly known for? For example:

Los Angeles in the fall. Santa Ana winds, wildfires. I rest my case.
Miami in hurricane season. Does anyone want to be there when a Cat 5 is bearing down?
Chicago in winter. Can you say “frozen”?

Breckenridge doesn’t really have those problems. When I visited the resort in late June with my kids, we found plenty of things to do and plenty of visitors trying to do them. People crowded onto the new zipline course. The mountain biking trails were packed too. Plus, it was a perfect time to be in the mountains, with Denver and Fort Collins suffering through a triple-digit heat wave. On the mountain, you needed a fleece to stay warm. My kind of summer.

The entrance to Breckenridge's off-season activity area for mountain biking and zip lining. In winter, this is also a terrific run.
The entrance to Breckenridge’s off-season activity area for mountain biking and zip lining. In winter, this is also a terrific run.

How to tell if your resort is year-round

I’ll hand it to Breckenridge: It’s a four-season resort. The question is, how do you find a Breckenridge close to where you live?

Talk to your kids and review your past vacation itineraries. If there’s a place you find yourself going back to again and again, chances are you’ll like it during the off-season, shoulder season, or any season. It’s a little subjective. My kids are dying to go back to Temecula, Calif., where the weather is always the same. But they don’t care. They love that little downtown area, the restaurants, the hiking, and the hot-air ballooning.

Check the marketing. Some vacation destinations know better than to pitch themselves as a place to visit when the weather is too hot or too cold, or during hurricane season. While you might find some terrific deals during those off-peak times, you’ll need to understand that it’s not going to be the same. Ocean City, Md., during winter, is not Ocean City, Md., in the summer, for example. Not even close. But if you love Ocean City, you might like it cold.

The best time of year to take a vacation anywhere, of course, is when you need a vacation. Not when your travel agent, or some destination’s social media account, summons you. Go when you’re good and ready — and have a good time.

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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. He is based in Panamá City.

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