When’s the Best Time to Travel? Here’s What Works for Our Family

When’s the Best Time to Travel? Here’s What Works for Our Family

Do you have a favorite time of year to take a family vacation? For some families, it’s all about summer road trips and beach days. Others crave fall getaways with cool air and apple cider. And let’s not forget the winter travelers chasing sunshine while the rest of us shovel snow.

Truth is—there’s no one-size-fits-all answer when it comes to travel timing. The “perfect time” really depends on your family’s needs, school schedules, budgets, and how you want to feel on vacation. Do you want excitement and buzz? Quiet and calm? Somewhere in between?

Over the years, we’ve tested nearly every season—and while there are pros and cons to each, one month has quietly become our go-to: February.

Here’s what we’ve learned along the way (and why you might want to rethink your usual vacation calendar, too).

🌞 Why Summer Is a Classic (But Busy) Travel Season

For most families, summer is the default time to travel—and for good reason:

  • Kids are out of school

  • The weather is generally great across most destinations

  • It’s the season for outdoor fun, pool days, and national park adventures

From a flexibility standpoint, it just makes sense. You don’t have to pull anyone out of class. You can plan longer trips without worrying about homework or attendance. And the sunshine alone can feel like therapy after a long school year.

But here’s the catch: everyone else is thinking the same thing.

Airports are packed, hotel prices surge, and you’ll need to book months in advance just to score a decent room near the beach. Restaurants, theme parks, and popular trails can get so crowded they’re more stressful than fun.

☀️ PackyGo Tip: If you’re set on a summer trip, try looking for hidden gems—places just outside major destinations. You might trade Disney crowds for a charming lake town or opt for a beach that's more shells than selfies.

❄️ Why February Is Our Underrated Family Travel Secret

Now here’s the part that surprises people: our favorite time to travel as a family is February. Yes, the middle of winter. Yes, with school in session. And yes—it works.

Here’s why:

  • Tropical places are warm but not sweltering

  • It’s typically drier than the summer rainy season in beach destinations

  • Crowds are smaller (especially after the holiday rush)

  • Flights and hotels are cheaper than spring break or summer

We’re not saying it’s always easy. We do have to coordinate with teachers, pack some homework, and sometimes bring devices for remote check-ins. But when we’re sitting on a quiet beach, sipping smoothies while everyone back home is digging out their driveways? Totally worth it.

It’s not just about sunshine either. February gives our family a much-needed mental reset. After the holiday chaos and the cold January blues, having something to look forward to gets us through those long, gray days.

🧡 Family bonus: We always come back feeling closer, lighter, and more energized. And isn’t that what vacation is really about?

🏞️ What About Summer? We Just Head for Higher Ground

That said, we don’t skip summer travel—we just change the destination.

Instead of sweating it out in crowded amusement parks or overpriced resorts, we head:

  • North to lake towns

  • Into the mountains for hiking and fresh air

  • To national parks with cooler temps

There’s something special about sipping coffee on a cabin porch while the kids skip rocks at the lake. Or hiking in the morning and spending the afternoon reading in hammocks. These types of trips feel slower, more peaceful, and just as memorable.

📆 Planning is still key, though. The secret’s out on these destinations, and spots fill up fast—sometimes by spring. So once you know your travel window, start locking things in early.

💡 How We Choose Our Travel Timing

There’s no formula that works for every family, but here’s what we look at when deciding when to travel:

  • School calendars (but we stay flexible when it matters)

  • Weather at the destination (hello, hurricane season avoidance)

  • Crowds and local events (festivals can be fun or overwhelming)

  • Budget—flights and lodging can vary wildly based on season

  • Energy levels—sometimes we need rest, not adventure

Over time, we’ve learned to stop chasing “perfect.” Instead, we ask:
What do we want from this trip? Do we need sun? Quiet? Connection? Once we answer that, the timing becomes a little clearer.

🧳 Final Thoughts from Our PackyGo Family to Yours

There’s no universal best time to travel—but there is a best time for your family. For us, February checks a lot of boxes: fewer crowds, better deals, and a mental boost during winter. And in summer? We skip the crowds and head for nature, where we can breathe a little easier.

No matter when you go, remember that how you travel matters just as much as when. Keep it simple. Stay flexible. Focus on what will help your family reconnect—and don’t be afraid to take the road less traveled (even if it’s in February).

Because the best memories aren’t always made during peak season…
Sometimes, they’re made when you break the rules, pull the kids out of school for a few days, and say: “Let’s go somewhere warm.”

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