Same Time, Next Year: Repeat Vacations Are Kinda Chic

There’s something kind chic about going back to the places you love.

You all know I love planning trips to new places, sure, but I keep ending up in the same handful of spots, year after year… Hilton Head, Vail, SoCal. But before you judge, this mundane idea of travel may be a modern trend. Research shows 1 in 3 Americans return to the same vacation destination annually. Kind of boring? For some yes. But for 30% of us, it’s kind chic. So why keep going back when there’s a whole world left unexplored? For me, it comes down to a few things… and they’re more sentimental than strategic.

Nostalgia and tradition

Growing up, our family of seven took an annual trip to northern Michigan… a self-catering cottage at a resort near a lake. We did this for about ten years straight, and since it was our only real vacation of the year, we counted down to it all summer. I still have vivid memories of those weeks: running around the resort, meeting other kids, getting into harmless trouble, all of us carefree, checking in with the adults only when we were hungry. A week felt like it would last forever. It was the old-school, quintessential American summer trip, and it’s a core memory for me.

Decades later, I find myself wanting to build that same nostalgia for my own family. HHI, Vail, and SoCal have become our modern-day northern Michigan…places that fill our days with laughter and our hearts with the kind of memories that, someday, I hope get passed down to my kids’ own families.

Ease of planning

When you keep returning to the same places, there are fewer unknowns to plan around. When we go to HHI, we already know what we like and don’t when it comes to restaurants, shopping, beaches, and rentals. That makes the whole trip easier to plan – less time spent researching and second-guessing, more time actually relaxing.

Feeling like a local

Go back to a place enough times and you start to feel less like a tourist and more like visiting family. Over the years you learn where the locals actually eat, shop, and spend their time – the tucked-away spots most tourists never find. We don’t live in any of these places full-time, but there’s something fun about seeing familiar faces at our favorite resorts and cafés that makes my heart smile.

You return for a reason

Every one of our repeat destinations has one thing in common: they deliver, trip after trip. We keep going back because we know exactly what we’re going to get- a great vacation, period.

So no, I’m not heading to a new destination in Europe every summer. Some years, going back to our family favorites beats going new….and northern Michigan taught me that a long time before HHI, Vail, or SoCal ever did.