“How we found our forever Vrbo”

For many travelers, anticipation can be the happiest part of any vacation. But I’d contend that anticipation preceding a trip you’ve made many, many times before may be the sweetest kind of all.

At least it feels that way whenever my family drives to our regular vacation rental on Kiawah Island, off the coast of South Carolina. A low-slung cottage three minutes from the beach, it’s cozy rather than palatial, and that suits us fine. I know, like a homing instinct, that it’s in reach as we leave the highway and cross the bridge from the mainland—everyone’s signal to roll down the car windows, breathe in and savor a first gulp of salty Atlantic air. After this bridge comes 15-ish miles of Spanish moss and sweetgrass marshes before we’ll cross the Kiawah River and finally arrive on the island. And that after we roll through the resort gates, we’ll run down to the beach and dip our toes into the ocean for the first time.

Or rather, the thousandth time. I’ve been going to Kiawah for at least 30 years—first as a kid, now as a parent. When I had my twins in 2014, the first vacation my husband and I braved was to Kiawah, with my parents. Back then, the babies were 10 months old and shoveled handfuls of sand into their mouths every time they crawled off the beach blanket. We returned in summer 2019 as a family of five (more kids, less sand consumption), and made it back again last summer.

Traveling, but stress-free

Some people visit Kiawah for the golf. For us, trips to the island aren’t about doing very much of anything, except, of course, spending time together. Here there are no museums (unless you count the Heron Park Nature Center), no hot restaurants, no strictly scheduled tours. What we come for is the opportunity to be together, reconnect and make new memories—easy in a place this beautiful, on a beach this wild and windswept. You can’t help but slow down to watch a lizard climbing a boardwalk post, or to stop in the middle of a traffic-free street to listen to cicadas crescendo in the surrounding trees.

It helps that we got lucky with the Vrbo rental my parents found for that first multigenerational family vacation in 2014. A weathered gray clapboard cottage with three bedrooms, it had a renovated kitchen (equipped with an ice machine and blender—the better to make frozen cocktails in), a deck with a charcoal grill (perfect for low-stress dinners at home) and a living room with a coffee table that proved just the right size for heated rounds of Scrabble. It suited us so well, in fact, that we rented the same house on our two subsequent trips. Whenever we get to go back, I’m sure we’ll want to stay there again.

Part of the joy of returning to the same house is that all the little unknowns that can add stress to the settling-in phase of a vacation (will there be enough beach towels? Does the kitchen come with olive oil, or do we need to buy it? Do the bedrooms have blackout blinds?) become knowns. Return visits feel both optimized and frictionless. Stay in the same place time after time, and that sweet sense of vacation anticipation becomes highly specific. You’ll note small changes with appreciation (a soundbar below the TV and new sheets on all the beds—how lovely!), because whatever was there before was already more than fine.

The prospect of going back also infuses the initial visit with the air of a research mission. So often on vacation, you only learn about special experiences once it’s too late to enjoy them. Now we know where to spot dolphins and alligators, how to book sunrise beach yoga sessions, and where to park our bikes on visits to the Beaches and Cream ice-cream parlor (an optimal riding distance for little legs to pedal, as long as there’s the promise of a cone at the end).

Familiarity breeds content

Some might consider this repetition boring or unimaginative. To which I’d respond that the rest of my life as a working mother of three in a big city is unpredictable enough, thank you very much, and sometimes it’s soothing to know what we’re in for. It’s a genuine, full-stop kind of break—a relief for anyone who’s usually the Keeper of the Family Mental Load. That familiarity is a balm for kids as well as adults who appreciate strong routines. By our third family trip to Kiawah, the kids knew which beds they wanted in the cottage, and I knew exactly where I’d find Callie’s Hot Little Biscuits in the frozen aisle of the supermarket—wins all around.

There are countless reasons that people across the world return to the same spots year after year (French families go back to not only the same town, but the same spot on the beach). We keep going back because Kiawah works for us, and for considerations that are less practical, more emotional. Last summer, I couldn’t resist swiping back on my phone to show the twins, by then eight years old, photos of themselves crawling on the beach as babies. And a picture of my late dad, their beloved Papa, holding my dimpled-thigh babies in the surf, his head thrown back in laughter—an image that still radiates love.

It’s gratifying to layer memory upon family memory. Go back to a beloved place enough times, and those memories linger, the same way cicada symphonies seem to hang in the silence right after they stop.