From Town & Country

Doing the same old thing isn’t usually something to look forward to. Novel experiences are filled with excitement and possibility. (Humans literally evolved to pay attention to new, flashy — and potentially dangerous — things, even more intently than familiar things.)

And nowhere does this seem to be more true than when it comes to travel. We’re urged to cover new ground, visit unseen locations, add more stamps in our passports — the ultimate family vacation. And when the average American gets just ten paid holidays a year, who wants to spend those precious days going over the same exact pathways year after year?

Me! I want to! Not all the time, and not on every vacation, but there’s something about returning to the same spot over and over again that works for me. Case in point: about seven years ago, my husband, my then-3-year-old daughter, and I visited the South Seas Island Resort in Captiva, Florida — a charming little spit of land just off the coast near Ft. Meyers. The weather was perfectly warm and breezy, there were dolphins frolicking just within my view every morning, and my daughter ate crispy french fries by the pool every single day (in between some rather epic tantrums).

A few years later, we returned, this time with a new addition toddling around, our second daughter. And in December we went again, for our third visit in just a handful of years. And while I do have an itch to explore different parts of the country — or even other parts of Florida — there are a bunch of reasons why we keep coming back.

Fewer rookie mistakes.

The first time you go anywhere or do anything, you can’t know all that you don’t know. You don’t know that the lobby actually has several large refrigerators so you can store the groceries you bought while you wait for your room to be ready. You don’t know about the shortcut that bypasses the traffic. You don’t know the nearby restaurants that are rip-offs from those that are sublime.

Yeah, yeah, I know that sometimes it’s on those unexpected detours or the hapless afternoons that the best memories are made, but I also think that when you’re in the market for a real break from the daily grind and you have small children, the fewer surprises the better. Now we know which area of the resort suits us best, what to ask for in terms of room location (if available), and stuff you can only find out after trying things on for size. (For the record: at South Seas we are marina view people, all the way, so we can glimpse both dolphins and manatees.)

You can measure time in sweet, surprising ways.

On our first visit to the resort, we couldn’t leave our daughter unattended for two seconds near the pool, much less anywhere. Last year, she could swim without help and could finally partake in the water slides that had been out of her league on the first visit. (She’d gone to the top but chickened out, and it was the source of much distress.) This year, both girls will be big enough, brave enough, and good enough swimmers to be able to zoom down those water slides for hours and hours. It’s those kinds of benchmarks that I find charming, and sometimes truly allow me to see how much has changed.

Repeat visitors get special treatment.

This reason is a bit shallow, but it’s also realistic: When you go back again and again to certain hotels or resorts, they love it and sometimes show you just how much by giving you upgrades, freebies, perks, or other small tokens of appreciation. Who am I to turn down free drink coupons?

There are plenty of photo ops.

If you’re into taking pictures for the annual holiday card or get a kick out of posing the kids on the same set of steps every year, the repeat vacation is your time to shine. In Captiva, there’s a trolley that connects both ends of the property, and it runs continuously all day long. I’ve got a series of pictures of each of my girls, framed in the window of the quaint little trolley, wind blowing their hair back.

Learning to find the new in the familiar.

But here’s the tricky thing about going back to the same spot: As much as it may have been breathtakingly beautiful the first time, it can also sometimes leave you feeling less than excited on repeat visits.

The technical term for this phenomenon is hedonic adaptation — when an identical stimulus provides less pleasure the more it’s consumed. But just like there’s a case to be made for embracing boredom — for learning how to actually do nothing — I also think that there’s a certain challenge to be met here. How can we find new things to do? What have we not yet done? How can we still find joy in the same thing? For kids like mine — who seem to always be seeking the next shiny thing — I think there’s a lesson to be learned here in finding a deeper enjoyment in something they've done before.