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The case for taking the same vacation every year

WASHINGTON (THE WASHINGTON POST) – I get this sinking feeling at the end of a trip to a new place. It’s not the regular end-of-vacation blues or the Sunday ‘scaries’ of having to go back to real life.

I become overwhelmed with nostalgia for somewhere I haven’t even had the chance to miss. I begin to think wistful thoughts: I may never be in this place again. This may be my only chance to walk this street or see this sunset. Everything will just be a memory.

But there’s a balm for the melancholy: When a place feels special, I plan a trip back – over and over again.

From TV shows to social media, we’ve been trained to think travel should be a bucket list we check off. One-and-done. Been there, done that. There are so many places to see and so little time and funds! Why waste time on going to the same place twice?!

I grew up spending most of my summers at the Jersey Shore. All year I looked forward to the week our family would get a house in small town called Lavallette. We loved talking about what we’d do this year – even though we knew exactly what it would be. We’d get ice cream at Salty’s and fried fish at Berkley’s and, of course, pizza at Lenny’s. Remember that game we played last year? We should do that again.

Returning to the same destinations allows you to create a routine when so much in our daily lives can feel chaotic and uncertain. There’s a comfort in a familiar place. Plus, you can even pretend like you’re a local. You might find a favourite coffee spot or maybe even get to know the neighbours of your rental if you’re a repeat renter.

It also lets you to see how a city evolves. It’s the reason I’ve gone back to Las Vegas more than five times since I moved away from the city more than a decade ago, even as most of my friends have moved. I love its story arc from a recession-battered town when I lived there to a destination for sports and art.

This handout photo shows the author and her family in Livingston, Montana in 2022. PHOTO: THE WASHINGTON POST

Sure, once-in-a-lifetime trips have their purpose, and I’m not knocking them. They open our eyes to new cultures and places. When we do them right, they can be life-changing or even the kick-off of your repeated trips.

I know I’m not alone in this feeling. One friend has been going on the same vacation in the Northwoods of Wisconsin with her family for more than 20 years. They even have something called the “Rhinelander box,” which has all the supplies they need for the trip. She knows exactly what to pack and what to expect – there are no surprises. Another friend’s family took the same beach vacation, at the same hotel, in the same room for more than 30 years. The hotel would make an announcement on the loud speaker when the family would arrive, she said. Those are memories for a lifetime.

My partner grew up going to the Paradise Valley in Montana every summer – fly-fishing, hiking and horseback riding with his family. When it came time for my family to take our first trip to the Yellowstone area, we had a built-in tour guide. Seeing the wonder of the place through his eyes gave me a deeper appreciation for the beauty of Big Sky country and a peek into his younger self.

We started some of these traditions of our own during the pandemic. We’re on our fourth year of renting the same house in the Outer Banks, rotating different crews of friends and family with us each year. We’ll take my family to Italy this year, a place we’ve both been, so my mom can see where her grandparents are from.

The Inn at Perry Cabin in St Michaels, Maryland, has become “our” place; it’s a peaceful slice of luxury close to home. We kept saying “we have to come back here” on our first visit – and then we did. We pretend that the yearly splurge is for the dog, who also seems to love it, but who are we kidding? – Amanda Finnegan

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