From fantasy to reality: 7 lessons from moving to a vacation hot spot
“We live two miles from the beach, and we can never seem to get over there.”
While away on vacation, I spend half the trip fantasizing about what it would be like to move to whatever distant locale I’ve run off to. The Bahamian-style porches of Key West, the brightly colored row houses of Copenhagen — no Zillow listing is safe as I dreamily scroll through real estate for sale.
The people we become on vacation are, in a sense, our best selves. We are freer, distanced from the daily grind of work and household upkeep, focused only on pleasure and the excitement of new experiences. Who wouldn’t want a slice of that all year long?
In 2019, my husband and I purchased our first home, in the beachside vacation town of York, Maine, where the population just about doubles in the summer. Over these past five years, I’ve gotten a taste for what it’s actually like to live in a vacation town, and have spoken to others about their experiences. Here are seven things I’ve learned:
1. It’s going to require patience and creativity
My husband and I started to notice that there’s a window each spring when takeout orders get wonky. It coincides with the time of year when restaurants are training new staff to handle the influx of customers. (Just ask them to repeat the order, and you’ll be OK.)
One of my favorite things to do is visit the beach early in the morning before work, or in the evening when everyone has retreated for the day. Eating at restaurants during off-peak hours or saving your favorite spots for the shoulder season when summer ends are other ways to escape the masses.
2. There’s the potential for frequent houseguests
I have a friend who lives on the Cape and keeps a guest room perpetually at the ready. “It’s your room,” she likes to tell me, but I suspect maybe she says that to everyone.
Living in a popular vacation spot means that friends and family are more motivated to visit, especially during the summer. For some, this is part of the charm. But if you’re not into company, then the solution is pretty simple: Don’t set up a guest room.
3. You are no longer on vacation
As the owners of the Captain Farris House, a bed and breakfast in Yarmouth, Jeff and Carol Watson say March to December is spent devoted to the needs of their guests.
“We live two miles from the beach, and we can never seem to get over there,” Jeff said.
Carol called it a “catch-22.”
“By the time we have a chance to breathe for a period of time where we can take advantage of it, it’s cold,” she said. “But I wouldn’t have it any other way.”
4. You’ll see the good alongside the bad
Molly Coogan and her husband took ownership of Bunch of Grapes Bookstore on Martha’s Vineyard in 2022, an island mainstay that remains open year-round. Coogan grew up visiting the Vineyard and spent summers there in college, then eventually landed there full time in 2011 with husband Brendan and their two children.
“You see the cycle of the year,” Coogan said. “You’re not dealing with crowds in the offseason, and you’re working. In the summer it used to be pretty carefree for me, and now that’s when I have to work the hardest.”
Though going away on vacation can be an escape from the challenges of home life, the reality is that locals are dealing with their own stuff the same as anyone else.
“I do love living here, and I think it’s such a special place, but I’m also very mindful of the many people for whom it’s not,” Coogan said of the Vineyard. “It’s not this playground of the rich and famous that it’s perceived to be. Particularly in the offseason, there is poverty and addiction issues and mental health issues and limited resources to deal with those things.”
5. The housing market can be competitive
A place like Martha’s Vineyard only has so many homes to go around, which has created a housing shortage for islanders, forcing many to flee in the past decade. The average house price there is $2.3 million, which is twice what it was 10 years ago. Short-term rentals aren’t any better, averaging about $931 a night.
Up north in “Vacationland,” there are similar challenges, as residents struggle to find affordable housing. According to the Maine Association of Realtors, the median price for a house sold in the state topped $400,000 in September — putting many homes out of reach in a place where the average household income can hover around $73,000.
6. You could be eligible for a tax break
As both an incentive and reward for year-round residents, Maine has something called the Homestead Exemption Program, which is essentially a tax break for anyone who lives in the state all year. You can download the form online; Once accepted, residents can have a home value reduction of up to $25,000 for property tax purposes.
7. You’re constantly reminded why you love it
For Sara Fitzgerald O’Brien and Miles O’Brien, the couple behind the York, Maine-based lifestyle brand Sara Fitz, appreciating the natural beauty and tight-knit community of their small beachside town will never get old.
“It feels like a combination of ‘Gilmore Girls’ and ‘Dawson’s Creek,’” Fitzgerald O’Brien said of York.
They go for long drives around town almost every day, savoring the coastal views and forever reminding their two children how lucky they are to live here. It’s a place where the school bus drives past the beach and where kids still walk to the library. It’s a location that inspires much of Fitzgerald O’Brien’s signature watercolor artwork, and a place the couple said they never want to leave.
“Miles and I, on a daily basis, multiple times a day are like, ‘We love being here,’” Fitzgerald O’Brien said.
“It is an incredible luxury, and we never take it for granted.”
Nicole Cammorata can be reached at [email protected]. Follow her on Instagram @nicolecammorata.
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