What It’s Like to Work Year-Round in a Vacation Destination

During my summers in college I lived and worked on Cape Cod, Massachusetts. Only an hour or two from Boston, the population of Cape Cod swells by more than 250 percent in the tourist-heavy months of July and August. This influx of vacationers requires a host of seasonal employees to support them and keep them entertained. In the summer months jobs abound for people who can work in hotels, restaurants, boat tour operations, amusement parks, summer camps, golf courses, etc. Even the National Park Service and local law enforcement departments have to increase staffing levels to support the throngs of people lining up to get a choice spot at the beach parking lot.

For me it was an easy fit for a summer job. I worked six to seven days a week at a sandwich shop and waited tables at a restaurant. The first summer I lived with a local family (childhood friends from New Hampshire who had moved there) and met a local boy whom I dated throughout college. Through him and his friends, I got a bird’s eye view into the year-round economy. After college I stayed one fall through November and experienced the stark contrast of the Cape with and with out tourists.

Here are some things I learned that may help if you’re considering relocating to a place you love to vacation.

Steady Year-Round Employment Is Scarce and Limited

The best way to ensure year-round employment is to have a career in a profession such as healthcare, education, law or banking. Summers on Cape Cod can feel like a relaxed big city because there are so many people from New York and Boston vacationing there. But big-city or tech jobs such as software engineering, management consulting, social media marketing, etc., are all but non-existent. If you want to work in those types of fields, you will end up commuting 60 miles or more to the Boston area. Consider whether spending hours a day commuting is worth access to beaches that you’ll be too tired to enjoy.

To find the jobs that are there, networking with locals is key. It is truly small-town living where who you know is more important than your amazing resume. Many of these jobs are taken by people who grew up on the Cape, went away to college and came back to start their families. The more you can get to know them, the better chance you’ll have of finding professional employment.

Be a Jack-of-All-Trades

Many Cape Codders have a summer career and a winter career. A summer fishing tour boat guide might do housing construction in the winter. An elementary school teacher might run a refreshment stand in the summer. Other jobs that have seasonal fluctuations are UPS drivers and holiday retail. Seasonal flexibility also means that you can expect to work longer hours in the summer and also make more money, which of course needs to be saved to get you through the winter months when you might work shorter hours, if any at all.

Networking is key for these jobs as well. Someone’s husband or wife or friend or relative will be favored for a job over an outsider. If you’re working at a seasonal job already, and want to stay on, get to know the locals, particularly business owners. They are the ones who will keep you employed and pass your name along when they hear of something. Making substantial personal connections and letting them know all the things you can do will keep you top of mind when it comes time to switch gears.

Entertainment Options Decrease in the Off-Season

Some of the most popular restaurants and watering holes are shuttered after Labor Day. If you love a place like the Wellfleet Beachcomber or the Brewster Woodshed, don’t expect to go there in December. Many buildings that house popular summer businesses aren’t even insulated. Summer activities such as building sandcastles on a crowded beach might be replaced with strolling on a deserted beach. You may also find that you have to drive farther to get more variety. A small-town area like Brewster and Orleans can keep you entertained in July and August, but come fall you’ll find yourself wanting to venture toward Hyannis or even Boston just to experience some variety.

Retirees are Everywhere

Many seasonal vacation destinations have a reputation for attracting retirees for year-round living. Cape Cod is one of them. If you work in health services, this could be reason enough to move there. But if you are seeking the vibrant youth culture you find at a place like The Woodshed, go to where those people live, not where they vacation.

You are Free to Enjoy The Land Without all the People

A beautiful place is beautiful in every season. You won’t be diving into waves at Nauset Beach in January, but you can still enjoy watching the waves crashing on the shores while wearing a parka. The ponds might be frozen and the beaches covered with snow, but you’ll find a new appreciation for those special spots when they’re not thronged with tourists. Most year-round residents love it for exactly those reasons and breathe a sigh of relief come September. That’s what makes it worth it.

Even with all my local connections I didn’t choose to stay on Cape Cod past that one November. I knew I needed to live in a big city to do what I loved. But many of my friends are still there and are thriving as a part of the community of locals.