“At your swimming location of choice, alternate between napping, reading, and swimming. I just do those three things and chill”
Photo-Illustration: The Strategist Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations/itineraries possible.
1 p.m. Pick up discounted Chianti I always stop at the NH Liquor & Wine Outlet in Portsmouth, New Hampshire, which is literally on the highway. It’s a tax-free liquor haven with great prices. They don’t have natural wine, but you can find some Chianti, which is a joke I have with my friend. We get whatever else we’re feeling on the day, and bring a mix of things because I want to be a good guest.
Day 2 8 a.m.: Make an early run for coffee I’m a freak in Maine and wake up with the sun. After sitting in the car for a million hours the day before, I like to start my morning with something active. At 8 a.m., I will run to Green Tree Coffee & Tea . It’s a 15-minute run or two-minute drive from the Lincolnville Motel. They have amazing coffees and teas. They are fanatical about what and how they brew. I get a cold brew or a double espresso depending on the temperature that morning.
10 a.m.: Stock up on bug spray and Carhartt Stop by any Renys on your way to swim. Renys is a Maine department store that also has really good workwear and outdoor gear, like good versions of Carhartt and Champion. The mosquitoes, ticks, and the brown-tail moths are really bad in Maine in the summer. I buy a combo of straight-up industrial-strength DEET and bug oil from Renys. I also load up on Comfort Colors T-shirts , which are native to Maine.
7:30 p.m: See a documentary at the drive-in The Shotwell Drive-In is part of the Camden International Film Festival, which my friend Ben Fowley started and runs. They started the drive-in during COVID, and it’s become the best part of the summer in Maine. They play a full mix of films. They played The Truffle Hunters last year for my 30th birthday. They do kids’ nights; they play a lot of documentaries. I have planned weekends around what’s showing at the drive-in.
12:30 p.m.: Get a chopped salad on Main Street My friends and I usually shop until we literally drop, so next we go across the street to Main Street Markets . It’s an elevated market and prepared-food takeout spot. I like getting an immunity salad , or if we want something heartier, we’ll go to Rockland Café . It’s an old-school seaside-diner vibe. I like to get scrambled eggs and sit at the tables outside and people-watch.
Day 4 8 a.m: Grab blueberries for back home Stop at Fresh Off the Farm , which is a little market in Rockport, to pick up strawberries, blueberries, Rainier cherries, a case of Maine Root root beer , and four giant bags of Little Lad’s popcorn to take on the road. I also buy Rock City Coffee’s Blueberry Coffee by the pound . You can grind it fresh there. We usually need to gun it back to the city to get to Hertz before it closes at 3 p.m.
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