Tasha Graff, 38, lives in Portland, and has been teaching high school English for 17 years. She just finished her tenth year at South Portland High School. A graduate of Bowdoin College, she has a master’s degree in English literature from Middlebury’s Bread Loaf School of English and a PhD in public policy from the University of Southern Maine.

Even in the summer, my day begins at teacher time, just after sunrise. I lace my sneakers and leash my dog Lulu, a very good girl, and we climb Munjoy Hill via the Fort Sumner Park trail, which curves upward through such verdant trees that for a brief moment you’re lost in a forest. We emerge at the park and turn around to gaze down at the rooftops of Portland and, in the distance, Mount Washington.

A perfect summer vacation day for teacher Tasha Graff starts with a climb to Fort Sumner Park on Portland’s Munjoy Hill. Ben McCanna/Staff Photographer

We walk along the Eastern Promenade as Casco Bay sparkles, on the lookout for Lulu’s best four-legged friend, Shady. Then it’s time for a delicious breakfast sandwich and iced beverage from Coffee ME Up before a trip to Print: A Bookstore for a new book. Lulu can’t read the sign on their door that says “Dogs Loved,” but she knows she’ll be greeted by name and plied with treats, and thus wags her tail whenever I say, “Bookstore?” Back home in our yard, I read while Lulu snoozes.

After a few chapters, I text a few friends and call Bánh Appétit and order us five of their amazing bánh mì sandwiches for a picnic lunch. Jason honks in the driveway, and we head west to pick up Nurse Kate, and then north to Bath, where we find Sophie and Max on the shore of the mighty Kennebec River.

We drive to Phippsburg together and, armed with provisions and bug spray, hike Morse Mountain. We eat on Seawall Beach while Nurse Kate, the mermaid among us, swims, no matter the weather or tide; the rest of us sensibly dip our toes.

We meander northeast to Belfast, where Sophie and I explore another favorite bookstore, Left Bank Books, Jason and Max source coffee at Downshift, and Nurse Kate grabs treats at Chase’s Daily. We walk along the harbor and pick our favorite quirky boat names.

The Sprague River meanders through a marsh at Bates-Morse Mountain Conservation Area in Phippsburg. Ben McCanna/Staff Photographer

We drive back to Portland in time to grab a bottle of wine at Micucci’s Grocery before catching the ferry to Peaks Island for wood-fired pizza at Il Leone. We sit on the picnic benches at the Lions Club, admiring the resplendent skyline of Portland across the bay. As the sun sets, the teacher and timekeeper in me re-emerges, and I herd my pals back to the dock just in time to catch the ferry home.

Our last stop is Night Mares – because it’s vacation, after all, so there must be room for dessert – and we share a slice of cake and a nightcap. It’s time for bed, but not before one final toast, this one to Portland: Goodnight, you princess of Maine, you queen of New England.

Il Leone’s L’estate pizza. Ben McCanna/Staff Photographer

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