Historic brick buildings, a working waterfront, and award-winning restaurants: the first time I visited Portland I wanted to be able to call this city home, and now I feel lucky that I do. On this “staycation,” my husband, Sam, and I hit up old favorites and uncover a few new gems.

5:15 p.m. @ Portland Hunt and Alpine Club Still in time for happy hour, I grab a drink with a coworker. The James Beard- nominated spot rotates the cocktail specials depending on the season, and my colleague recommends the No Brainer. It’s made with gin, rum, lime, ginger, and soda, and is, exactly as billed, an “easy, refreshing” way to kick off the weekend.

7:30 p.m. @ The Press Hotel Located in the former Portland Press Herald building, the Press features a decorating scheme that is reminiscent of a deconstructed typewriter. The front desk’s curving woodwork recalls a row of type hammers, the staff wears round “P” letter keys upon their lapels, and carpeting patterned with typewriter font spills down the halls. There are also several site-specific art installations by local artists, such as Erin Hutton’s Swarm—a small tornado of typewriters that conjures up a nostalgic image of a newsroom that once was a flurry of activity.

8:15 p.m. @ Ebb and Flow My husband and I eat a lot of seafood, so we’re excited to try this Mediterranean spot from chef William D’Auvray and Nova Seafoods’s Angelo Ciocca. From a corner
seat in front of a large window, we feast on charred octopus, braised chicken soup, and skate sautéed in brown butter sauce, while watching people stroll down Commercial Street as evening comes to Portland.

10:15 p.m. @ Boone’s Fish House and Oyster Room Around the corner towards the Custom House Wharf, we stop in for what we think will be a quick, quiet drink—but we’re pleasantly surprised when it turns out it’s late-night happy hour with live music and half-off oysters.

9:00 a.m. @ The Press Hotel I meet up with the hotel’s friendly director of rooms, Ginny Petrovek, who gives me a full tour of the rest of the space, including meeting rooms and the downstairs art gallery, while my husband runs out to grab us breakfast.

10:30 a.m. @ Tommy’s Park Sam and I meet up to picnic on our favorite raspberry scones and lattes from the West End’s Aurora Provisions, and then we wander down to Maine Squeeze Juice Cafe, where I order one of the green smoothies that I’m addicted to.

11:00 a.m. @ Holly Hamilton Jewelry On our way back to grab the car we duck into this jewelry shop. The designer—classic and elegant in a polka dot top— makes everything herself. She mentions that she keeps something she calls “wish lists,” and I’m only too happy to participate, pointing out a pair of small diamond and gold earrings for a future gift idea.

11:45a.m. @ Bradford’s Rug Gallery Our French bulldog has been slipping on the hardwood staircase in our home, so we need to install a runner. Bradford Ross walks us through several rug options, but because our stairs have a bend, we set up an appointment for him to come by and take some measurements. While we’re there, we sift through his extensive, colorful collection of vintage Moroccan, Persian, and Oushak rugs.

1:00 p.m. @ Maria Antonieta Couture We were hoping to try Sur Lie for lunch but it doesn’t open until 4:00 p.m. on Saturdays, so instead, we pop into this clothing boutique. Maria, the designer and sophisticated seamstress, is just handing off a finished wedding dress to a beaming bride. “I write happy ending stories,” she tells us.

1:30 p.m. @ Old Port Sea Grill and Raw Bar We walk down towards the waterfront for lunch. Last summer, I was fortunate enough to attend a delicious Kennebunkport Festival Art of Dining dinner with a menu from the Old Port Sea Grill,
and I’ve wanted to go ever since. Our meal doesn’t disappoint—especially my tuna tartare, which I eat so quickly that Sam barely gets a taste.

2:45 p.m. @ Old Port We decide to do a little shopping and browse Attos By Design, where we admire gorgeous, glittering estate jewelry, then pop in next door to Folia, where the store owner, Edith Armstrong, sells her handmade pieces that are designed and created right there in the shop. We run across the street to Zane, which carries my favorite brand of denim. Next, we stop into Coastal Maine Popcorn Co., where we sample flavors such as horseradish dill, blue cheese, and kettle corn. We settle on three bags to ship to my dad, a popcorn fanatic.

4:40 p.m. @ Fiachre Sam and I browse the well-tended-to plants, cute selection of books, and moss-covered terracotta pots before settling on a huge, gorgeous fern that looks a little bit like Cousin It. The owner graciously offers to let us try it out first, so we run it home to see how it works. It’s a little too big for our front porch, but it adds the perfect amount of drama to our small, shaded back patio. We return to let her know it’s a keeper, and we wind up chatting long past her 5 p.m. closing time.

7:00 p.m. @ Piccolo An intimate dining room is the setting for our long, delicious dinner out with friends. We start out the evening splitting several apps, including the group’s favorite, peekytoe crab bruschetta, then spend the next several hours catching up over housemade pasta and good wine before heading back to the hotel.

8:45 a.m. @ Union We head downstairs to the hotel’s restaurant, where executive chef Joshua Berry is at the helm. We welcome the morning with omelets, fruit and granola, fresh orange juice, and ample caffeine. Then we check out, knowing we’ll be back to eat as well as recommending a stay to out-of-town friends.

9:45 a.m. @ Old Port We wander down to the waterfront and walk out on a pier, appreciating the up-close look at Casco Bay.

12:15 p.m. @ Zapoteca Restaurante y Tequileria We head to Shannon Bard’s excellent eatery for a late brunch. I order the Taco de Langosta Puerto Nuevo, which comes with duck fat sautéed Maine lobster served in the shell as well as the best Mexican street corn I’ve ever had.

1:30 p.m. @ Holy Donut There’s a line almost out the door, but it moves quickly and when we reach the front we order two of the potato donuts to go—dark chocolate sea salt and fresh lemon—before they sell out for the day.

1:50 p.m. @ Eastern Promenade We drive down to the Prom and find a patch of grass. Victorian houses line up behind us in an elaborate parade of gingerbread trim, turrets, and fish-scale shingles. Diamond-shaped kites sway in the sky and sailboats with full jibs glide through the bay in smooth, slow motion. We’re so very well fed and have a gorgeous view: it’s a perfect Sunday afternoon in Portland.

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