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Want to give your love life a shot in the arm, figuratively speaking? One word: Portland. (You were expecting Paris? Get real.) Part of this recommendation is sheer sentimentality: The gorgeous, laid back Pine Tree State has been the backdrop of much of our romantic history, including sailing trips, country inn and hiking excursions, and assorted kissy-face getaways with our significant others. And Portland has an added benefit, an excellent dining scene. So even if the romance doesn’t sizzle, you’ll have had a great meal or two. Portland in winter may not ring everyone’s romantic chimes, but we set out to see if the city could work its mushy magic on a couple of bedraggled souls who haven’t had a haircut since February 2020. Current travel restrictions require a current COVID test prior to going, or a spell of quarantining. Is this destination worth a shot, literally? Read on.

Creative COVID dining, Portland-style


Portland has an ace up its sleeve this winter: outdoor dining. If you miss fine dining, and the indulgence of being served luscious food (as opposed to reheating it in the microwave), consider the outdoor chalets at Evo Kitchen + Bar (www.evoportland.com). This Old Port standby for modern Mediterranean fare has installed five heated chalets. You can book one for your party of two to four, and settle in to your own private, atrium-like “dining room,” with a heater, wood floor, even a chandelier and candlelight. Spring for the 10-course chef’s tasting menu, and get ready for a memorable meal (tweaked nightly, depending on what’s fresh). On the night of our visit, courses included cauliflower soup with Parmesan custard (fabulous), chickpea fries (deep-fried clouds of deliciousness), citrus-spiked chicory salad, scallops with salsify, pancetta, and pomegranate seeds, plus salmon, duck breast (with a lovely apricot-soy sauce and grilled endive), and beef strip loin. Sorbet and an airy Pavlova provided a sweet finish.

As an alternative to indoor dining, Portland’s Evo offers multi-course dining in a private chalet.
As an alternative to indoor dining, Portland’s Evo offers multi-course dining in a private chalet.Diane Bair for The Boston Globe

This is a spendy meal, but it’s a great choice if you want to splurge after months of DIY cookery. And remarkably — considering it was 28 degrees outside — the little heater kept our chalet toasty warm. Plus, we were dressed for the occasion — layered up in long johns, fleece, down, and wool. We saw a few more-fashionable souls on the streets of Portland that night, tottering around on heeled boots and sans headgear, but their grimaces said it all. If there’s ever a time to pull out the L.L. Bean everything, it’s a winter date night in Portland!


We’d planned to check out the hot chocolate and s’mores board at The Yard bar (www.yardportland.com) in East Bayside, but not after 10 courses! And so, we waddled back to our home for the night, the Press Hotel (www.thepresshotel.com). Portland has no shortage of nice places to stay, from inns to Airbnbs to hotels, but we liked this one in the Age of COVID Besides the appeal to our writerly selves (it’s set in the former home of the Portland Press Herald newspaper), this 110-room property is part of Marriott’s Autograph Collection. We felt safer staying in a hotel with standardized safety protocols in place, like this one — and given the post-holiday time frame, there were few other guests booked. We loved the Press Hotel’s newspaper-y touches — antique typewriters placed throughout the property, wallpapered “headlines “in the hallways, and typeface-printed carpet. Not sure about the romance side, but this spoke to our love of journalism and the written word!


And it’s fun to stay in Portland’s Old Port district. The shops lend a lively vibe, even off season. We popped in and out of the galleries, noticing few other customers and occupancy limits in place. Prowling around, we discovered that Deering Oaks Park is open for ice skating. Ice skating, mitten-in-mitten is so romantic. Alas, we didn’t have skates stashed in the car, and didn’t see any rental options nearby, but it was a festive scene nonetheless.

Lobster and lighthouses (but of course)

But like most Maine tourists, we were focused on two things (besides love): lobsters and lighthouses. Yes, even in winter! And so, we added a few more layers of clothing and set out to find them.

It didn’t take long. We’ve used DIY lobster roll kits from Luke’s Lobsters (www.lukeslobster.com) at home, but were delighted to discover their flagship restaurant at Portland Pier. Eschewing the restaurant’s indoor tables, we headed to the outdoor deck facing the ocean. Diners can choose a bench alongside one of two fire pits, or nestle closer to the restaurant at an outdoor table on the balcony. It felt positively celebratory to tuck into our lunch outdoors, in view of sparkling Casco Bay, on a winter’s day. The clam chowder added a warming touch (tasted good, too), and the lobster rolls are terrific — served on buttery grilled rolls, with the lobster meat lightly dressed and drizzled with more butter. Luke’s offers outdoor service all day from Thursday through Sunday, with drink specials and $3 chowder. “Real Mainers are tough and love the cold. It has been a great success so far and we look forward to providing hot food and beverage for the rest of the winter season,” says general manager Allie Edmund.


Outdoor dining continues in Portland. This couple was at Luke’s Lobster.
Outdoor dining continues in Portland. This couple was at Luke’s Lobster.Diane Bair for The Boston Globe

Next up, lighthouses. For the perfect local twofer, we recommend this: Hang out in Portland for food and drink, and head to nearby Cape Elizabeth, a short drive south, for outdoorsy stuff. Folks flock to Fort Williams Park and Portland Head Light (www.portlandheadlight.com) to hike along the sea cliffs when summer breezes sweeten the air. In winter, it’s a worthy (if windy) jaunt, provided you dress in your finest polar wear. We noticed lots of dogs and their people; there’s a wide-open area for canines to run unleashed. Bonus points for Goddard Mansion, an oceanfront ruin that’s just begging for some HGTV TLC. As for romance: Well, there’s nothing more romantic than your walking buddy offering you his beanie when your ears get cold.

A lighthouse, lobster, and a fancy meal — and that was only our first half-day. Given that we’d undergone COVID testing to make it happen, we were determined to squeeze out as much fun from our trip as possible. We started Sunday with a trip to Holy Donut (www.theholydonut.com) on Park Avenue for a couple of Leigh Kellis’s famously dense-and-delicious potato-based doughnuts. And then we drove back to Cape Elizabeth for more hiking-with-a-view, at Two Lights State Park (www.maine.gov).


Named for two lighthouses located outside the park (at the end of Two Lights Road), this 41-acre park sits on the rocky headlands of Casco Bay and the open Atlantic. Picnic tables (amazingly, in use in winter by hardy Mainers) and park benches dot the property, but you’ll likely want to keep moving, to take in the views and to keep warm. We didn’t see crowds of people, but there were a few couples out and about, taking advantage of the sunny day. We could’ve stayed for a while, watching the waves crash over the rocks, but we had one more stop to make before heading back to Massachusetts: Sea Glass Restaurant (www.seaglassmaine.com), at the Inn by the Sea. Those lobster rolls weren’t going to eat themselves!

At the Press Hotel, the former home of the Portland Press Herald, decor includes antique typewriters and cool details like headline-printed wallpaper.
At the Press Hotel, the former home of the Portland Press Herald, decor includes antique typewriters and cool details like headline-printed wallpaper.Diane Bair for The Boston Globe

The restaurant at this seaside resort is a great choice for those who want tasty fare and good service, but don’t want to commit to indoor dining: They’ve got heat lamps, fancy fire pits, and wool lap blankets to up the comfort quotient on their al fresco deck. We even took our coats off during lunch — that’s how warm it was — the better to dig into our lobster roll and the restaurant’s signature fries. These chubby fries are dusted with sugar and spice and are totally irresistible. If you get only one order, you’ll be fighting for every last wedge. Or feeding each other fries, since this is a romance story.

And that’s how you do Portland in winter. Admittedly, we missed some cool haunts, like the Portland Museum of Art (www.portlandmuseum.org; currently closed due to COVID-19) and the lovely Italianate Victoria Mansion (www.victoriamansion.org.; closed for the season), not to mention the myriad summertime boat cruises, and leisurely neighborhood strolls around Munjoy Hill and East Bayside. But we felt like we had a mini-vacation, even with “coastal distancing” in place, as the Inn by the Sea’s Rauni Kew dubs it. Lobster, lighthouses, and a little romance; that’s a lot to love in 24 hours.

If you go: www.visitportland.com; www.visitmaine.com.