It’s always nice to have an “insider” guide you about where to go, what to see, where to eat and where to stay when you visit a destination. Here, we’re lucky enough to have Libby Margolis-Pineo advise us about three great places to stay on her home turf, in Portland, Maine. 

Cocktail with a (rainy) view at Top of the East at the Westin Harborview.

Portland, Maine: Where To Stay?

Experience the best this little seaside gem has to offer by staying at one of the delicious in-town options we explore here. It’s an easy walk to the Portland Museum of Art, galleries, boutiques, hip coffee shops and more. Check out our First Friday Art Walk. Stroll the city, visit a brewery, sip creative cocktails, or knock back a few oysters. Explore our legendary restaurant scene, Bon Appetit’s Best Restaurant City 2018. No matter your passion, these three centrally located hotels have the charm, flavor and romance you crave.

Outdoor courtyard cocktails and dining at Port Harbor Hotel. 

Port Harbor Hotel in Portland, Maine

Serious research begins at the Portland Harbor Hotel, a snazzy boutique hotel with crisp nautical decor and an upscale welcoming vibe. Thoughtful contemporary touches include multiple charging stations and lighted makeup mirrors. Down to the last convivial detail, this hotel nails it.

Enjoy a nautical and nice room at the Port Harbor Hotel. Photo courtesy the Port Harbor Hotel.

After a great night’s sleep, guests wake in the heart of the Old Port within walking distance of shops, restaurants, galleries and working waterfront. Our little utopia of red brick, cobblestone streets and salty breezes has enough charm and soul for locals and visitors.

Maine-native executive chef Gil Plaster sources local fish, meats, artisanal cheeses, breads, farm-fresh eggs and dewy produce for the hotel’s BlueFin North Atlantic Seafood restaurant. Take a seat in the leafy garden courtyard for townie favorites like Fisherman Ravioli filled with herbed ricotta, catch-of-the-day seafood and salty Pecorino. Add a glass of Sancerre for a lovely pairing.

Ravioli, the Catch of the Day at Blue Fin in the Harbor Hotel.

Lobster ‘Scargot is simplicity itself, local lobster in garlic butter and herbs, escargot-style, rich and delicate — Maine lobster made easy.  Or enjoy Bluefin Tuna Crudo, served over crunchy greens with ponzu vinaigrette and roasted peanut crumble. Not a seafood fan? Savor the pistachio-crusted rack of lamb with a plummy glass of Zinfandel. With herbed fingerling potatoes, roasted root veggies, fennel and fig molasses, it’s robust, complex, rich and delicious. Full disclosure: we gnaw the bones.

Wind down with Maine blueberry ice cream or a rich affogato — vanilla gelato “drowned” in a shot of hot espresso, poured through a graphic chocolate swoosh. Nice!

East Meets Westin in Portland, Maine

Isn’t it romantic? The venerable Eastland Hotel, now the Westin Harborview, was the site of our first date. Handsome hubby and I head to the Top of the East resto-bar to reacquaint ourselves with panoramic views of Portland and Casco Bay. Wow! Even in a light rain, Top of the East still offers the best bird’s-eye view of Portland. We sip a specialty cocktail, Rosy Cheeks, of vodka, Lillet, lemon, rhubarb, rose water and a sprinkling of rose petals. We admire the art museum and Portland’s lovely brick architecture. Beyond historic slate rooftops, there’s dreamy Casco Bay in the distance.

Oysters served at Top of the East. Photo courtesy Top of the East.

We savor oysters on the half shell with delicious rhubarb gelée and strawberry mignonette — a perfect pairing with our slightly naughty Rosy Cheeks cocktails. We lazily discuss what has changed in this misty bird’s eye view over 30 years — not much.

We linger over Salmon Crudo in fennel gazpacho topped with tarragon sorbet. The scallops are briny and sweet; the sorbet is unctuous. With a French Quarter cocktail of gin, absinthe, bitters and Prosecco, it’s a wonderfully decadent pairing. Courtship continues with duck pastrami on petite rye crostini with red cabbage slaw and whole grain mustard. This is glam gourmet game-day fare — heavy on the romance, pretty-in-pink and dressed to kill. Major artistry in one blushing bite; kudos to the chef.

Flirtation concludes with two forks and lemon pistachio cake with key lime “dots,” Italian meringue twirls and pistachio sprinkles. This delectable modern art for two is paired with a mysterious Emerald City cocktail of rum, green tea matcha and mint. Magic!

As we transition from fascination to fling, there is only one thing left to do — get a room.

Harborview’s palette of beige and chestnut oozes masculine charm. Onsite spa Artné soothes and pampers with treatments for women, men and couples. With a dramatic renovation in process, I suspect contemporary flourishes will be arriving soon. Until then, views of Portland’s skyline and trademark red brick are wondrous, spectacular.

Vive la romance!

Regency Rules in Portland, Maine

In the heart of the Old Port is another historic gem, The Portland Regency Hotel. The venerable Regency occupies the historic Maine Armory, built in 1895. The neo-classical brick and stone exterior is carefully preserved. Original design elements like turrets and multi-faceted windows add charm and character to interior spaces.

Invited by the National Trust of Historic Preservation to become a distinguished member of Historic Hotels of America in 1990, The Regency is also designated an Environmental Leader — major kudos to the Regency from Planet Earth!

An old postcard shows what the Regency looked like in the past.

Classic comfort meets old world charm in rooms and suites with comfy beds and marble bathrooms. Each morning, coffee and newspapers are delivered right to your door — nice touch. Regency also has a fitness center and spa, with good news for townies: you don’t have to be a hotel guest to join the fitness center or book a massage.

One of Portland’s best-kept secrets is the Garden Café, a shady green oasis in the heart of the city. Across from the hotel entrance, it’s a quiet, grassy paradise of bistro tables and umbrellas, surrounded by lush green and flowers. Lights twinkle in the trees. In the heart of the Old Port and blocks from the working waterfront, this café feels miles away.

Starters and small plates include Maine crab cakes with black bean-corn salsa, and a creamy lobster stew with abundant lobster and hint of sherry. Local meets eclectic in a lobster, mango and avocado salad, a surprisingly “cool”combination of tastes and textures — ultimate summer-grazing, and so refreshing.

Chef Allen’s seared scallop with bacon, pineapple and jalapeno-pineapple reduction is a delectable star on the summer tasting menu. Savor the salty, sweet and briny scallops under the trees in this urban sanctuary — it will be a highlight of your summer.

For hearty appetites, don’t miss the Piedmont Burger with farm fresh egg, both locally sourced on the inn’s 100-acre farm in Cumberland. Not only delicious, this burger brings rewards like low fat and cholesterol. My body thanked me after eating this robust and tasty dish. And do leave room for dessert — the Maine blueberry crisp had me at hello.

I vow to return to the Garden Café throughout the season to enjoy one of Portland’s loveliest and best-kept summer secrets.

Epicurious travelers like me will be delighted with any of the three downtown doyennes I have explored. Each offers a combination of water views, creative cuisine, local sourcing, thoughtful service, central location, contemporary touches — and most importantly, a great night’s sleep — for a memorable and restorative getaway. Whether you want to step back in time or step into romance, these hotels have salty charm and history to spare. Relax and recharge for an overnight, long weekend, or my favorite — a townie staycation.

— Story and photos by Libby Margolis-Pineo except where noted.

To read more about Libby’s recommendations for where to stay in Portland, Maine, visit her full article on her site, EpicuriousTravelers.com.

Hungry for more? When Portland received the 2018 Best Restaurant City award, Libby recounted some of her favorite restaurants in her home town, and shared a great recipe from one of them.

Pin this tips to Pinterest so you don’t forget them – or get lost!