Photography by Peter Tsai

Portlanders are of hardy stock, enterprising and independent by necessity and appreciative of the freedom that comes with living in New England’s northernmost state. Luckily for visitors, they’re a friendly, earnest bunch, too. The city of 67,000 is Maine’s largest and comes off as charming at all turns without trying too hard.

When you step into the lobby of the Press Hotel, you might not even realize you’re in a hotel. Up until 2009, this was the headquarters of the Portland Press Herald, Maine’s largest newspaper. As a writer, I appreciate this Autograph Collection hotel’s celebration of journalism, from the bold installation of vintage typewriters to the letters spilling across the carpet to the sentences from newspaper articles that line the walls. The Press Hotel has an equally strong commitment to local art, and if there’s anything Portland does well, it’s art and food.

Photography provided by the Press Hotel

Maine has a rich history in painting, textiles and woodwork that in recent years has been permeated with a contemporary panache. The Portland Museum of Art has a fine collection, including Winslow Homer’s maritime landscapes. For a look at emerging artists, visit the free Institute of Contemporary Art at MECA, the Maine College of Art. And a rotating exhibition space on the Press Hotel’s lower level highlights talented local artists.

Every touch at the Press Hotel is local, including turndown sweets by chocolatier Dean Bingham, accompanied by an anthology of Maine poetry on the nightstand. Visit Dean’s Sweets in the Old Port district to try uniquely Maine truffle flavors like Maine moonshine, Moxie soda and Needhams — a traditional coconut and mashed potato candy.

James Beard Award–winning Eventide Oyster Co. is just the tip of the iceberg when it comes to Portland’s eclectic dining scene. Fish and seafood are uniformly outstanding, as one might expect, from the flounder at neighborhood favorite Woodford F&B to the smoked mussels at Union. Evo Kitchen + Bar’s Middle Eastern–inspired small plates are inventive and outstanding, including signature sweet and spicy tuna crudo with Fresno chilies and baklava ice cream.

Photography by Peter Tsai

Hit the Road

As endearing as Portland can be, there’s so much more of Maine’s coastline to explore. Head south, and in less than an hour you’ll find yourself in the sleepy Kennebunks, where American traditions like Fourth of July fireworks and sparklers on the beach are cherished by locals and visitors alike. The Bush family has kept a summer residence on a private peninsula here for decades. Drive along Ocean Avenue to spot the estate, then trace the small town’s history from ship captains to presidents at the First Families Museum.

Quaint boutiques along Dock Square are worth sifting through for treasures like wild Maine blueberry preserves and colorful clutches made from recycled lobster bait bags. Get up at sunrise for an authentic taste of Maine living: watching fishermen unload traps at the Cape Porpoise lobster dock.

For posh accommodations and impeccable service, Grace White Barn Inn & Spa is outstanding. Colorful tulips and live music breathe vivacity into this elegant Relais & Châteaux property. Nature becomes both art and science across the fields, forests, dunes and wetlands of nearby Wells Reserve. Learn about the estuary ecosystem and wildlife haven at the ecology center.

Photography provided by Hidden Pond

For seclusion, Hidden Pond’s individual cabins across 60 acres of forest are enticing. Wild mushrooms and fiddlehead ferns you’ll taste at the resort’s restaurant, Earth, grow in the surrounding woods. Chef Justin Walker lives on a 17-acre farm nearby, where he harvests heirloom tomatoes and raises goats for milk to use in his hyper-seasonal cuisine.

At sister property Tides Beach Club, fall asleep to the sound of crashing waves. The historic inn is right on Goose Rocks Beach and features colorful rockers on the porch. A pair of signature oceanfront suites designed by Jonathan Adler boast whimsical nautical patterns and bright splashes of color.

Photography provided by Tides Beach Club

On the way back to Portland, spend a tranquil night at Inn by the Sea in Cape Elizabeth. Stop in Biddeford, a former mill town, on the way there for ice cream at Sweetcream Dairy. Inn by the Sea elevates eco-friendly luxury to the next level with a dozen two-bedroom suites. Indulge in a signature sea waves massage at the LEED-certified spa and feel like you’re underwater, being caressed by the ocean. Sea Glass restaurant doubles as an art gallery with an eclectic collection of regional pieces, from cheerful lobsters to Maine fish houses with an Asian landscape twist. Stroll down the boardwalk to Crescent Beach to catch the sunset while relaxing with a drink beside the cozy fire pit.