Portland is the kind of city that rewards a little wandering. Great food, independent shops, art, the working waterfront, and plenty of places to slow down are all within easy reach. With The Longfellow as your home base, here’s how we’d spend a perfect weekend in our little city by the sea.
Friday: Settle In
Arrive Friday evening, drop your bags, and settle into your room before making your way downstairs to Five of Clubs. Start the weekend with a cocktail, a glass of wine, or a few oysters, then walk across the street for your reservation at Wayside Tavern, one of our favorite neighborhood spots.
After dinner, there’s nowhere else you need to be. Head back to The Longfellow, slip into a robe, climb into bed, and settle in for what just might be the best sleep of your life.
Saturday: Shop, Eat & Explore
Wake up Saturday morning and make an early stop at Tandem Coffee + Bakery next door. Pick up a coffee and something freshly baked before the line gets too long, then set off toward downtown.
Start along Congress Street with a visit to Bold Magazine Shop and Soleil before making your way toward the Old Port. From there, spend the morning browsing some of our favorite local shops: Viand Mercantile, Blanche + Mimi, Sherman’s, Zane, and Baske, with plenty of room to stop anywhere else that catches your eye along the way.
By now, you’ll probably be ready for lunch. Make your way to Eventide for oysters, crudo, and their much-loved brown butter lobster roll. Not a seafood person? Their burger is very much worth ordering, too.
From here, the afternoon is yours.
Stay downtown and visit the Portland Museum of Art, right on Congress Street, for a few leisurely hours among its collection. If you’d rather get outside, take a short drive to Portland Head Light for one of Maine’s most iconic coastal views. Or make your way back to The Longfellow and spend the afternoon unwinding with a signature massage or infrared sauna session at Astraea Spa. Whatever strikes your fancy, Portland has it.
As evening arrives, get ready for another very good Portland meal. Our car service can take you downtown for dinner, and narrowing down the options may be the hardest decision of the weekend. A few favorites: Fore Street, Scales, Leeward, and Izakaya Minato.
And if you’re not quite ready for the night to end, head back toward the hotel and slip into Bramhall, the cozy speakeasy bar just across the street, for one last drink.
Sunday: One Last Slow Morning
There’s no need to rush Sunday morning. Join us from 9–10 a.m. for a complimentary yoga class in The Longfellow fitness center, then make your way downstairs to Twinflower Café.
Settle in with coffee, a smoothie, and a wholesome breakfast; the kind that leaves you feeling ready for the journey home.
When it’s finally time to leave Portland behind, the weekend doesn’t necessarily have to end. If you’re heading south, take the scenic route and stop at a few of the antique shops scattered along Route 1. You never know what you might find, and an old Maine treasure makes a fitting final souvenir.
Of course, part of the pleasure of a weekend in Portland is leaving a little room for spontaneity. You’ll spot another shop, hear about a restaurant you have to try, linger over lunch longer than expected, or simply find a place you’d like to stay awhile.
That’s part of the fun. Stay awhile, wander often, and make the weekend your own.