Nestled along Maine’s rocky coastline, Portland is the kind of place where lobster rolls and lighthouses live in perfect harmony. It’s walkable, artsy, and full of charm making it ideal for a long weekend escape. Whether you’re wandering cobblestone streets, hopping between boutiques and bakeries, or sipping something crisp by the waterfront, Portland delivers.
Eventide Oyster Co.
This modern oyster bar is a must. With rotating local oysters, brown butter lobster rolls, and inventive small plates, Eventide brings the freshest flavors of the Atlantic to your table.
Tandem Coffee + Bakery
Housed in a converted gas station, Tandem is known for its biscuits, clever breakfast sandwiches, and the kind of coffee that makes you cancel your afternoon plans just to stay a little longer.
Central Provisions
A cozy, buzzy spot in the Old Port serving inventive small plates and killer cocktails. Go early, they don’t take reservations, and it’s always worth the wait.
The Press Hotel
Set in a former newspaper building, this boutique hotel blends historic charm with modern luxury. Every room is thoughtfully designed, and it's just steps from the Old Port.
Blind Tiger
An elevated bed and breakfast housed in a stately mansion. It’s quiet, stylish, and full of personality. Perfect for travelers who love a touch of home with their hotel.
The Francis
A beautifully restored 19th-century mansion turned modern stay, with a wellness spa and a local feel that fits right into Portland’s relaxed pace.
Walk the Eastern Promenade
This scenic waterfront trail offers sweeping views of Casco Bay. Pack a snack and watch the sailboats glide by or hop on a ferry to a nearby island.
Visit Portland Head Light
The most photographed lighthouse in America and for good reason. Located in nearby Cape Elizabeth, it’s the definition of postcard-perfect.
Explore the Arts District
From the Portland Museum of Art to indie galleries and bookshops, this area is bursting with creative energy. Don’t miss First Friday Art Walk if you’re in town.
When you're hopping from coffee shops to coastlines, the Teddy Pouch is your low-maintenance, high-style travel companion. With its extra-wide zip and soft structure, it’s ideal for holding sunscreen, lip balm, Polaroids, or whatever you grab from the farmer’s market. Whether tucked into your tote or tossed into your carry-on, it’s the little luxury you’ll be glad you brought along, just like your trip to Portland.
