Maine out of season is unmistakably a great destination: hospitable, good-humored, plenty of elbow room, short days, dark nights of crackling ice crystals.
— Paul Theroux

Portland is fantastic, it totally took us by storm! It's tiny but amazingly inspiring and interesting. We went in November, when streets were half empty and winds freezing. But if you're smarter than us, then you'll go during summer - when the town springs to life. Portland is the artist's, hippie's, hipster's, foodie's and fishermen's dream alike. Did we mention it's small? You'll know your way around after only a couple of days. Nonetheless it has a ton of places to explore. It has a industrial, hip feel, tons of culinary gems and a beautiful oceanside location. We were lucky to meet up with a couple of locals here, who gave us great tips on where to drink and eat. We hope that you'll enjoy these tips as much as we did.   


Fore Street: Fore Street is a real destination restaurant at this point and has been for several years, The food is creative and locally sourced for the most part. This is one of the top 3 restaurants that we have ever visited. The menu changes daily and the intimate atmosphere and amazing service made this an experience to remember. Try the wood grilled hanger steak with cipollini onions and the wood oven roasted whole fish.

Duckfat: Duckfat is a small sandwich shop that has it all: classic Belgian fries made with local Maine potatoes fried in duck fat, panini, soups, salads, charcuterie, sodas and milkshakes all made in house. Try the duck confit panini with pickled Maine apples and herb mayo and add a side of Belgian Fries with toasted curry mayo and lemon-herb mayo.

Eventide: The day's oysters and shellfish are displayed on a piece of granite at the end of the bar. Get an assortment of local oysters and add some tabasco or kim chi. Another favorite here are the fried oyster buns. Cornmeal-crusted oysters, creamy tartar sauce and pickled red onions - all tucked into a sweet steamed bun. You have to try the lobster roll - a roll stuffed with lobster and a choice of house mayo, hollandaise or brown butter vinaigrette.

Central Provision: This place is a great place to have lunch or dinner. The menu is inspired by global cuisines, and executes it beautifully. The bar keeps up with the creativity of the kitchen. They have an awesome inventory, and great cocktails. Go here if you want to have a unique experience. 

Otto’s: The best pizza in Portland. Small hole in the wall place with locals queuing up outside. Go here for a quick lunch - you won’t regret it.

Hugo's: houses one of Portland’s most innovative menus. When entering the rustic East side space, you'll see a modern, open kitchen tucked behind a spacious bar. The menu consists of tasting menus only, with or without wine pairings. Choose from 'Foraged & Farmed', 'From the Sea' and 'Forest & Field'. Whatever is your choice, you are sure to experience a night of seasonal, Atlantic-inspired molecular gastronomy.

Fore Street

Fore Street

Duck Fat

Otto's Pizza

Central Provisions


The Holy Donut: There are few donut places better than this in the world.  While they only have about 10-15 flavors, they are all excellent.  Who needs to engage in a paradox of choice when you can sink your teeth into a Dark Chocolate Sea Salt donut or a Maple Glazed? 

Bard Coffee: The local favorite. Bard coffee serves up great coffee as either pour-over or espresso. Go here before strolling around Portland to charge your batteries.

Tandem Coffee Roasters: More than half of the small warehouse housing Tandem Coffee Roaster is dedicated to roasting - lovely award winning coffee - which leaves only a small, intimate space for coffee thirsty guests to sit. A few stools dot the bar, but that's what makes this place so special. Its design is minimal and its coffee fantastic. An instant hit after its opening in 2012.

Coffee By Design: this is Portland’s “old guard” coffee roaster. A traditional, locally-roasted, community-friendly, not too hipster but still utterly cool place that fits perfectly to Portlands laid-back atmosphere. Their coffee spectrum is broad, and they house some delicious beans. Head this way for an authentic, small-town experience.

Speckled Ax: Speckled Ax is a practitioner of wood-fired coffee roasting, a method that purportedly provides a whole host of benefits. Their narrow and stylish downtown cafe is a great place to let freezing winter winds pass outside, while having a warming cup of coffee. Choose between “fast coffee” if you're on the run, or wait for a hand-poured drip.

Holy Donut

Pomegranate Inn


Portland Trading Company: Portland Trading Co. is simply a general store for modern times. The store covers both Men's and Women's clothing, accessories, footwear, apothecary, and homegoods. In addition, they cover a well-curated collection of all things vintage: wares, homegoods, books and unique items. A must go-to if you visit Portland and want to buy something special to bring home.

Chellis Wilson: This place is more art installation than conventional shop. The space, small and sunny with a tin ceiling and ebony floors, is tucked away on a quiet side street and filled with a spare and carefully arranged selection of clothes, books, textiles, and furniture.

Eco Home Studio: a store, a destination, a design resource, whose stock consists of products made from recycled materials or products created using sustainable practices.

Bliss Boutiques: offers a great range of designer women clothing. Explore racks of adorable dresses and stacks of jeans, sweaters and lingerie and lots of other must-haves. You'll find its brick and mortar location in Portland Maine's historic Old Port.

Homegrown Herb & Tea: We love tea. And any intimate, high quality, family run tea shop especially! This place is spot on. Sarah Richards quit teaching Spanish to open her store at the foot of Munjoy Hill. She grows and dries herbs and flowers at her family farm in New Sharon and around her house in Portland. From her workshop behind the counter she concocts custom herbal blends to boost health and balance.

Portland Dry Goods Co: a gentleman's dream. Find beard wax, combs and high quality designer clothing. Among the brands they stock are; Engineered Garments, A.P.C., Wings + Horns, Seawall, Gant, Red Wing, Barbour, Stutterheim and Fjällraven. As hip as it gets guys! 

Home Remedya custom home décor showroom offering furniture, window treatments, designer rugs, fabrics, design consultation, custom sewing, and re-upholstery services. Maybe not the smoothest items to drag home after a quick weekend stay, but nontheless an inspiring and beautiful store.

Portland Trading Co.


Pomegranate Inn: We really enjoyed our stay at the Pomegranate Inn. Located in a quiet and easily-walkable neighborhood, the Inn featured delicious food, attentive managers, and eclectic decor. Kaitie's breakfasts were divine, and we appreciated the advice on restaurants nearby for other meals, too. We loved coming back to the fireplace to warm up in the evenings.

Danforth Inn: This inn is a luxury inn, much like Pomegranate Inn above. It's situated a little off the city centre which makes it feel like a little retreat. The inn is elegant and provides you with real comfort and warmth as it's very homely. A great place to stay when visiting this lovely harbour town.

Pomegranate Inn

Ollie enjoying breakfast at Pomegranate Inn


Navigate the city with our Google Map. We've pinned all of the places in our guide to the Google Map below. Simply go to the map when you're online to find your way around the city. If you don't have wifi when you're walking around the city, just make sure to load this map when you have access to wifi (at your hotel or at a café) and you'll be able to find your way around even if you're offline.

Our Portland photo gallery