Drum roll please… here are all our Portland, Maine recommendations (as locals) in one blog post!

We feel incredibly lucky to call Portland, Maine home.

Not only is it one of New England’s most beautiful coastal cities, it’s also a place people travel to intentionally - to slow down, reconnect, and experience stunning natural beauty and authentic culture.

Over the years, we’ve worked with many clients who visit Portland for a photo session with us & then stay a few extra days to explore the city- which we highly recommend!

Hence, we’ve created a full list of recommendations here for anyone thinking of visiting…

If you’re planning a trip, here are some of our favorite places to stay, eat, drink, and explore, plus a few ideas you might not have considered.

Where to Stay in Portland, Maine

Whether you’re looking for something modern, artistic, or cozy, Portland has no shortage of incredible places to stay.

We often recommend:

Canopy by Hilton – Stylish, modern, and right by the waterfront
The Pomegranate Inn – A colorful, art-filled boutique stay in the West End
The Press Hotel – A beautifully restored historic building celebrating Portland’s creative culture
The Inn on Peaks Island – Perfect if you want a quieter, coastal island experience

Or, if you want something more personal, browsing Airbnb can lead to some truly unique stays.

Where to Eat (A few Local Favorites)

Portland is known for its food scene (and for good reason!) The city blends maritime tradition with a creative, modern edge, offering everything from seafood to globally inspired cuisine.

A few favorites:

Via Vecchia - Chic Italian eatery offering brunch staples, small plates, seafood & steak, plus wine & cocktails.
The Honey Paw - Bright, contemporary bistro offering Asian-inspired noodles & other bites with local craft beer.
Fore Street - This rustic spot's open wood-fire grill, oven & spit lend smoky flavors to upscale American fare.
Lunchonette- Eclectic luncheonette with iconic storefront in Portland, ME serving breakfast, lunch and more.
Highroller - Lobster rolls & other seafood in a neighborhood diner that sources local brioche rolls.
Tandem Coffee Roasters - Espressos, pastries & retail bags in cozy cafe with brick walls, open roasting space & cuppings.
Mami - Food truck turned brick-&-mortar serving Japanese-style street food in a lively, comfortable space.
Sichuan Kitchen - Unpretentious dining space serving up traditional Sichuan fare, including pork buns & beef noodles.
The Shop - Buzzy oyster market with a dine-in raw bar for fresh shellfish, wine & beer plus a seasonal patio.
Bread and Friends - Bakery and restaurant specializing in naturally leavened breads, artisan pastries, and elevated sharing plates for brunch and dinner. Complemented by a coffee program as well as thoughtful wine, aperitif, and beer selections.
Terralingua - Inventive takes on BBQ & Southwestern dishes are served in a homey space decorated with pale wood.
Norimoto Bakery - Offers unique handmade baked goods with Japanese flair made-from-scratch, daily.
Street & Co- cute and cozy setting right on Wharf St. with really, really good seafood.

Whether you’re planning a nice dinner or casual bites, it’s hard to go wrong here. And this only scratches the surface of all the incredible food the city has to offer. It’s truly a foodie’s dream.

Where to Grab a Drink

From cozy coffee shops to lively cocktail bars:

Blyth & Burrows - Vintage-inspired cocktail bar with a maritime theme serving house cocktails & upscale small plates.
Bramhall - Dark, basement speakeasy with inventive comfort food, local beers & an extensive bourbon & rum list.
CBG - Down-to-earth bar & grill furnishing comfort food with a twist in unpretentious surroundings. Plus a subtle Big Lebowski Theme.
Bissel Brothers - Local craft brewery featuring a bustling warehouse like taproom with indoor & outdoor seating. A Maine beer staple.
Arcadia - Arcade, console, pinball & board games entertain the patrons at this bar with beers & some spirits.
Low Key - A combo soft serve shop and bar in the East End. Incredibly cute and cozy interior with hightop seating, with minimal outdoor seating.
Smalls - Warm, easygoing hangout with coffee, cocktails & light bites, plus locally made products for sale.
Arabica - Compact, welcoming coffee shop serving locally roasted beans & fresh-baked pastries. They make incredible lattes, too.
Uncharted Tea - Cozy cafe for bubble tea with many milk and sweetener options, along with board games.

Portland’s drink scene is relaxed, creative, and full of personality- just like the city itself.

Things to Do & Explore

One of the best parts about Portland is how much variety you can experience in a short time. Almost everything listed is within a 10-15 minute radius!

Must-see spots:

Eastern Promenade – sweeping ocean views and peaceful walking paths
Mackworth Island – a quiet escape just outside the city
Peaks Island – accessible by ferry and perfect for biking and exploring
Fort Williams Park – home to iconic coastal views
The Audubon - beautiful nature preserve with trails just outside of Portland

You’ll also find:

Beaches all along the coast
Vintage shops and boutiques
Farmers markets and local events
A multitude of music venues (like Thompson’s Point & beyond)
A thriving arts scene, including the Portland Museum of Art
Tons of local breweries with amazing craft beer selections.

Portland blends outdoor adventure with culture in a way that feels easy and accessible.

A Different Way to Experience Portland

Many of our clients travel here not just for the scenery - but for the experience of being photographed in a way that feels empowering and transformative.

At Jen Dean Photography, our bespoke photo sessions are designed to be more than just photos. With over 25 years of experience, our work focuses on helping people feel seen, comfortable, and connected to themselves.