Eat Your Way Through Portland, Maine: 5-Day Itinerary

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  • Outdoors

  • Coastal

  • Foodie

white lighthouse next to body of water
Fora’s Take

There is no destination like Portland, Maine. This coastal locale has beaches, mountains, stunning islands, the freshest seafood from award-winning restaurants – all in a beautiful, easily walkable port town with great history. The people are beyond friendly, and Portland is simply magical.

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Where to stay

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Press Hotel

Writerly retreat in a former printing press, and home to one of Portland’s best restaurants.

Portland Harbor Hotel

In the busy Old Port neighborhood, a light-filled boutique hotel with a maritime style and popular restaurant.

Portland Regency Hotel & Spa

Expect a historic look and vibe, a fun lounge bar, and a heart-of-the-action location in the Old Port.

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Day 1: Your first taste of Portland

aerial view of buildings next to body of water

Fly into PWM and check in at the Press Hotel, which is equipped with a shuttle for extra convenience. The Press Hotel is one of our favorite accommodations, but find a Fora Advisor to chat about different options.

First, coffee

Portlanders love their coffee and are proud of the fact that most of the coffee shops in the city are independently owned. Enjoy your first cup at Bard Coffee. The owners are local and fantastic, and their brew is certified organic.

Go kayaking

Go on a kayaking tour of Fort Gorges with Portland Paddle, then head to Flatbread Portland for lunch on the waterfront deck, a location that offers a great view. The ingredients are all sourced locally and the pizzas are particularly delicious. They even have a public dock if you happen to go there with a boat.

Shop on Exchange Street

After lunch, discover the shops on Exchange Street, where you’ll find many independent boutiques of clothing and home goods, along with the works of local artists.

Dine at Evo Kitchen and Bar

Freshen up at the Press Hotel, then dine at Evo Kitchen and Bar, a restaurant that caters to gluten-free, vegan and vegetarian diets and serves a Mediterranean-style menu. The chef was a champion on the TV show Chopped and his staff trained at some of the top restaurants in the country.

Finish off the night with a cocktail at Bar of Chocolate.

Day 2: Chebeague Island

body of water during sunset

Eat the best potatoes

Have brunch at Union (the restaurant inside the Press Hotel), which is a bit of a celebrity hotspot. But mostly you’ll want to go for the out-of-this-world menu and whatever you order, do not leave without trying the breakfast potatoes.

Take the ferry

Then, catch a ferry at Casco Bay lines to Chebeague Island, for a fun, relaxed afternoon. Take a round of nine holes of golf at the clubhouse, then make your way to the Chebeague Island Inn, a beautiful and unique place where you can relax on the lawn in the Adirondack chairs. Sip a cocktail and just enjoy the quintessential atmosphere. Eat lunch there or come back another night for their family-style dinners.

The freshest lobster

Catch the ferry back to Portland for a night on the waterfront at the Portland Lobster Company. Fishermen drop off the lobster on the deck, which is then steamed and served with an ear of corn. Savor it accompanied with a local beer while enjoying the live music.

Day 3: Explore Portland, Maine

lighthouse on cliff during daytime

Start your morning with coffee

Have coffee and a light breakfast at the Speckled Axe on Commercial Street and order one of their delicious seasonal lattes alongside a breakfast sandwich or a parfait.

Take a cycling tour

Once caffeinated, meet up with Summer Feet Cycling for a lighthouse bike tour, which is great fun for the whole family. From there, bike to Fort Williams in Cape Elizabeth to view the iconic Portland Head light, then cruise back to South Portland to Spring Point and Bug Light Park Lighthouses, before returning to town. Don't worry, the cycling tour makes stops for treats along the way!

Lunch and a sail

For a late lunch, try the fresh seafood rolls at Mr. Tuna in the Portland Public Market in Monument square. It started as a food truck, but became so popular it now has a brick-and-mortar store.

From there take a nice walk to Fore Points Marina (New England's premier Mega Yacht Marina). Grab a picnic basket with a charcuterie board from Charcute Marie and a bottle of wine or Maine craft brew and go for a sunset sail with Sail Portland Maine.

Dance the night away

Back in town, pick your adventure of either continuing on with the yachting community at The Marina Bar or, if you’re up for a wild night of dancing in a funky and kind of random place, head over to Bubba’s Sulky Lounge. Break it down on the light-up dance floor, where you’ll probably see someone in a banana costume (or something equally strange).

Day 4: Beach time

body of water during daytime

Today will be more leisurely. Grab a swimsuit and your bottle of sunscreen and head to the beach. 

Take your pick of any of the following, which are all very close: Willard Beach, East End Beach or hop on a Ferry to Peaks Island for a beach picnic.

There are also farther beaches that will require a short drive. Higgins is great for surfers, while Old Orchard is fun if you want to play arcade games, hop on a ride and grab an ice cream. York beach has stunning sand, a quaint location and iconic Nubble Lighthouse.

Another option is the Tides Beach Club, the ultimate resort style beach. Rent umbrellas, chairs and if you are lucky, they will serve you food and drinks on the beach. If you can't sweet talk the wait staff, head over to the Inn to grab lunch and cocktails. Their happy hour is delightful, too!

Tacos and movie night

After freshening up at the hotel, and head out to Bayside Bowl for tacos and movie night on the rooftop bar. Or enjoy the live music if it’s on. From here, feel free to hop around or head back to the hotel for a night in.

Day 5: Take in the view (and one last bite)

lighthouse next to body of water during sunset

If you have a couple of hours before your flight home, grab a coffee and a donut made with Maine Potatoes at Holy Doughnut. Then walk over to Commercial Street to enjoy the last little bits of Portland. Sitting on a bench on the waterfront to breathe the fresh air and take it all in is so relaxing to do while the city is still quiet.

Need to Know

This itinerary is just a taste (pun intended) of what Portland has to offer. The destination is known for its outdoor activities, rugged coastline, and down east (as this area of the coast of Maine is called) hospitality. There are hiking trails within a short drive of the city and you can also go white-water rafting, plan a wellness retreat or even stay on a private island. There is so much to do on vacation land!

For more travel tips, check out this guide by Fora Advisor Amy Barraclough: Guide to a Girl's Getaway in Portland, Maine.

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