The Best of Portland, Maine in 24 Hours

Get the Best of Portland with these tips on how to spend 24 hours in Portland Maine. Woman in front of Portland Head Lighthouse

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This year I had the incredible good fortune to visit Portland, Maine during a Women in Travel Summit. While I did spend more than 24 hours in the city, technically, I was busy attending the conference. However, I put together what I think is the Best of Portland, Maine with a complete 24-hour itinerary.

Visit Portland did provide some tours to attendees of the Women in Travel Summit. However, all opinions are my own.

About Portland, Maine

At the southern edge of Maine, Portland is the perfect introduction to all the state has to offer. Okay, true, Portland is about an hour away from the border of Maine and New Hampshire, but it is the largest city by population in the state of Maine. That being said, it’s still a small town by many standards at roughly 67,000 residents.

Portland is not just a part of the greater outdoors nature of Maine. It’s artistic, multi-cultural, and exquisitely culinarily diverse. With such a mix of nature and foodie finds, it would be easy to spend more than 24 hours in Portland, but here’s how to get the best taste.

Holy Donut

Start your day at Holy Donut on Exchange Street. This popular donut shop creates a variety of flavors the way only Mainers could, with potato donuts. If you’ve never had a potato donut, it’s not what you think. Surprisingly lighter than a flour donut, Holy Donut uses fresh Maine potatoes that keep the donuts moist. I should know, I took home a box of six to the hotel and I’d like to say they lasted a long time. In truth, I think I ate 3 in one day!

Flavors change daily and the shop closes when the last donut is sold, so plan to go early!

Get a Lucky Catch

One of the best and most unique things to do in Portland Maine is Lucky Catch Cruises. Just a short walk to the Long Wharf pier from Holy Donut, Lucky Catch Cruises offers lobstering excursions daily from May through October.

Take the 10:30 Portland Headlight cruise and you’ll get sea view of Portland’s iconic Headlight lighthouse (one of the most photographed in the world.)

The highlight, however, is catching lobsters. Maine is very strict in their lobstering laws, and you’ll learn the right length and what you need to do to become a lobsterman.

woman with lobster as one of the many things to do in Portland, Maine

After your cruise, take your lobster right next door to the Portland Lobster Company to get it steamed and served for lunch. Or order from their full menu. This dock-side bar will not disappoint.

Greater Portland Landmarks

By now you may need to walk off lunch a bit and a great way to do that is a self-guided or hosted walking tour through Greater Portland Landmarks.

best of Portland, Maine buildings
Rumor has it that’s a cannonball lodged in the building

The city if full of history, as it was once one of the top ports in the Northeast. And since the city is easily walkable, you can see a lot in just a short amount of time.

Check out the reviews of Victoria Mansion by my friend Christine for exquisite details.

Try to squeeze in a visit to the Custom’s House before departing on your next adventure. Or save it for when you return.

Maine Brew Bus

Well after lunch is the perfect time to hop on board the Maine Brew Bus. Easily one of my favorite tours in Portland, the Maine Brew Bus starts as early as 10 am on Saturdays, with “last call” at around 5 pm most nights of the week.

The Maine Brew Bus is one of the Best of Portland, Maine

While most of the tours are focused on beer, Maine is one of the largest craft beer states in the country, you can also enjoy wine and spirits on some of the tours. Try the Fermented Friday with a visit to one brewery, one winery, and one distillery.

Additionally, your guide provides sightseeing and history in between stops.

Maine Foodie Tours

If beer and wine aren’t your things, Maine Foodie Tours offers a variety of Portland walking culinary tours. Choose from street food, lobster crawls, and more.

Portland Head Lighthouse

After a fun foodie or brew tour, a trip to Portland Head Lighthouse (via Uber or Lyft if you’ve been drinking) may time you right at sunset. Even if it’s still a little early, late afternoon is a lovely time to walk the nearby seaside cliff walking paths to work off some everything you’ve had to eat!

The Portland Head Lighthouse is iconic and the best of Portland, Maine

The lighthouse is both iconic in looks as well as historical significance, dating it back to 1791 as a commission from George Washington. It is Maine’s oldest lighthouse and sits in a 90-acre park. Plan to spend an hour here walking the trails, photographing the lighthouse, and exploring the museum.

If you have more time, I highly recommend doing a Lighthouse Tour. Check out Tyra’s self-guided lighthouse itinerary here.

Alternatively, you could visit several lighthouses in a guided tour such as this one.

Art Walk

If you happen to be in Portland on the first Friday of the month, take part in the First Friday Art Walk where galleries and museums open for free viewings.

Checking out some art installations

We had a great time meandering the streets for an hour or so before we headed out to the Improv show (see below). For even more info, check out Portland’s Lively First Friday Art Walk here.

If it’s Friday, but not the first Friday, the Portland Museum of Art is free from 4-8 and worth a visit.

As you stroll through the. streets, take note of the variety of dining available.


Speaking of dinner, Portland is an epicurean haven of epic proportions. I don’t know how it’s possible to narrow it down to one place in 24-hours, so I’ll leave that to my fellow travelers for their recommendations.


After dinner, head out for some quality entertainment. Portland boasts a wide variety of theater, the Portland Symphony Orchestra, the Portland Ballet, and comedy shows.

The Fresnel Theater, located in the basement of 1 Monument Square Building, provides side-splitting improv-style comedy shows. Whether it’s a ComedySportz style pitting two teams of improv comedians against each other or even more adult entertainment with Past Your Bedtime, this is a low cost yet highly enjoyable venue.

Fresnel Theater Improv Troupe with the Women in Travel Summit as the Best of Portland, Maine

After Hours Cocktails

Your evening can continue with after-hours cocktails at a variety of places.

Dimillo’s on the Water is a docked “boat” with magnificent views of the Portland Harbor. Get a second bite to eat or just grab a table for drinks and dessert.

If you’re lucky and can snag an event at Grace, do it. This stunning church turned event venue is breathtaking.

Portland was once an ardent protester against prohibition. Thus, a speakeasy is a perfect way to cap the evening with drinks… if you can find it. Search for Lincoln’s where everything will cost you just a Lincoln (a $5 bill.) It’s a hidden gem.

Portland Maine Hotels

Finally, you need a place to rest your head for the evening. Portland has a great mix of luxury, budget and a few unique places in between.

I stayed at the Inn at St. John my first night and found it utterly charming. It’s the city’s oldest continuously operated Victorian Inn.

The Press Hotel is another unique find. Themed as if you just stepped into a newspaper office complete with typewriters (on the wall) and printing press accents throughout. As a writer, this place is irresistible. Bonus, it’s also part of Marriott’s Autograph collection so you can earn and use rewards.

The Black Elephant Hostel is a gorgeous budget option popular with many of the travel writers. It is a communal hostel but offers female-only bunks, and private rooms.

Even More to do in Portland

Do you have more time to spend in Portland? Check out these recommendations from fellow travelers.

This book has all the things you need to do in Portland. Plus, it was written by our personal guide throughout the week and Visit Portland’s representative. You can’t get better than this!

Work your way up the coast and check out 24 hours in Freeport, Maine too.

The best of Portland, Maine

1 thought on “The Best of Portland, Maine in 24 Hours”

  1. Awesome post. I’d go make in a minute!! Wits19 was a great conference too. Thanks for including my blog post in your article. Kim – Forever Green Mom

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