10 Fun Things to Do in Portland, Maine

Sunset falling behind the sky and the skyline of Portland, Maine

Are you looking up New England towns for a quick weekend getaway and asking yourself, “Is Portland, Maine worth visiting?” because the answer is absolutely yes. The east coast’s Portland is honestly so cute and definitely worth a stop on your New England trip. I’ve been three separate times and each time I’m enchanted by how adorable it is and what new things I can do. Whether you’re looking to spend a few days in one of the most charming little cities in New England or need an itinerary for Portland, Maine, I’ve got you covered. Let’s dive into some of the top things to do in Portland, Maine!

The Short Version

The short version of things to add to your Portland, Maine itinerary is as follows:

The Long Version of the Top Things to Do in Portland, Maine

While there are so many amazing things to do in Portland, these are some of the activities that I’ve really enjoyed on my visits.

As always, if you buy anything through one of my links, I may make some commission, from your purchase. I truly appreciate any support in that area, but also want to make sure you know that I wouldn’t recommend something I didn’t believe in, so these all have the Amanda Wanders stamp of approval.


Where to Stay in Portland, Maine

Whether you’re needing somewhere to stay for a Portland, Maine weekend getaway or a longer stay, there are lots of hotels to choose from. I’ve stayed at both the Embassy Suites and the Fireside Inn and Suites. Neither of them are necessarily fancy – the Embassy Suites more so than the Fireside – but they get the job done. I’m not the type to stay at my hotel often during a trip anyway, so these were both perfectly fine though I wouldn’t call them necessarily walkable to downtown Portland.

If I were looking at staying somewhere based on it being adorable and closer to the walkable areas of Portland, I would almost certainly stay at one of the following:

Here are some other Portland, Maine hotels to check out for your getaway:


Go on a Sunset Sail

I was SO excited to go on a sunset sail in Portland. I’d never been on a sailboat and this was such a highlight of my multiple trips to Maine. I highly recommend going sailing – whether you can make it work for sunset or not – because it’s an absolute blast. This is for sure one of my top things to do in Portland, Maine and I would do it again in a heartbeat.

I originally booked my sail with Sail Portland Maine, but there are a few companies who offer similar experience, so shop around and see if you can find a time slot and price that works for you (ideally sunset)!

Go on a Food Tour

Some of us travel for incredible natural beauty and some of us travel for delicious food. And some of us travel for both, and lucky for you Portland is a perfect destination for both. There are lots of food tours offered in this adorable little town and you should definitely add at least one to your Portland, Maine itinerary!

Check out the Many Breweries

Portland, Maine has a great craft beer scene and there are tons of places to grab a good beer at. Here are some I’d recommend:


Take the Ferry to a Neighboring Island

A pretty unique thing to do in Portland, Maine is to actually hop on a ferry to one of the islands nearby. I’ve got a blog all about the top things to do on Peaks Island, which is an awesome day adventure from mainland Portland. But there are a few islands you can choose from – as well as not stopping on any island at all and simply riding the mail ferry and getting a tour of the bay. This was a surprising hit on my Portland, Maine itinerary.

Visit the Famous Lighthouses of Portland, Maine

No “best things to do in Portland, Maine” list or itinerary is complete without visiting at least one of the very famous lighthouses. The Portland Head Light is one of the most photographed lighthouses in America (and I think maybe the world), but it’s not the only one! If you’re a fan of lighthouses and maritime things, check out the Bug Light, Ram Island Ledge Light, Two Lights State Park, and Spring Point Ledge Lighthouse.

Explore the Old Port and Commercial Street

Honestly just walking around Portland, down on Commercial Street and over by the Old Port is so much fun. It’s such an adorable city and there are so many cool shops, restaurants, bars, and more that you can absolutely spend a day of your Portland itinerary wandering around.

Eat Your Weight in Lobster Rolls & Other Local Gems

One of the absolute must do activities when visiting Portland, Maine is to eat some lobster rolls. Over my three trips, I’ve decided on my favorite lobster rolls and compiled them into this list of the best lobster rolls in Portland.

Soak in the Sights at the Eastern Promenade

The promenade is a beautiful spot in Portland to sit down and enjoy some gorgeous weather and views. It’s got an amazing view of the harbor and tons of space to go on a walk along the trail, have a picnic, and relax. Bonus? If you’re up for sunrise one day, this is going to be an incredible spot to watch the sun peak up over the United States.

Visit the Portland Observatory

The Portland Observatory is one of many historical relics still standing in this adorable city. It is the only remaining maritime signal station left in the United States, so if you’re into historical landmarks like that, definitely book a guided tour where you can tour the tire and even go up to the top for incredible views of the city.

Go Whale Watching

I didn’t actually get to do this because the weather didn’t cooperate when it was booked but I’m a massive fan of going whale watching any and every place I can, so I highly recommend this if you’re in Portland during whale watching season. I had a friend go a couple weeks after I was supposed to and had the absolute best time. Odyssey Whale Watch is the only company out of Portland, Maine offering whale watching tours, so you’ll definitely need to book with them.


So there you go, 10 fun and unique things to do in Portland, Maine. As always if you have any questions, please don’t hesitate to reach out. To see more of my on-the-ground experiences doing lots of these things I’ve recommended, check out my Instagram highlight of Portland, Maine.

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