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5 Must-See Spots on Your Portland, Maine Bucketlist

Updated: Jan 12, 2022

Have you ever underappreciated a city the first time you visited but gained appreciation over time? Portland, Maine, was that for me. The first time I visited Portland, Maine, was eight years ago. It was for a short period of time (a total of 3-4 days hopping to various Maine cities), so I did not get to know the city. This time, I returned for a 5-day trip and dug in deep, the Franny way. If you have followed me for long enough, you know what that means!


🇺🇸 Portland is the closest U.S. transatlantic port to Europe and the 20th-largest fishing port in the nation.

🇺🇸Portland is the birthplace of poet Henry Wadsworth Longfellow, author Stephen King, actor Judd Nelson, and five-time Olympic medalist Ian Crocker.

🇺🇸 Maine gained independence from Massachusetts and Portland became Maine’s capital in 1820, retaining that position until 1831

🇺🇸 At nearly 67,000 residents, Portland is Maine’s largest city! Greater Portland comprises 1/4 of the state's 1.3 million population.


🤩 Voted top for Coziest City

🤩 It’s Super Walkable

🤩 It’s Got Small Town Charm With Big City Foodie Culture

🤩 An Island Getaway Is Just A Short Ferry Away

🤩 Has 17 microbreweries—the most per capita of any city in the nation,

🤩 Ranks 8th for best places to live in the US

If you want to visit Portland, Maine, for the first time (or revisit more deeply), have these spots at the very top of your itinerary!

In this blog post, you will get info about:

  • What is Portland Maine best known for?

  • Is Portland Maine worth visiting?

  • How do I spend a day in Portland Maine?

  • What to do in Portland, ME?

  • What is Portland Maine Bucket List: Best Things To Do?

Table of Contents:

1. Sip & Sail

This is a unique experience I wish other places by water had — what’s better than sampling five different wines with a personalized charcuterie plate as you on a sailboat? The best part:

🍷 Woman-owned business using a female sail captain

🍷 Taste 5 wines in a particular theme ranging from Pacific Northwest to The Loire Valley to South Africa

🍷 Delectable mini charcuterie plate per person

🍷 Unique views of Maine,, including a few lighthouses

If you want to know how to book this luxurious, relaxing experience, check out my itinerary HERE.

2. Take an Observatory Tour

Just the views alone are worth it, but the history is more fascinating! No…it is not a lighthouse! This is Portland Observatory. They have a very informative, unique tour that gives a lot of historical context to Portland. Although it is seven flights of stairs, you stop at each level to learn some history and look at displays.

Some things to keep in mind when visiting are:

  • Visit August - October towards the end of the week: They are only open Thursday - Monday until October. They have walking tours during this time, which I missed.

  • Advanced time-entry tickets are required: Time slots sell out, so I would buy as soon as you know you are going.

  • A limited number of visitors: Up to 8 visitors are allowed at a time, and you have 45 minutes to check out the exhibits, explore, and marvel at the view from the top!

  • You cannot explore alone: Aside from the first floor, you must be escorted by a docent.

3. Try a Holy Donut

This isn’t just any donut shop. This is a potato donut that is actually delish! It is worth a try if you are an adventurous eater. Instead of baking traditional yeast and cake donuts, the shop makes donuts from potatoes…and it’s delish 😋 Along with flour and buttermilk, this shop includes Maine mashed potatoes. WHAAAAT 😯! This isn’t so far-fetched, considering that potatoes have been a part of the state’s history & economy. Irish farmers brought potatoes to Maine in the 18th century. In the mid 20th century, Maine was producing more potatoes than any other state in the country.

INSIDER TIP: Go early! They are only open from 6:30-1:30 pm or until they run out. We got there around 12 pm, and they were nearly sold out 😬

4. Explore Fort Williams Park

There is soooo much to do here. You can easily spend an entire day or even a couple of days here. These are my top recommendations:

⭐️ Stroll along with one of the many walking paths

⭐️ Take photos from different angles of the lighthouse

⭐️ Lick some tasty Gorgeous Gelato

⭐️ Grab a lobster roll from a food truck

⭐️ Explore Fort Williams Park

⭐️ Visit the lighthouse museum (limited hours)

⭐️ Attend a summer concert (if you can)

5. Portland Head Light

I mean, did you really come to Portland if you did not take a photo of the most photographed lighthouse in the USA!?! ‘Nuff said.

BONUS: Visit Peaks Island

Why not Island hop while in Portland? Peaks Island is the largest island to hop and spend a day. Such chill vibes!

Did you know Maine got islands!?! During my time in Maine, I took a day trip to Peaks Island, which was one of my fave parts of the trip! Less than 20 minutes away from Portland, it is easily accessible by ferry. It ain’t no Caribbean Island, especially with these cool temps, but it was a cute, small-town experience with only 1,000 year-round residents and 2,000 summer residents; yet, it is the most populous in Casco Bay, Maine. There is so much to do from taking a golf cart tour, visiting art galleries, eating seafood with a fantastic view, and licking some delish ice cream. Want to know what spots I went to? Check out my itinerary HERE.

INSIDER TIP: While there, check out the Umbrella Cover Museum. This is such a unique museum concept, and the owner is a sweetheart and very passionate about her curations! For more information, read my local business spotlight!

7. Get Your Portland, Maine Itinerary

Looking to go to Portland, Maine? Check out my 16 page itinerary that contains:

  • Lodging

  • Transportation: to get to location + while there

  • Links and contacts to all excursions & guides

  • Main attractions + hidden gems

  • Distance one location to next, organized to maximize time

  • Black-owned and/or local spots

  • Travel planner organizer for you to take your own notes

Which Portland, ME bucket list item are you most interested in doing? What has been your experience visiting Portland? Comment below!



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