6 Must-Have Experiences When Visiting Portland, Maine

Our quick, long-weekend trip to Maine was originally planned with the intent of checking off our last Northeastern state. But our one-and-a-half days spent exploring Portland ended up providing some of the best experiences, memories, and some of the most delicious eats.

       1. Take the Sunset Kayak Tour with Portland Paddle

Did you really visit Portland if you didn’t take part in the array of water activities available in the Casco Bay? After a quick overview on general kayak skills and safety instructions, we were in the water and ready for an hour and a half of adventure. Our guide was attentive, friendly, and knowledgable, providing us with information on the surrounding Casco Bay islands and pointing out a couple of Bald Eagles as they soared above us. Aside from the beautiful sunset, which ended up coming through as vivid as ever despite the clouds, my favorite part by far had to be when we carefully kayaked passed a small island covered in gulls and surrounded by seals. While we were instructed to not purposely paddle too closely to any wildlife, a few of the younger, more curious seals couldn’t help but swim up to a few kayakers in our group.

 I cannot recommend this tour enough, as I’m a sucker for sunsets and wildlife encounters, but Portland Paddle offers an array of other tours, including a Moonlight Kayak Tour and Lighthouse & Fort Full-Day Tour that I’m sure are equally as amazing!


2. Grab some donuts from the Holy Donut.

At this point, trying out popular foods fads has crossed over from an occasional overpriced hobby into a dedicated passion, so naturally I couldn’t visit Portland without  visiting their most publicized donut spot. But this donut shop is far from ordinary; selling donuts made from all-natural ingredients, including Maine potatoes. Yes, potatoes. Coming from someone who is typically not a fan of donuts whatsoever, I’m thankful I live six hours away because I would be here on a regular basis.

Of course, living so far from this gem meant I had to get in my share of flavors and so I ordered three different flavors even though one could easily feed two people. While the Blueberry Lemonade was the clear winner for me, the Coffee Cake Donut and Chocolate Sea Salt were nothing short of excellent. And if you’re worried about trying something out of your comfort zone, I did steal a bite of a friend’s maple bacon donut, which was out of this world!


3. Go sailing with Portland Schooner.

There is no better way to make the most of a hot day in Maine than by enjoying the breeze from an old-school Schooner as it sails down the Casco Bay. Portland Schooner is BYO, meaning you can bring your own lunch, beer, wine, etc. But be careful to hold onto your things when tilting from side to side; leaping to grab my backpack which was filled with all my camera gear, as it slowly slid towards the ledge was way more stress than I needed. Between the views, perfect weather, and “Come Sail Away” by the Styx playing in the background, this made for two of the most relaxing hours of our whole stay in Maine


4. Have a meal at the Lobster Shack at Two Lights.

Picture this. You’re sat along the rocky shore of Cape Elizabeth, with views of the waves as they break and Portland Head Light, the world’s most photographed lighthouse. Oh, and you’re eating the most affordable, yet fresh tasting seafood you’ve ever had. On first bite, I could already tell that my haddock had most likely been caught that same day and while I have had my share of outstanding seafood, this was beyond all expectations. Each “plate” at Lobster Shack is served with french fries, a biscuit, and a pickle-topped coleslaw. Easy to say I had a difficult time finishing, but of course when in Maine there is always room for blueberry pie. The blueberry mini pie at Lobster Shack is adorable and topped with a brown sugar, cinnamon crumble which pairs perfectly with the fresh blueberries. Forget Maine, this might be one of the best seafood spots I have ever eaten at.


5. Take in the view from the Portland Observatory.

Portland may not be the first city you think of in regards to scenic observation decks, but the Portland Observatory, which is definitely not a lighthouse, is a landmark worth visiting. For the last 210 years, the Portland Observatory has provided birds-eye views of Casco Bay and Portland Harbor, as well as a relaxing breeze during hot summer days.


6. Have breakfast at Three Sisters.

Three Sisters is actually in Biddeford, about 20 minutes outside of Portland, but if there was ever a breakfast spot worth going out of your way for, this is it. We learned rather quickly that Portland doesn’t have a substantial amount of breakfast spots, and after arriving at the uber-popular American Bayside Cafe only to be told there was a 50 minute wait, we decided to head to the first high-rated breakfast spot that we could find on Apple Maps. Besides being on the lower end price-wise, the dishes at Three Sisters were actually so good that we ended up going again the following day.

I wish I could’ve snapped a photo of my delicious Monte Cristo, which I ordered both days, but I ended up devouring the entire meal in about five minutes. If ham and Swiss sandwiched between two pieces of French toast, served with a raspberry jam and hash browns sounds as mouth watering to you as it did to me, this dish might be right up your alley.

Explore Maine, along with Massachusetts and New Hampshire on this New England Seacoast Tri-State Tour

Planning your own trip to Portland? Pin this on Pinterest for future reference!

6 Must-Have Experiences in Portland, Maine | A Great Big Hunk of World


19 thoughts on “6 Must-Have Experiences When Visiting Portland, Maine

  1. Any trip filled with wildlife, boat trips and food is good in my book 🙂 sounds like you had a great time in Maine! I’d love to visit one day! Thanks for sharing these experiences 🙂

    Liked by 1 person

  2. I’ve always wanted to try my hand at sailing! Portland seems like a great place to do so. Also those donuts look incredibly delicious, my mouth is watering at the sight of them!!

    Liked by 1 person

    • Have a great time! The Lobster Shack is definitely a great place to stop when visiting the Cape Elizabeth area. Bit crowded, but outstanding food.


  3. I’d love to do a road trip through New England one day – I’m a huge Stephen King fan, so Maine has always been on my bucket list. Portland sounds like a relaxing stop along the way – love the sea views 😀

    Liked by 1 person

    • That seems like it’d be a beautiful road trip! I’d love to eventually do a road trip though Maine up into Canada. I have only read a couple of Stephen King books but his imagery alway leaves me with a sense of wanderlust.


  4. Wow this was my first time reading about Portland. As a European I’ve never thought of visiting but after your post with so many different sea activities and lovely restaurants I will definately make a stop when I am in the area 🙂


  5. Oh gosh, you had me at sunset paddles and donuts! Within the next few years (read: when I save up enough money!!) I want to visit the States and hit up a whole bunch of cities, and I have definitely just added Portland to my ever-growing list!


  6. It’s been far too long since I went to Maine, and reading this, I can see I need to get back there soon. I love the idea of your schooner trip, although I’ll take note of the need to keep everything pinned down. And the lobster shack sounds just our sort of food.


  7. You had me at donuts and sunset kayak tour. It doesn’t get any better than that. The Portland Schooner looks like an unbelievable experience.


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