If you're dreaming of salty ocean air, postcard-worthy lighthouses, fresh seafood, and charming coastal streets, Portland, Maine deserves a spot on your travel list. I spent three days celebrating my 40th birthday exploring this quintessential New England city, and it quickly won me over with its perfect blend of adventure, history, and waterfront charm.
From pedaling along the coast on a lighthouse bike tour to watching the sun set over Casco Bay on a scenic harbor cruise, every day offered a new perspective of Maine's rugged beauty. In between, we wandered the cobblestone streets of the Old Port, browsed locally owned boutiques and bookstores, indulged in some of the freshest oysters and lobster I've ever had, and never passed up an opportunity to stop and admire the harbor views.
Whether you're planning a girls' getaway, a long weekend, or simply looking for the perfect coastal escape, here's how to spend three unforgettable days in Portland, Maine.
Day One:
Lighthouse Bikes offers a lesiure 5 mile bike tour of two historic sights: Bug Light and Spring Point Light. Along the way guides will tell insightful stories and history, stop for photos and have you ride along iconic picturesqu harbors.
Grab caffine at Matcha Mood. Their menu is a matcha girl's dream, featuring flavors like strawberry, purple ube, black sesame, coconut cloud, Biscoff, yuzu lemonade, and more. You can customize your drink with coffee jelly, order it iced, hot, or blended as a frappe, making it easy to find your perfect matcha mood. I went with the Purple Matcha, an iced matcha with ube and lavender and it was just as delicious as it was photogenic!
Wander around Maine’s first and only all-romance bookstore Grump & Sunshine. Say hi to the bookstore dog Jace and grab your next happily ever afrer read. I went during the World Cup games and got Relationship Goals by Brittany Kelley.
Enjoy a local brew at Austin Street Brewery. Open concept vibe with both indoor and outdoor seating. They are known for their corn dogs and you can do a happy meal on Wednesdays and get a corn dog and beer for a discounted price! I enjoyed a glasss of “After the Glitter Fades” Tart Blonde Ale with Mint & Lime and it was so refreshing!
And right behind the breweryyou will find an indoor mini golf, Mini Bar Golf. We went on a Wednesday because they have 75 cent wings wednesday and $10 all you can play. It was so much fun here, 18 custom-designed mini golf holes, 20 taps pouring local favorites, 32 screens highlighting your favorite sports, and a flavor-filled menu of apps and bar food that will make your mouth water! Some of the holes have games to prompt competition and they have digital score keeping!
Day two
Start the day with famous gourmet potato donuts at Holy Donut! Started by a a visionary single mother, who her apartment kitchen into a donut laboratory fueled by a desire to offer a healthier donut that she felt comfortable sharing with her daughter. With so many fun flavors to try, I opted for the Lavendar donut!
Have shopping be your cardio on Commercial Street along the harbor. There are so many cute shops owned by local artisans. You can find clothing, jewlery, things for the home, souveiners and snacks along the way. Some of my favorites Old Port Cardworks, Casco Bay Artisans, and others along the way!
Lunch at Highroller is a must! Known for their lobster rolls and beer, the menu has also expanded to include oysters, red snappah red hot dogs, grilled cheese, whoppie pies and more! We opted for hot lobster rolls with butter, red hot dogs, chicken nuggets and a variety of fries.
Test your skills at the Arcadia barcade, there are an assortment of vintage video games, skeeball, claw machines, pinball and so much more in this two story barcade. There is also a full bar, with some fun cocktail options and food items like pizza, hot dogs, and sweets! You can win tickets to claim a prize at the end too!
The views of the harbor are spectacular but what better way to see everything than by water? We booked a 7pm Susnset Cruise of Casco Bay and it was breathtaking! They have a bar on board to bring drinks and we brought snacks. There is a roof observation deck with rows of chairs, there are tables and chairs in a covered area on the main deck and you can wander around the boat to take all the pictures!
If you take a cruise from the main pier, walking distance you can get the best Italian food at ViA VECCHiA. Located in an iconic brick and ivy covered building overlooking cobblestone streets, it has the perfect evening out vibe. All of their wine is imported but our server was so knowledgeable in helping each of of find something that went well with our meal and that we would love! The focaccia and aranchini is a nonnegotiable to start with, both were amazing! The chicken marsala and campanelle were table favorites but everything was fresh, flavorful and delicous!
Day three
Tandem Coffee in the West End, get there early there is always a line becuase the coffee and freshly baked goods are amazing. This place was so good, we went every single morning! They are known for their buscuits and for good reason! I had to have the loaded savory: Buttermilk biscuit with Fredrikson Farm goat cheese and house made tomato jam and it was 100/10! They also have cookies, scones, pie and quiche!
Relax on Portland’s only public beach, Eastern Promenade. The pebbly waterfront is popular for kayaking, launching boats, and enjoying sweeping views of Casco Bay, all just a 15-minute walk from downtown.
Shipyard Brewing & Tasting Room was a great stop for the group, lots of seating and a variety of drink options. Beers on tap, prosecco or vodka, CBD or THC drinks and sodas give a wide range so everyone can find something. I mixed their Blue Lobster Prosecco with the Blueberry Seltzer with 10mg of CBD for a relaxing refreshing drink.
I love to stumble upon art and when we found a street and alley filled with murals it became the backdrop of so many photos!
The Grill Room & Bar needs to be on the list if only for the best espresso martinis! This urban steakhouse has a great vibe and the bar was so much fun! The staff was fantastic, bartenders made the best drinks, shoutout to Karl! Another favorite was the Maine Blueberry Gin & Tonic but they also have a mocktail list and variety of beers. They are known for their beef tartare and steak but also have oysters, pizza, and lobster mashed potatoes that were great!
