A Weekend In Portland Maine

If you’re looking for the perfect long weekend getaway with coastal charm, amazing food, and quintessential New England vibes, Portland, Maine, has your name written all over it. From iconic lighthouses to cozy coffee shops and fresh seafood, Portland offers the perfect mix of adventure and relaxation. Were from Orlando, so we took a one way trip through Breeze Airways straight to Portland Maine! Here’s a fun and friendly guide for a 3-day trip designed with YOU in mind! Make sure to check out my blog for more posts and follow me on instagram!

Day 1:

Welcome to Portland! Start your trip with a laid-back day soaking in the heart of this charming city.

Where to Stay:

• Canopy by Hilton Portland Waterfront: This is where we stayed! Great location and walking distance to downtown and all the shopping and restaurants. If you’re renting a car, they will valet it for you and it’s going to be more affordable than doing it yourself so I suggest just eat the cost. There’s a rooftop bar called “Luna” that is so pretty at night and the downstairs “Cafe + Bar” Salt Yard is perfect for coffee in the morning without going too far!
• The Press Hotel: Located in the historic Portland Press Herald building, this boutique hotel is both stylish and cozy, with art-inspired decor and an unbeatable location.
• Inn by the Sea: A luxury beachfront option just minutes outside the city, perfect if you love coastal vibes.

What to Do:

• Explore Old Port: Stroll through cobblestone streets lined with boutiques, art galleries, and waterfront views.
• Visit Commercial Street: This bustling area offers great photo ops and a chance to peek at the working waterfront.

Where to Eat:

• Cheese Louise: Known for their gourmet grilled cheese creations, they pair perfectly gooey sandwiches with flavorful twists, making each bite unforgettable. Whether you’re a fan of classic combinations or crave something a little more adventurous, this cozy eatery serves up comfort with a side of creativity. A must-visit for locals and travelers alike!
• Lenora: From freshly made guacamole to beautifully crafted tacos and flavorful mole dishes, each plate is a celebration of tradition with a modern twist. The warm ambiance, friendly service, and bold, colorful flavors make it the perfect spot for a memorable evening. The street corn is delicious along with the Tijuana Caesar!
• The Holy Donut: For dessert or honestly anytime, grab a Maine potato donut! Flavors like sea salt chocolate will win your heart. I heard so many folks recommend so we have to try, and it did not disappoint!

Coffee Stop:

• Tandem Coffee Roasters: A must-visit for coffee lovers, housed in a renovated gas station with the dreamiest lattes and pastries.
• Bard Coffee: Known for their dedication to quality and sustainability, they source and roast their beans with care. With its cozy atmosphere and prime downtown location, Bard Coffee is a favorite for locals and visitors looking to savor a moment of caffeine bliss. I ordered a cappuccino to go, yum!

Day 2:

Ready to dive into Portland’s coastal beauty? Today is all about iconic views and fresh sea air.

What to Do:

• Portland Head Light: You can’t visit Portland without seeing its most famous lighthouse! Located in Cape Elizabeth, this picture-perfect landmark offers stunning ocean views and a rich history. We went in November, so it was pretty chilly and windy so dress warm if youre going around Fall. The views were gorgeous, I couldn’t stop taking photos. Definitely a highlight spot!
• Fort Williams Park: While you’re at the Portland Head Light, explore the park’s walking trails and picnic spots.
• International Cryptozoology Museum: Got an hour to kill and a curiosity for the weird? Swing by the International Cryptozoology Museum in Portland, Maine, where Bigfoot is the VIP. From Sasquatch to sea monsters, this quirky museum is packed with oddities that’ll leave you scratching your head and chuckling at the same time. It’s the perfect way to embrace your inner skeptic – or full-blown believer – while ticking off a truly unique stop on your Maine adventure!

Breakfast Spot:

• Hot Suppa: Portland’s go-to breakfast haven where comfort food reigns supreme. The cheese grits were divine and an amazing plate of Eggs Benedict, get there earlier than later, the wait was about 25 min for us. It’s a small restaurant that’s packed with flavor.

Lunch Spot:

• Luke’s Lobster: A visit to Portland, Maine, isn’t complete without a stop at Luke’s Lobster for their iconic lobster roll. This lunchtime favorite is loaded with sweet, tender Maine lobster, served simply with a touch of mayo, lemon butter, and seasoning to let the fresh flavors shine. With waterfront views and a laid-back vibe, it’s the perfect spot to savor the taste of Maine while soaking in the coastal charm. We sat upstairs and I even had a seal sighting from the water! So cute!

Afternoon Adventure:

• Casco Bay Ferry Ride: Take a ferry ride to the nearby Peaks Island for a peaceful escape. Rent a bike and explore this quaint island, just a short trip from downtown.

Other spots to check out!

• The Juicery: If you take a stroll downtown, and are in the search for fresh juices, check them out!
• Oxbow Brewing Co: Brewery fan? There’s a a few to check out but we went to Oxbow Brewing. Their farmhouse ales and barrel-aged brews are top-notch. Swing by their Portland spot or Newcastle for a unique craft beer experience.
• Two Fat Cats: Hands down the best short bread cookie I’ve ever eaten!

Dinner Pick:

• Via Vecchia: Make your reservations in advance or you can take a chance by sitting at the bar as well. The have small plates, pasta, craft cocktails and more! Don’t miss their delectable appetizers or house-made desserts – it’s so delicious and the building is beautiful inside and out!

Day 3:

Make your last day in Portland a mix of creativity and leisurely fun.

Morning Coffee Stop:

• Speckled Ax: Try their wood-roasted coffee for a unique and delicious flavor.

What to Do:

• Portland Museum of Art: Dive into Maine’s vibrant art scene with works by Winslow Homer and more.
• Shopping in the Arts District: Browse through unique shops, from local jewelry makers to bookstores.
• Eastern Promenade: Take a leisurely walk with breathtaking views of Casco Bay—it’s the perfect spot to unwind before heading home.

Lunch Spot:

• Duckfat: Indulge in their famous Belgian fries (dipped in truffle ketchup, of course) and a decadent milkshake.

Wrap-Up:

• Before you leave, grab some local goodies at Standard Baking Co. Their pastries and bread are perfect souvenirs (if they make it home without being eaten!).

Tips for Your Portland Getaway

• Seasonal Charm: Visit in late spring, summer, or fall ( will be a tad chilly ) for the best weather and colorful scenery.
• Pack Layers: Maine’s coastal weather can be unpredictable, so bring a light jacket even in summer.
• Be Curious: Portland is full of hidden gems. Don’t be afraid to wander and discover your own favorite spots!
• Parking: If you rent a car, don’t be surprised to end up paying for parking. We found parking meters everywhere and most ranged between 12-25 bucks for 2 hours, it all depends.

Heading Back Home

You can see a lot in a 3 day trip in Portland, Maine! It was more of a foodie spot than I thought which was a good surprise for me. The views of Portland headlight are seriously my favorite too, that alone was straight from a storybook! I hope you enjoy your trip! Safe travels!