Embark on a sweet escape to Portland, Maine, filled with wonderfully cozy hotels and a delightful array of cultural festivals and events. This list is all about creating beautiful memories together, whether you're relaxing in charming accommodations ...
This hotel is super chic and oozes character. I love how it used to be a newspaper building, which gives it a unique, vintage vibe. The rooms are comfy, the decor is artsy, and the service is top-notch. Plus, it's right in downtown Portland, so every...
The Press Hotel - 4-Star Luxury Hotel in Portland, ME - Marriott
This place has such a cozy, romantic feel with a touch of luxury. The rooms are beautifully decorated, and I really enjoyed their courtyard garden – it's a perfect spot for morning coffee. It's also close to the waterfront, so you can easily enjoy th...
Portland Harbor Hotel
Staying here felt like being in a gorgeous, secluded paradise. The rooms are spacious with stunning ocean views, and we loved having a fireplace in our suite for those cozy nights. The spa is fantastic, and the beach is practically at your doorstep, ...
Inn by the Sea
This historic hotel has so much charm and the perfect balance of old-world elegance and modern comforts. The staff is incredibly attentive, and the spa is a real treat. The location is great too – right in the Old Port district, surrounded by cute sh...
Portland Regency Hotel & Spa
If you're into wine, this week-long festival is an absolute must. There are tastings, dinners, and cool events hosted by local winemakers. It's such a fun way to explore different wines and enjoy the vibrant atmosphere of Portland.
Portland Wine Week
This festival is a blast! It's mostly held in Rockland, but a short drive from Portland. Expect delicious lobster dishes, a fun parade, and live music. It's perfect for a day trip filled with local culture and amazing food.
Maine Lobster Festival
This annual festival is great for experiencing the local culture. There are street vendors, live music, and lots of local food and crafts. It's a fun and lively way to spend the day together and maybe pick up some unique souvenirs.
Old Port Festival (Official Event Page) - Facebook
On the first Friday of every month, Portland's art scene comes alive. Galleries, museums, and studios open their doors, and there’s art everywhere. It's incredibly romantic to wander the streets and enjoy the creativity hand in hand.
First Friday Art Walk - Creative Portland
Catching a minor league baseball game at Hadlock Field is super fun and casual. It's a great way to relax in the summer and enjoy some classic Americana vibes. And don’t forget to share some popcorn or hot dogs!
Hadlock Field
This food and drink festival is a haven for foodies. We loved the tastings from local chefs, the craft brews, and the overall festive atmosphere. It's an excellent way to indulge in some amazing culinary creations together.
Harvest On The Harbor
Exploring this museum was such a lovely way to spend an afternoon. The art collection is impressive and diverse, featuring both local and international artists. It's a great spot for a quiet, romantic stroll while immersing yourselves in beautiful ar...
Portland Museum of Art
This historical mansion is like stepping back in time. We were fascinated by the Victorian architecture and beautifully preserved interiors. It's a wonderfully romantic and unique place to explore together for an hour or two.
Victoria Mansion
For a relaxing day outdoors, this park is perfect. It's lush and green, with pretty walking trails and a lovely pond. We brought a picnic and just enjoyed the scenery. Great for some downtime and connecting with nature.
Deering Oaks Park
Enjoying a performance by the symphony orchestra was such a sophisticated and romantic experience. The music is beautiful and moving, and the concert hall itself is elegant. It’s perfect for a date night that feels truly special.