Ultimate 3-Day Portland, Maine Travel Guide

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September 12, 2024 • 6 min read

Scenic view of Portland, Maine
Be inspired to spend a weekend in Portland, Maine, with these top tips from a recent visitor.

The following is a review of a weekend spent in Portland, Maine, capturing highlights and recommendations to prepare for your visit.

I’ve always envisioned what visiting Portland, Maine would be like, characterized by buttery lobster, charming local shops, and scenic sailing. Despite never having been to Maine before, I planned a long weekend getaway, encouraged by my grandmother who had two key pieces of advice: indulge in local cuisine and visit the local gift shop for some unique souvenirs.

To assist you in crafting your own unforgettable experience, here are some highlights from my recent weekend in Portland.

The interior of The Longfellow Hotel
The Longfellow Hotel offers a cozy atmosphere with a focus on sustainability.

Where to Stay in Portland

The Longfellow Hotel, located in the West End, is a newly opened boutique hotel committed to sustainability. On our first morning, we enjoyed a delightful room service breakfast featuring an iced oat milk latte and a breakfast sandwich that exceeded expectations.

Moreover, the hotel’s bar offers a creative mocktail menu, perfect for those who prefer non-alcoholic options. My choices—a Rosarium and a Vacationland Refresher—were refreshing and well-crafted.

Don’t miss out on the excellent spa experience at the hotel; they offer a variety of massages and treatments designed to rejuvenate and relax. The Mindful Dreams massage left me feeling completely pampered.

A variety of dishes in Portland
Portland is renowned for its vibrant food scene, making it a must-visit for food enthusiasts.

Culinary Delights

Portland’s culinary reputation is well-deserved, offering a diverse array of dining experiences. Here are a few highlights:

  • Brickyard Hollow Brewing Company – Known for its gourmet pizza, the cheese pizza offered a deliciously simple yet satisfying taste.
  • Green Elephant – A vegetarian restaurant that serves fantastic deep-fried spring rolls and ginger noodles; a must-try for vegetarian food enthusiasts.
  • Benkay – A Japanese restaurant offering a delightful teriyaki tofu dish, bursting with flavors.
  • Holy Donut – Perfect for those with a sweet tooth; don’t miss the blueberry-glazed donut!
Tourists taking a photo on a boat
Capturing memorable moments during a scenic boat trip in Casco Bay.

A Scenic Cruise Experience

To conclude our trip, we embarked on a sunset cruise in Casco Bay. It’s advisable to book your tickets in advance, as many tourists were turned away due to capacity limits. The experience was breathtaking, showcasing beautiful views of the islands and tranquil waters.

A shop showcasing arts and crafts in Portland
Discover unique gifts and art in Portland’s historic Arts District.

Shopping in the Arts District

Maine’s historic Arts District is a vibrant shopping destination. Visit local shops such as Soleil for unique gifts and crafts, and Loquat where you can find locally made items and creative designs.

Packing Essentials

When preparing for your trip to Portland, consider packing layers and comfortable shoes. The city is walkable, and layering ensures you’re ready for any sudden weather changes.

Final Tips for Your Portland Adventure

  • Explore local eateries and don’t hesitate to try something new.
  • Take advantage of outdoor spaces and scenic views while walking around the city.
  • Remember to book activities in advance, especially during peak tourist seasons.

In conclusion, Portland, Maine is a treasure trove of culinary delights, picturesque views, and cultural exploration. With planning and an adventurous spirit, your weekend getaway can be as memorable as mine.


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