Travel Guide: 48 Hours in Portland, Maine

Summer on Maine’s coast is nothing short of iconic. In Portland, the city truly comes alive during summer, staying true to its namesake “Vacationland.” Now that COVID-19 restrictions have begun to lift in the state, there’s no better way to spend a weekend. Below, we’ve put together a 48-hour travel guide to your next weekend in Portland, including everything from mouthwatering lobster rolls to an epic Maine sail. Read on!

Friday

Driving up on Friday afternoon? Try to make it early enough to catch the sunset in the historic, Victorian mansion-filled West End of Portland. There are several local restaurants in this trendy neighborhood that are offering take out options: Chaval offers Spanish-style small plates, while Little Giant also cooks up European cuisine alongside mouthwatering cocktails. Grab dinner to-go and take your picnic to the West End Promenade to sit back, relax and enjoy the sunset.

weekend in portland maineSaturday

Wake up early and grab a strong coffee and breakfast to go. Some of our favorites include Speckled Ax, Bard, or the infamous Tandem Coffee. Once you grab fuel, make a morning out of exploring the rest of the city, specifically downtown Old Port and the East End.

The Old Port, which is the heart of Portland, is the perfect mix of original cobblestone streets and chic boutiques, seaside restaurants and art galleries. Though there are still some restrictions due to the pandemic, it’s ideal for a slow-paced morning of sightseeing. The East End boasts a rolling green park with panoramic views of the Casco Bay and is ideal for laying out and relaxing. We’d recommend grabbing a snack from one of the many food trucks that park along the adjacent road to enjoy while you lounge.

After you’ve rested up, grab a late lunch/early dinner at a restaurant with a patio. Luckily, Portland offers basically everything you could be craving, so you’ve got options! Try Highroller Lobster Co. for endless variations of lobster, Taco Escobarr for incredible margaritas and nachos, or DiMillo’s for a slightly more upscale, waterfront meal.

The best way to end your day? Enjoying a breathtaking sunset sail in the Casco Bay with Sail Portland Maine. On Saturdays, we offer two hour sunset sails featuring a delicious rosé to indulge in as you take in lighthouses, islands, forts, and seals frolicking in the harbor. Our professionally-captained charters offer the intimate, crowd-free experience of a Maine sail – there are never more than 6 passengers aboard our boat, and you can even book private charter sails. Reserve your trip today!

Sunday

Don’t rush home on Sunday morning! Instead, sleep in and grab a leisurely breakfast. Depending how hungry you are, there is no limit to dining options. If you’re looking for something light, try the loaded smoothie bowls from Blake Orchard – every option is delicious and you can even customize your own. For a heartier brunch, check out Hot Suppa, a tiny southern-style hot spot, or the Front Room for a classic spread.

On your way out of town, make sure you stop in Cape Elizabeth to see the iconic Portland Lighthouse and walk through the crumbling bunkers of the stunning Fort Williams. If you’re still hungry (hey, it’s a possibility!) grab a lobster roll or two from the Bite Into Maine food truck parked at Fort Williams for the ride home.

Keep in mind, this is just a small sampling of the incredible vacation options our beautiful state has to offer. Enjoy your summer with a fun-filled weekend in Maine!

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