4 Day Trip to Portland, ME

Advisor - Alanna Zappariello
Curated By

Alanna Zappariello

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  • Portland, Maine

  • Couples Travel

  • Active Travel

  • Maine

  • Outdoor

  • Sightseeing

  • Countryside

blue sky over lighthouse
Curator’s statement

Just a short drive from Boston, Portland (Maine) has tons to offer from its various neighborhoods. This little town located right on the water will keep you busy all weekend long.

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Insider knowledge

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Where to stay

The Press Hotel, Autograph Collection

In the heart of Portland, Maine, this historic hotel features a fun newspaper-theme with rooms and suites styled as writer's offices.

Fora Perks
  • $100 hotel / resort credit.

  • Welcome amenity.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Advisor - Alanna Zappariello

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Day 1: Drive in from Boston

An aesthetic sight from top

If you are lucky enough to score a flight directly into Portland, then disregard this first part. From Boston, MA - rent a car and drive a short distance (1.5-2hr based on traffic) to Portland. Stop at Highroller Lobster Co before checking into the Press Hotel. The Holy Donut is also a great stop for a quick snack if you're not too hungry. The L.L. Bean Flagship store is 20 minutes away and definitely something not to miss. Make sure you get a picture with the big Bean Boot out front. For dinner, I recommend eating at The Maine Beer Company on your way back to the hotel. This brewery's motto is "Do the Right Thing" and all tips go directly to charity!

Day 2: Peak Island

Bunch bowl

Start your day getting brunch at the hotel's restaurant, UNION. Walk to the ferry port and buy a cheap round trip ticket to Peak Island. Once on the island, rent bikes from Brad's Bike Rental & Repair and explore the 4-mile loop along the coast. Stop at the Island Lobster Company before heading back to the mainland. For another activity, Portland Paddle's Sunset Kayak tour is a nice end to the day, followed by dinner at DuckFat (tourist/popular vibe) or CBG (divey vibe).

Day 3: Brewery hop


Becky's Diner is open from 4am to 9pm, so make sure to fit it into your trip. I recommend their breakfast and their lobster eggs benedict! If breweries are your thing then I would check out the following: Liquid Riot, Austin Street, Après (my personal favorite), Belleflower, Lone Pine (for some funky beer flavors). Make sure to check out Terlingua for dinner and finish the night with one last cocktail at Portland Hunt Club!

Day 4: Island Creek Oyster

Spicy Oysters served

Before making the trip back to the airport, stop at Forage Market for bagels and coffee and head to the Portland Head Light to see the famous Lighthouse and cliff morning walk. Since you will have to backtrack onto the mainland, return to the same area and stop at The Shop by Island Creek Oyster for the best priced oysters in the city! I also tried their trout dip and caviar which were a perfect completion to the trip. While driving back, if time permits - opt to take Route 1 and get a more scenic drive to Boston.

Need to Know

Looking for more travel inspo? Check out my guide, A Week Around Switzerland in Winter. This guide is part of our ongoing series on travel to Portland, Maine.

Advisor - Alanna Zappariello

Travel Advisor

Alanna Zappariello

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This guide is part of our ongoing series on travel to Maine.