3 Days in Portland, Maine Itinerary | A Long Weekend Guide + Map

Portland, Maine, is a city brimming with coastal flair, historic  buildings, and the small-town charm worthy of an epic New England getaway.

This port city is dotted with excellent eateries and bars, as well as  art galleries on every corner, and gives you easy access to southern  Maine beaches and state parks.

I unpack the best ways to explore this charming city through an extensive Portland, Maine weekend getaway 3-day itinerary.

Everyone knows a good adventure starts with a delicious cup of coffee and a tasty breakfast.

Source: Coffee By Design

Coffee + Breakfast

Once you’re pumped on caffeine, hop on the first ferry to Casco Bay. You can catch a gorgeous sunrise via a cruise or a mailboat run at 10 am.

Cruise or Mailboat to Casco Bay

Source: Canva

Upon returning to the mainland, stroll down Commercial Street, and discover some of the best spots in Portland, Maine.

Walk from Commercial Street to Old Port

After all that walking, you must be famished. Head down to  Little Tap House on High Street from Old Port for local delights.

Lunch at Little Tap House

A skip away from Little Tap House, you’ll stumble upon the Portland Observatory. The maritime signal tower is the country’s only surviving one of its kind.

Portland Observatory Tour

Source: Canva

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