The Eastern Prom offers sweeping views of the harbor and neighboring islands. There is also a foot path along the waterfront that connects to Back Cove and downtown Portland.
A few of our favorites are Duckfat (New American/comfort food), Eventide Oyster Co. (seafood), Becky's Diner (authentic New England diner that's great for breakfast/lunch), Luke's Lobster (great spot for lobster (duh) on the water), and Central Provisions (fun place with a variety of options).
There are many great micro-breweries in Portland - Austin Street is our favorite one. Some others nearby are Rising Tide and Lone Pine Brewing.
Home to many great shops, restaurants, and bars, the Old Port can easily be explored on foot in an afternoon. Leave room for a stop at the Holy Donut on Commercial Street.
If you want to get out of Portland, Fort Williams is about a 10 minute drive away and home to the most photographed lighthouse in the world! P.S. Will took Lauren here on a date the first time she visited Maine.
There is a 3.5 mile foot path around Back Cove that is excellent for running and walking. The path can also be connected to the Eastern Prom and downtown Portland at the exit under the I-295 bridge.