A major international port and a working harbor since the early 17th century, the Old Port bridges the gap between the city's historical commercial activities and those of today. It is home to fishing boats docked alongside whale-watching charters, luxury yachts, cruise ships, and oil tankers from around the globe. Commercial Street parallels the water and is lined with brick buildings and warehouses that were built following the Great Fire of 1866. In the 19th century, candle makers and sail stitchers plied their trades here; today specialty shops, art galleries, and restaurants have taken up residence.

As with much of the city, it's best to park your car and explore the Old Port on foot. You can park at the city garage on Fore Street (between Exchange and Union streets) or opposite the U.S. Custom House at the corner of Fore and Pearl streets. A helpful hint: look for the "Park & Shop" sign on garages and parking lots and get one hour of free parking for each stamp collected at participating shops. Allow a couple of hours to wander at leisure on Market, Exchange, Middle, and Fore streets. The city is very pedestrian-friendly. Maine state law requires vehicles to stop for walkers in crosswalks.