Several car-rental options exist at the Portland Jetport; others are dispersed around the South Portland area, just outside the main city limits.
Congress Street leads from I-295 into the heart of Portland; the Gateway Garage on High Street, off Congress, is a convenient place to leave your car downtown. North of Portland, U.S. 1 brings you to Freeport's Main Street, which continues on to Brunswick and Bath. East of Wiscasset you can take Route 27 south to the Boothbays, where Route 96 is a good choice for further exploration. To visit the Pemaquid region, take Route 129 off U.S. 1 in Damariscotta; then pick up Route 130 and follow it down to Pemaquid Point. Return to Waldoboro and U.S. 1 on Route 32 from New Harbor.
In Portland, metered on-street parking is available at 25 per half hour, with a two-hour maximum. Parking lots and garages can be found downtown, in the Old Port, and on the waterfront; most charge $1 per hour or $8-$12 per day. If you're shopping or dining, remember to ask local vendors if they participate in the Park & Shop program, which provides an hour of free shopping for each vendor visited.