If You Have 1 Day
Spend the morning wandering the streets and shops of the Old Port. Break for a harborside lunch along Commercial Street. In the afternoon, hit the museums in the Arts District. Architecture buffs will want to take a drive or stroll through the West End neighborhood. End the day with a drive up Congress Street to the Eastern Promenade for sweeping hilltop views of Casco Bay.
If You Have 3 Days
Spend your first day in the Old Port and the Arts District. Art lovers will want several hours inside the Portland Museum of Art. Take an hour or so to walk the West End neighborhood, with its stunning Colonial Revival and Victorian homes, then head to Hadlock Field for a baseball game or spend the night downtown. On your second day, take a morning boat ride to Eagle Island or another Casco Bay island. In the afternoon, drive to Cape Elizabeth and visit Portland Head Light and Two Lights. Return to Portland for the night. On your third day, head north to Freeport, where you can shop at various outlets and L.L.Bean.
If You Have 5 Days
Spend your first two days in Portland. Be sure to linger in the Old Port and stroll through the architectural splendor of the West End. You can leave your car at your hotel for both days and easily get around on foot. See the islands via a Casco Bay Lines ferry, vintage schooner, whale-watch or other theme cruise, or opt for a sportfishing adventure.
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On Day 3 take a ferry to one of the islands in Casco Bay and prepare to relax. You’ll have left your car in Portland; rent a bicycle on the island or just explore its quiet roads (many of which are unpaved) by foot. Take a guided kayak trip; or sign up for a golf-cart tour. Grab dinner on the island or head back to Portland.
On Day 4 head out in your car for several hours of touring, including a visit to nearby Cape Elizabeth to see Portland Head Light. The park is a great place for a picnic lunch. Continue your scenic drive, stopping at any of several state parks for hiking and beachcombing, before making your way to Prouts Neck. Here you can stroll along the Cliff Walk. Head back to the interstate and continue north to Freeport for some shopping at L.L.Bean.
Spend Day 5 browsing the outlets, hiking through Wolfe’s Neck Woods State Park (for beautiful sea views, including osprey nests), or taking a scenic harbor cruise. On the way back to Portland, stop at Day’s Crabmeat & Lobster in Yarmouth for a bona fide Maine lobster roll.