The Old Port district near the waterfront has original cobblestone streets and is a distinct mixture of funky boutiques, snug coffee shops and enough dining options to satisfy any palette -- from celebrated $6 burritos (Granny's Burritos, 420 Fore Street), to fine dining options (such as Fore Street, 288 Fore Street) to plenty of old-fashioned Irish pubs and seafood/chowder restaurants.
Peaks Island is a short ferry ride from downtown Portland on Casco Bay Lines. With live music in the summer and great roads for walking and biking, you'll get a glimpse into Maine island life. Fall is another great time of year to take in the island foliage. If you're up for a longer boat ride, Casco Bay Lines offers a host of scenic cruises around the Casco Bay, as do smaller operators.
If you're looking for history, check out the Maine Historical Society and the adjacent vintage Wadsworth-Longfellow House, home to Portland-born poet Henry Wadsworth Longfellow, who once described Portland as the "Jewel by the Sea."
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