Portland Discovery Land & Sea Tours. The informative trolley tours of Portland Discovery detail the city's historical and architectural highlights, Memorial Day–October. Options include combining a city tour with a bay or lighthouse cruise. Long Wharf, 170 Commercial St., Portland, Maine, 04101. 207/774–0808; www.portlanddiscovery.com. From $14.
Greater Portland Landmarks. Take 1½-hour walking tours of Portland's historic West End on Friday, July–September, with Greater Portland Landmarks. Tours past the neighborhood's Greek Revival mansions and grand Federal-style homes begin at the group's headquarters and cost $10. You can also pick up maps for self-guided tours of the Old Port or the Western Promenade. 93 High St., Portland, Maine, 04101. 207/774–5561; www.portlandlandmarks.org. From $10. Tour at 11.
Maine Foodie Tours. Learn about Portland's culinary history and sample local delights like lobster hors d'oeuvres, organic cheese, and the famous Maine whoopie pie. The culinary foot tours include stops at fishmongers, bakeries, and cheese shops that provide products to Portland's famed restaurants. From summer into early fall, you can also take a chocolate tour, a bike-and-brewery tour, or a trolley tour with a stop at a microbrewery. Tours begin at various locales in the Old Port. 207/233–7485; www.mainefoodietours.com. From $55.
Portland Freedom Trail. The Portland Freedom Trail offers a self-guided tour of sites associated with the Underground Railroad and the antislavery movement. Portland, Maine. 207/591–9980; www.portlandfreedomtrail.org. Free.