Portland Discovery Land & Sea Tours. The informative trolley tours of Portland Discovery Land & Sea Tours detail Portland's historical and architectural highlights from Memorial Day through October. Options include combining a city tour with a bay or lighthouse cruise. Long Wharf, 170 Commercial St., Portland, ME, 04101. 207/774–0808. www.portlanddiscovery.com. $22.
Greater Portland Landmarks. Take 1½-hour walking tours of Portland's historic West End on Friday from July through 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, ME, 04101. 207/774–5561. www.portlandlandmarks.org. Tours 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 with Maine Foodie Tours. The culinary foot tours include stops at fish mongers, bakeries, and cheese shops that provide product 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. $39.
Portland Freedom Trail. The Portland Freedom Trail offers a self-guided tour of sites associated with the Underground Railroad and the antislavery movement. Portland, ME. 207/591–9980. www.portlandfreedomtrail.org.