Various Portland-based skippers offer whale-, dolphin-, and seal-watching cruises; excursions to lighthouses and islands; and fishing and lobstering trips. Board the ferry to see nearby islands. Self-navigators can rent kayaks or canoes.
Casco Bay Lines. Casco Bay Lines operates ferry service to the seven bay islands with year-round populations. Summer offerings include music cruises, lighthouse excursions, and a trip to Bailey Island with a stopover for lunch. Maine State Pier, 56 Commercial St., Portland, Maine, 04101. 207/774–7871; www.cascobaylines.com.
Lucky Catch Cruises. Set sail in a real lobster boat: this company gives you the genuine experience, which includes hauling traps and the chance to purchase the catch. Long Wharf, 170 Commercial St., Portland, Maine, 04101. 207/761–0941; www.luckycatch.com.
Odyssey Whale Watch. From mid-May to mid-October, Odyssey Whale Watch leads whale-watching and deep-sea-fishing excursions. Long Wharf, 170 Commercial St., Portland, Maine, 04101. 207/775–0727; www.odysseywhalewatch.com.
Portland Discovery Land & Sea Tours. For tours of the harbor and Casco Bay in a boat or on a trolley, including an up-close look at several lighthouses, try Portland Discovery Land & Sea Tours. Long Wharf, 170 Commercial St., Portland, Maine, 04101. 207/774–0808; www.portlanddiscovery.com.
Portland Paddle. Run by a pair of Registered Maine Guides, Portland Paddle leads introductory sea kayaking clinics along with guided trips between the Casco Bay islands June through September. Two-hour sunset paddles ($38) are a fave, but the most unique offering involves a four-hour paddle to the abandoned island military installation of Fort Gorges ($65), where you'll enjoy a short acoustic concert before heading back. Kayak and paddleboard rentals are available. Eastern Promenade, East End Beach, off Cutter St., Portland, Maine, 04101. 207/370–9730; www.portlandpaddle.net. Closed Nov.–May. Oct. by appt. only.
Portland Schooner Co.. May through October this company offers daily windjammer cruises aboard the vintage schooners Bagheera and Wendameen. You can also arrange overnight trips. Maine State Pier, 56 Commercial St., Portland, Maine, 04101. 207/766–2500; www.portlandschooner.com.