Boothbay Harbor [1] teems with sailing ships. Lazy Jack (Pier One, Boothbay Harbor, 207/633-3444, www.sailschoonerlazyjack.com [2], May–mid-Oct., $28) is a 1947 schooner offering two-hour sails of the harbor. Renowned ocean sailors Herb and Doris Smithhave built five schooners, five of which were named Appledore. The exception is the Windjammer Eastwind (20 Commercial St., Boothbay Harbor, 207/633-6598, www.schoonereastwind.com [3], $25), which sets sail for two-and-a-half-hour cruises to see the seals at Seal Rocks.
The Muscongus Bay is a favorite for sea kayakaing. Midcoast Kayak (47 Main St., Damariscotta, 207/563-5732, www.midcoastkayak.com [4]) rents kayaks ($35–55 for full day) and offers tours ($35–60) allowing you to poke in and out of salt marshes and harbors.
Links:
[1] http://www.moon.com/destinations/new-england/maine/midcoast/southern-midcoast/boothbay-region
[2] http://www.sailschoonerlazyjack.com
[3] http://www.schoonereastwind.com
[4] http://www.midcoastkayak.com