01 Jewell Island, Portland
“If you make one stop in Casco Bay, it should be Jewell Island—it never disappoints,” says captain Warner Ogden of Sea Tow Portland. At the island, anchor in Cocktail Cove, the appropriately named hangout for sailors and cruisers alike. Follow wooded trails and climb one of the World War I-era towers for incredible watercolor views, stretching from Cape Small to Cape Elizabeth.
02 Tenants Harbor, St. George
If you ask harbormaster Dave Schmanska about his favorite place to tie up, he’ll answer without hesitation: “Smack dab in the middle of Tenants Harbor—it’s beauty at its finest.” If you can, visit for St. George Days in July to take in a stunning fireworks display over the inner harbor. While you’re there, be sure to look for Southern Island Light, the lighthouse painted by the Wyeths.
03 Upper and Lower Torry Islands, Brooklin
President of Brooklin Boat Yard, Steve White, is partial to a small, unnamed harbor, located just down the road from his business. “There’s a spot I love, between Upper and Lower Torry islands,” says White. “The islands are connected by a sandbar at about half tide—a perfect view for a beautiful moonset.” Private and secluded, you’ll rarely find anyone else around.
04 Jameson Point, Rockland
Rockland Harbor’s charm lies in its size and accessibility, its buzz of activity. If you anchor off in the lee of Jameson Point, you can watch it all at a distance—the barges, ferries, cruise ships, and fishing boats weaving in and out. Harbormaster Ed Glaser agrees: “There’s no better sight than a windjamming schooner skimming the horizon past the breakwater and the lighthouse.”
05 Ellsworth Harbor, Ellsworth
Tucked away from the Atlantic, this pocket harbor is as quaint as the town of Ellsworth. Mooring here is best enjoyed at sunset, when the water reflects the inky silhouettes of pine trees and bobbing docks. Harbormaster Randy Heckman likes to anchor in the waterfront’s outer edges. “If you get out farther,” Heckman says, “that’s where the eagles are. It’s pretty neat to have an eagle for a neighbor.”
06 York Harbor, York
Shingle Style, Colonial Revival, Second Empire—the York Harbor shoreline is a microcosm of historic architecture. Commodore of the Agamenticus Yacht Club, Doug Tuttle, prefers to moor underneath it all by the marina docks. “From this vantage point,” says Tuttle, “you have a front-row view. For a grand vista, row ashore and follow the Cliff Walk, a beach rose-lined path high above the surf.