Drop an Anchor

One of the best parts of cruising Maine’s coast is discovering new coves and inlets to spend a night (or just an afternoon). Find your next anchorage with these suggestions from a few expert boaters.

Hell’s Half Acre in Merchant’s Row | Penobscot Bay
An archipelago of more than 50 islands between Deer Isle and Isle au Haut, Merchant’s Row is a boater’s paradise. One of the smaller islands, Hell’s Half Acre, which has granite ledges that are great for jumping into the ocean and swimming, is the favorite anchorage of Brian Harris, general manager of Maine Yacht Center in Portland. The island has a camping area and is part of the Maine Island Trail Association’s 375-mile water trail.

Sand Island | Casco Bay
Located off Chebeague Island, Sand Island is a favorite of the crew at Yarmouth Boat Yard and Freedom Boat Club of Maine. The island, small enough to walk from end to end, features a large sandy beach area and 360-degree views of the surrounding islands in Casco Bay.

Cocktail Cove | Casco Bay
Another recommendation from the crew at Yarmouth Boat Yard and Freedom Boat Club of Maine, Cocktail Cove is a natural harbor off Jewell Island in Casco Bay. The popular hangout for sailors and cruisers is ideal for swimming and is the best anchorage to reach Jewell Island and its three miles of trails.

Damariscove Island | Near Boothbay Harbor
This uninhabited 210-acre island is located six miles off Boothbay Harbor. Owned and managed by the Boothbay Region Land Trust, the island features stunning ocean views, two courtesy moorings, a beach, and two miles of easy hiking trails. Damariscove is historically significant, having been a fishing settlement for the Abenaki and later European settlers, and has a small museum with information about the island’s history.

Start Sailing

Learn the ropes at SailMaine and other sailing programs around the state.

Searching for a hands-on hobby that both gets you outside and ups your lifestyle cred? Maybe it’s time to put those boat shoes to use and check out a sailing class. Whether you’re someone who’s never set foot on deck or you just need a reminder of the difference between a halyard and a sheet, SailMaine’s community sailing center based on the Portland waterfront provides affordable classes, charters, rentals, and even races from June to October on Casco Bay. “Maine is one of the best places to sail on this planet—and I’ve sailed a lot of really wonderful places,” says Alicia Witham, SailMaine’s former director of adult programs and charters, who is now the executive director of the Carpenter’s Boat Shop in Pemaquid.

SailMaine’s adult sailing program, which provides revenue that supports the organization’s youth and high school sailing programs, offers beginner, intermediate, and refresher courses on J/22s, a 22-foot boat that’s known for being easy to rig, responsive, comfortable, and dry for its size. New to the program this year are Learn to Sail and Learn to Cruise courses on SailMaine’s recently acquired 40-foot catamaran, the Rip Van Winkle. The charters, which host up to six passengers and come with a professional captain (who will teach you as much or as little as you’d like to know), can be as short as one hour to as long as three days and two nights, perfect for a “sail-cation.”

Already certified and just want to rent a boat? Anyone can charter the J/22s as long as they demonstrate they can sail. SailMaine offers both half-day and full-day rentals seven days a week between Memorial Day and Labor Day. One of the program’s best kept secrets is the PortPass, a $700 season pass that gives experienced sailors unlimited access to the J/22s for the entire sailing season, meaning more opportunities to experience Maine’s largest city from an aqueous vantage point.

Where to Learn to Sail Around Maine
The Apprenticeshop | Rockland
apprenticeshop.org

Boothbay Harbor Yacht Club | Boothbay Harbor
bhyc.net

MDI Community Sailing Center | Southwest Harbor
mdisailing.org

South Portland Sailing Center | South Portland
southportlandsailingcenter.com

WoodenBoat School | Brooklin
thewoodenboatschool.com

Sea Stays

As the old saying goes, “The two happiest days in a sailor’s life are the day they buy a boat and the day they sell it.” While we like to think boats have gotten a bad rep as “money pits,” there are plenty of Mainers—and visitors to Vacationland—who don’t own their own vessels. These are a few of our recommended boats to book for a unique water stay, no experience required.

Maine Windjammer Association
If a windjammer cruise isn’t on your bucket list, it should be. These tall-masted, multi-sailed schooners can be spotted from late spring to early fall up and down the Maine coastline. Not only can you stay on one, but you can even help steer the ship. The Maine Windjammer Association offers three-, four-, and six-day charters that set sail from either Camden or Rockland. Aboard one of the fleet’s eight vessels, several of which were built in the nineteenth century (the Lewis R. French is America’s oldest merchant sailing ship and turns 150 this year), swap out your plugged-in life for a few days of pure sail, salty air, downeast fare, and some astonishing celestial scenes. The price includes meals, from freshly baked scones and biscuits to chowders and curries, fresh salads, and, of course, lobster bakes. Hot tip: bring binoculars for a chance to spot seals, osprey, puffins, and maybe even a whale.

Sebasco Harbor Resort
Hoping for a more private charter? Bay Dreamer, the newly acquired and pristinely renovated 47-foot Sabre motor yacht at the Sebasco Harbor Resort in Phippsburg, is equipped with a kitchen, salon, and two luxurious cabins, each with its own bathroom, and is available to book for four-hour cruises, overnights in the harbor, and even 24-hour destination trips to Boothbay or Portland. Captain Phil Luedee, who has been hanging around the Sebasco—and boats—since he was toddler, is happy to provide whatever experience you’re looking for, whether it’s a luxurious happy hour on the water in Casco Bay, swimming in the coves of the New Meadows River, or motoring to an island on the Maine Island Trail.

Derecktor Robinhood
Maybe you’d rather be completely alone out on the water, no captain and no boating experience required. The Riggs Cove Rentals at the Derecktor Robinhood in Georgetown offer three moored houseboats with fully equipped galleys (sailor talk for kitchens), a full-size shower, central heating, barbeque grills, and even two kayaks for exploring the cove. All three boats contain a private queen berth stateroom, and accommodations for four—the Nancy Lou (above) and the Charles Andrew have an extra settee in the main cabin allowing for sleeping for five. The marina has a three-night minimum, but between motoring your skiff to the on-site Anchor Bar and Grill, exploring the nearby communities of Five Islands and Bath, and hanging on the deck to enjoy the sunset with the sound of waves lapping at the hull, you’ll be plenty occupied on your own “floating island.”