The captains at South Portland Sailing Center have a knack for sailing not only because of their licensure and training, but also because many of them have called a boat home at some point. They share the expertise they gained from living on and conquering the waters off the east coast with their clients, who can charter a variety of crafts including a gaff-rigged New England Cat and a full-keel cruising boat. After a relaxing ride or a lesson, members can kick back at the park next to the river.
In the 1800s, windjammers and their mighty sails were a frequent sight up and down Maine's coast, where they would pull fish from the water and fill New England's insatiable need for goldfish crackers. By the 21st century, most had abandoned windjammers for engine-powered vessels—but not Hasket Derby Hildreth. A boat builder and mechanical engineer, Hildreth had a vision to re-create the windjammer's classic design on modern shores. Working with a friend who was a boat restorer, Hildreth and his team fashioned their own steel tools and built one of Portland's only engineless windjammers, which they affectionately christened Frances. Maine Sailing Adventures launched Frances in the fall of 2003. Though Hildreth has since passed away, his memory lives on through the legacy Frances continues to perpetuate with each voyage. Today, she can be found at Maine State Pier, where passengers board her shallow deck and sail out to enjoy Maine's scenic coasts without the noise or emissions typical of engine-powered boats. These trips stretch beyond standard tours, though. As they sail, the crew spins tails of Portland's maritime history, teaches passengers how to hoist the topsail, and transforms the boat into a floating classroom, where students can learn about lobster migration and how many wishes they can get from a starfish.
Bubbles break the surface of the water as the beast makes its way upward for a breath of fresh air. Suddenly, her back can be seen atop the waves as her spout releases a geyser-like explosion of air and water. From the decks of Odyssey Whale Watch’s vessels, passengers take in sights such as these and further their understanding of the creatures with the help of an on-board naturalist, who identifies humpback, finback, and minke whale species. His job is made all the easier by the cruise ship’s captain, an experienced mariner who has committed to memory the most densely populated feeding areas for Maine’s massive mammalian residents, which often hang out about 20 miles off shore. In addition to whale-watching tours, Odyssey Whale Watch takes passengers out on deep-sea fishing trips to reel in cod, haddock, and mackerel.
The Boathouse’s team of aquatic experts makes Casco Bay accessible to adventurers of all ages and skill levels by renting out and selling Riviera stand-up paddleboards, which boast a quick response, easy glide, and maneuverability. Their one-hour private paddleboarding lessons empower newcomers to gracefully propel themselves over calm, glassy waters using an oar or an uprooted stop sign. In addition to paddleboards, The Boathouse also sends thrill-seekers splashing through the bay with surf boards, Hobie Cat boats, and various water accessories, such as wetsuits and sailing shorts.
With its archipelago of island communities, Maine needed a way to connect its maritime residents after the system of colonial-era catapults became too expensive to maintain. Enter Casco Bay Island Transit District, also called Casco Bay Lines. The aquatic outfit operates a variety of vessels year-round, transporting passengers between Portland and the islands of Casco Bay. Aside from scenic commuter service, the line also introduces visitors to the storybook sights of the northern New England region, whisking them on music cruises and sunset tours along the kraken-dappled bay.
Surrounding Kennebunkport Marina is a town awash in centuries of nautical history; the community also boasts a spot on AOL Travel's list of the 10 Best Beach Towns in America. The marina contributes to its pristine environs with new docks, an outdoor fireplace, and a riverside courtyard where guests can lounge on adirondack chairs. From the docks, which have hookups for water and 30- and 50-amp service, boaters can captain their vessels down the Kennebunk River or travel one-quarter mile to open ocean waters. Year-round storage keeps ships protected during winter or transatlantic spitball wars, and spring engine commissions by certified technicians prep boats for the sailing season.
Those without their own watercraft can join the Kennebunkport Boat Club, which grants members of any skill level access to a quartet of boats that range from 15 to 26 feet. Additionally, the store offers powerboat, canoe, and kayak rentals, and reservations of the Captain's Cottage make lodgers feel more nautical than tying their shoelaces in bowline knots.