Why linger in beach traffic when you can board a boat and cruise the open water? Anchored close to the Square, Community Boating Boston (community-boating.org) offers an assortment of lessons on the Charles River, from amateur-level courses to specialized racing and windsurfing programs for seasoned sailors. While classes require membership, novices can also dip in for a non-membership daylong kayak or sailboat rental.
Boston Sailing Center (bostonsailingcenter.com) leaves from Lewis Wharf in the North End, with gorgeous skyline waterfront views. Newcomers can explore the harbor with introductory courses, while ambitious sailors can learn how to charter cruises, sail at night, and navigate coastal passages. The center also maintains a robust social calendar, with members’ regattas and mixers.
In Charlestown, Blackrock Sailing School (blackrocksailingschool.com), which also hosts a marina in Warwick, Rhode Island, offers an immersive experience: Book multi-day, overnight lesson packages focusing on coastal cruising, catamarans, and more, including trips to the Caribbean. For bundled packages in a tropical locale, check out East Boston’s First Reef Sailing (firstreefsailing.com): They offer 5- and 7-day American Sailing Association- certification classes on trips to the U.S. and British Virgin Islands (with pauses to sightsee, of course), plus the opportunity to charter your own cruise once certified.
Is rowing more your speed? Riverside Boat Club (riversideboatclub.com) is the hub for proficient rowers: They don’t offer classes, but they do maintain a busy roster of training programs for men, women, and junior rowers on the Charles—including some who train for Head of the Charles and even the Olympics. Still getting your feet wet? Consider a class with the approachable staff at Community Rowing Inc. (communityrowing.org), which offers intro to rowing and sculling classes, including para-rowing classes for athletes with disabilities. They also host corporate and team-building programs on the Charles. If you’d rather just enjoy the ride, book a luxury yacht through Marblehead’s Carol Kent Yacht Tours (carolkent.com), which tailors customized, luxury itineraries for groups from New England to the South Pacific—as well as to exotic locales like Antarctica. For a sightseeing trip closer to home, book an Acadian Boat Tour (acadianboattours.com) out of Bar Harbor, Maine, which offers classic themed group cruises, focusing on lighthouses or sunset wildlife. They also run private family outings for fishing, fjord tours, and even ash-scattering trips for memorial celebrations.
For a more relaxing—and nourishing—experience, check into Bed & Breakfast Afloat at Charlestown’s Constitution Marina (bedandbreakfastafloat.com): Rent a well-appointed yacht or houseboat, sip drinks on your private deck at sunset, and wake up to breakfast in the morning. It’s close to dry-land attractions, too, like the USS Constitution Museum and Encore Boston Harbor.
If you’re hoping to give your favorite vessel a facelift, visit South Shore Boatworks (southshoreboatworks.com) in Carver, which specializes in repairing hulls and interiors. Their marine carpenters also craft custom steering wheels and even design nautical furniture, from wooden toy keepsake boats to deck chairs. On the North Shore, duck into Lowell’s Boat Shop (lowellsboatshop.org) in Amesbury, known for custom-built dories. They’re also home to kids’ and adults’ nautical carpentry classes, boat-building apprenticeships, boat refurbishment programs, and refurbished skiffs for purchase.
Last but not least, a sailor needs the right style. Visit Harwich’s J.M. Byron House for a trove of maritime-themed décor treasures (thejmbyronhouse.com), or duck into Sara Fitz in York, Maine, for nautical knickknacks, from trays and glassware to sailboat wallpaper.
Outfitting a small seafarer? Shop Belmont’s Red Wagon (theredwagon.com) for a cute line of nautical-themed kids clothing. Grown-up sailors should browse the wares at the Sault (saultne.com), with outposts in the South End and Portsmouth, NH: Their beachy tops, tunics, and salt-scented candles evoke the ocean air no matter what the weather.
