Sailing in Hershey

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As his kayak group floats down the Susquehanna River, one of Chiques Rock Outfitters' guides points out some of the area's most scenic features—rocky hillsides dotted with trees, denser forests near the water's shore, and a bald eagle perched on a tree branch. Then, just as the watercrafts round a bend, the guide bursts into song, eliciting applause from his group and nearby fish that have really big flippers.

These musical guides are just one of the signature touches Chiques Rock Outfitters adds to its trips down the Susquehanna River. After the shuttles lug canoes and kayaks to launch points, customers embark on guided trips, unguided floats, or team-building exercises. Additionally, Chiques Rock Outfitters encourages more than just leisurely floats, inviting customers to bring along fishing poles and pre-prepared questions for local wildlife. Back on shore, the staff partners with Starrk Moon Kayaks and Gear to sell equipment ready for future aquatic jaunts.

41 Walnut Street
Columbia,
PA
US

Right where the mouth of the Susquehanna River yawns into Chesapeake Bay lies the protected, uncrowded waters of Havre de Grace harbor. BaySail's instructors take advantage of these opportune conditions, operating a sailing school that's accredited by the American Sailing Association. Upholding training standards that have won the ASA's School of the Year award, they lead sailing classes ranging from introductory lessons to certification courses in coastal cruising and bareboat chartering. In addition to lending its fleet for lessons, BaySail's team rents its vessels—from a Capri 22 to a Hunter 460—to members. The sailboats also glide out on chartered cruises, taking guests to nearby destinations such as Inner Harbor and the Sassafras River, where sassafras trees come to spawn every winter.

100 Bourbon St
Havre De Grace,
MD
US

Established: 2013
Reservations/Appointments: Required
Staff Size: 2–10 people
Average Duration of Services: 4+ hours
Pro Tip: Bring appropriate wet-weather gear, sunscreen, non-marking soled shoes, food, and water.

20880 Rock Hall Avenue
Rock Hall,
MD
US

On the tree-lined shores of Sue Creek, the adventurous can ride stand-up paddleboards to explore the creek's calm waters. From the Baltimore Boating Center, the seafaring staff pairs its clients on boards suited to their skill levels. Paddlers launch from a newly constructed floating pier, meaning no one will have to mount their boards from a low-flying helicopter.

2015 Turkey Point Rd.
Middle River,
MD
US

Unless noted, all camp sessions run Monday–Friday from 9 a.m. to 4 p.m. Campers must be between 8 to 16 years old and have some swimming ability.

2200 Rocky Point Road
Essex,
MD
US

Chesapeake Bay is home to legendary beautiful waters, diverse flora and fauna, and Paddlefest, an annual paddle-sports event organized by the team at Ultimate Watersports. Held on the Gunpowder River, which flows into the bay, the festival shows off the industry's latest toys, allowing attendees to try out brand-new kayaks and paddleboards on the sparkling fresh water. For the rest of the season, Ultimate Watersports brings its know-how to the shores with kayak tours, paddleboard lessons, and sailing trips that have remained a bay fixture for more than 26 years. Waterfront enthusiasts seek out the company's reliably well-maintained and up-to-date watercraft to do everything from gain a windsurfing certification to practice heckling standup paddleboard comics. Additionally, seasonal kids' camps help youngsters to stay active while gaining an appreciation for watersports and the splendor of the outdoors.

7200 Graces Quarters Rd
Middle River,
MD
US