Sailing in Havre de Grace

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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

RIB Adventure Tours conduct informative history tours and scavenger hunts around Baltimore Harbor, even when the horizon becomes a blur; all tours take place aboard 26-foot-long rigid, inflatable speedboats. Built to Navy SEAL specifications by a local Massachusetts boat manufacturer, the boats keep riders secure aboard jockey seats. On guided history tours, passengers snag high-speed glimpses of harbor landmarks including lighthouses and forts, whose history guides can expound upon. During scavenger hunts, guides prompt passengers to look for environmental clues and give individual scores. Captains and tour guides brief passengers on safety before all excursions and supply them with high-grade waterproof cameras to take pictures of passing scenery.

More relaxed cruises from partner Hestia Cruises, onboard the 32-foot sailing yacht Hestia, might drift past the USS Constitution or out into the outer harbor. The ship is manned by a captain, a full crew, and friendly cocker spaniel named Ensign. Guests can help with the sailing duties, but padded seats and a BYOB policy for those of age may encourage them to sit back and relax.

40 International Drive
Baltimore,
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 Road
Middle River,
MD
US