As much of the country battles the latest polar vortex brought on by a blast of Arctic air, it’s easy to daydream about summer’s inevitable arrival. Maryland’s sprawling, peaceful Chesapeake Bay is, of course, best known for its many marinas and sailing communities. Thus, the Osprey Point team would like to shine a light on three Maryland sailing charters, all of which are located right here in Rock Hall, the “Pearl of the Chesapeake.”

An Unforgettable East Maryland Sailing Voyage

Before we know it, spring will give way to summer’s golden hearth, providing nothing but clear, sunny skies and idyllic temperatures set in the upper 70s and low 80s. The Chesapeake Bay itself spans nearly 4,500 square miles, allowing an innumerable number of sailboats to survey its aquatic terrain. Thankfully, Osprey Point Marina is home to one of Maryland’s finest sailing charters, Shardana. In fact, Osprey Point is within walking distance of two of the state’s most beloved charters. The time to book an excursion is now before availability washes away. But first, please read more about Rock Hall’s top three sailing experiences.

1. Shardana Sailing Charters

Osprey Point Marina’s very own Shardana Sailing Charters remains one of the region’s most intimate excursions. These “luxury-based” adventures offer something that most East Maryland sailing charters simply cannot: sheer privacy. Shardana, a custom-built, 42-foot sailboat, ushers families and small groups out to sea en route to Chesapeake Bay’s quietest, most picturesque locales. Choose between a half-day, full-day, or sunset charter. Because Shardana encourages a “BYOB” atmosphere, sailors can bring along a bottle of fine wine, a growler of craft beer, or a small cooler filled with hard seltzers. And, once the journey is over, you’ll only be steps from your historic accommodation.

2. Blue Crab Chesapeake Charters

Onboard Photo of a Blue Crab Chesapeake Charter. Plan a Maryland Sailing Adventure Today!

Blue Crab is located on the other side of town inside Rock Hall Landing, home to Waterman’s Crab House. While Blue Crab does offer a wide variety of cruises, most curious travelers cannot resist the 90-minute, $35 trip. Twenty-plus years in the making, the Blue Crab team has perfected its touristy appeal. “Island Girl,” a 43-foot center cockpit sailboat, hosts everything from weddings to classic sunset sails and the “cruise-n-crabcake.”

3. Haven Charters

Neighboring Haven Harbour Marina is home to Haven Charters, Maryland’s premier self-guided sailing voyage. Because Haven is a bareboat operation, you’ll need recent sailing and navigational experience, as well as references. What makes Haven Charters even more unique is that they boast approximately 25 vessels, ranging from $1,475 to $2,900 for a two-day weekend trip. Most folks survey the Chesapeake Bay by day and return to Osprey Point in the evening hours for dinner and a good night’s sleep.

Looking for a kid-friendly alternative? Try a public sail via Chestertown’s Sultana Education Foundation.

Historic Accommodations in Rock Hall, MD: Osprey Point

Photo of Osprey Point Marina. Plan a Maryland Sailing Adventure Today!Start and finish each day of sailing, shopping, and sightseeing at Osprey Point, home to the area’s best restaurant, prettiest marina, and most historic lodgings. Immediately following an afternoon at sea, return to Osprey Point Restaurant for a casual yet refined dining experience complete with award-winning vino, coastal cuisines, and homemade desserts. Travelers can choose between an eclectic mix of accommodations, including a farmhouse, uniquely-designed guest rooms, and a bayside annex.

To book a long-overdue summertime sailing escape to sunny Maryland’s cutest small town, please check availability online.