Plan Your Chesapeake Bay Sailing Trip

Welcome Aboard!

Based out of Rock Hall, located on Maryland’s Eastern Shore, Shardana Sailing Charters has a large range of cruising options.  We offer half-day, full day, and sunset sailing charters. We also set out on overnight destinations and weekend sailing trips, as well as multi-day cruising charters. Our trips can be laid-back or adventurous; you decide how you want to sail and enjoy Chesapeake Bay. We can design your charter so you can swim, visit an historic sight, anchor out to star gaze and/or enjoy dinner ashore at a restaurant. How you sail on Shardana is (nearly) totally up to you! We can custom design your sailing adventure to meet your specific needs and fulfill nearly any of your requirements. Our 43-foot semi-custom built sailboat can accommodate up to six passengers per trip, including families, friends, groups, or even small office retreats.  We partner with other captained owned and operated sailboats to accommodate larger groups and corporate events.   Sailing on a yacht is a personal and intimate experience and our captains and crew are on board to serve you.    All of our cruises are private sailing charters so you decide with whom you sail and in many ways, how you sail.   If you would like to learn how to sail or improve your skills, Shardana Sailing Charters can provide you with sailing instruction. All of our captains are certified sailing instructors and have sailed in the Caribbean and Mediterranean seas; Some have sailed all over the world. (See our Captains Bios here). You will cherish the life-long memories made sailing on Shardana for years to come.  That's why our motto is Sail Your Story!

Join us on a sailing charter and sail any or all of the 205 miles that mark the northern and southern boundaries of America’s most famous sailing destination and the largest bay in the USA— the Chesapeake Bay!   We can customize any cruise for up to six passengers. All half-day and full-day excursions include soft drinks and snacks.  S/V Shardana has three state rooms, one of which is reserved for the captain.  Therefore, please understand that for groups larger than four people on multi-day cruises, two passengers may be sleeping in the convertible beds located in the main salon.  

 The Chesapeake Bay is the largest estuary in the United States as well as one of the premiere sailing destinations in the world. Below are some of our favorite destinations in the northern and middle Bay, grouped by the duration of a sailing charter from our home base at Osprey Point Marina, 20786 Rock Hall Avenue, Rock Hall, MD 21661.  Rock Hall, commonly referred to as the “Pearl of the Chesapeake”, is a great destination before or after we leave the dock. There are plenty of dining options including our own Osprey Point Inn. We also recommend Blue Heron Oyster House and Inn. How about picking up freshly caught and steamed crabs and enjoying an outdoor picnic? We recommend Fords Seafood and Chester River Seafood.

A Relaxing Quick Getaway?

Come sail for an overnight. We depart anytime you want and return 24 hours later. Sail to historic Annapolis and walk the city; then enjoy dinner at any one of the many restaurants located in town. Alternatively, sail to a quiet cove, make dinner and watch the sun set and enjoy a cocktail while gazing at the stars. Another option is a sail to Worton Creek where we can anchor and then take the dinghy ashore for your own wine tasting at Lands Point Winery and Vineyard. There are plenty of other options/choices for you to experience. Your Captain will be more than happy to help you plan your trip ahead of time.

Multi-Day Charters

Multi-Day trips allow you to sail a little further letting you see and do more on the Chesapeake Bay.  Shardana is fully equipped to anchor in an isolated cove or tie up at a town dock (dock fees are extra).  You can combine any of the above destinations with one of those listed below or many other interesting destinations.  Your personal Captain takes great pleasure helping you plan your itinerary.   Our three most popular trips are our 3 day Chesapeake Bay Cruise, Weekend Special and Mid-Week Special Charters.

Some of our Sample Itineraries

• Kent Island circumnavigation. Friday evening sail to the Magothy River to anchor and grill. Saturday, sail past the iconic Thomas Point Lighthouse and Bloody Point to St. Michaels. Return Sunday via the Kent Narrows.

• Spend the first night on a mooring ball off “ego alley” in Annapolis then set sail the following day to the Corsica River anchorage where you can watch the bald eagles and be surrounded by nature before sailing home the next morning.

• 5-day: Magothy River to Annapolis to St. Michaels to Corsica River and home.

To the north is Chesapeake City, located on the famous Chesapeake and Delaware Canal . The "C&D", as the canal is commonly called by mariners, connects the Delaware River to the Chesapeake Bay, and is considered the northern entrance to the bay.  Multiple anchorages, such as the Bohemian River, Still Pond, Fairlee Creek and Worton Creek are all perfect for gunk-holing.    Cruise up the Sassafras River to dinner in Georgetown, Maryland;  Seeing the wildlife and gorgeous sunsets will take your breath away.  

Annapolis is the capital of Maryland and is the home of the United States Naval Academy. Annapolis has many restaurants and bars, too many to mention here, all within walking distance from the water.  

Historic St. Michaels, on the Miles River, is a 3 or 6-hour sail, depending on whether we take the short cut through Kent Narrows or take the long way under the Chesapeake Bay Bridge and around Bloody Point and up eastern bay. Shardana is a member of the Chesapeake Bay Maritime Museum and you can take advantage of discounted dockage or just tour the museum before dining at one of St. Michaels’ finest restaurants. Staying overnight at the museum is a unique experience. For truly authentic Italian cuisine check out Limoncello, the owners are from Naples, Italy. For some great pizza try the ever popular Avas. There are plenty of other restaurant options as well. If you are a “rum-o-file” visit Lyon Rum Distillery , the only rum distillery located in the entire Chesapeake Bay. There is plenty of quaint public space to stroll and slow down.

Another alternative is to anchor within the Wye River in the Wye River Recreational Area. Want to visit a winery? We can drop anchor off Cascia Vineyards for some wine tasting (weekends or by special arrangement) then bring your favorite wines back to the boat for dinner after a swim in Cox Creek, a creek located within Eastern Bay.  Other interesting options include sailing to the Rhode or West Rivers. If we decide to drop anchor high up the Rhode River we can dinghy into shore, take a 15 minute walk and enjoy some “oom pah pah” at a classic german beer hall called The Old Stein Inn

In addition to the stops listed above,Oxford, Cambridge, are all quaint, Eastern Shore towns on the way to the southern region of the bay.  You can also consider a cruise to Solomons Island at the mouth of the Patuxent River or other areas such as Deal Island or Nanticoke. Visit Crisfield, Americas crab capitol and while there you can take a 45 minute ferry ride to Smith Island.  Longer trips may take us to the southern part of the Chesapeake Bay including many historical towns and waterways in the Virginia portion of Chesapeake Bay. All of our cruises are custom designed for you.  Let your captain know where you want to go, what you want to see and do. He or She will work with you to design your perfect sailing trip.   Whatever itinerary you choose will immerse your body and soul with the sights, sounds, smells and tastes that cruising the Chesapeake Bay has to offer. 

 Ready to sign on? Book your adventure now.