Cruise the Chesapeake

Plan Your Itinerary

Based out of Rock Hall, located on Maryland’s Eastern Shore, Shardana Sailing Charters has a large range of cruising options. The Chesapeake Bay is the largest estuary in the United States as well as one of the premiere sailing destinations in the world.  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.  All of our captains are certified sailing instructors and have sailed all over the world. (See our Captains Bios here).

Overnight Cruise

Enjoy an overnight sail with us. Depart whenever you like and return the next day. Choose to sail to historic Annapolis or St. Michaels, explore ashore and dine at a restaurant. Alternatively, sail to a quiet cove for sunsets, cocktails and dinner under the stars. Many other options are available, and your Captain will gladly assist you in planning your trip.

Multi-Day Sailing 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 the 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.  

Visit Annapolis

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.  

Visit St. Michaels

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

Visit Oxford, Cambridge and Beyond

In addition to the stops listed above, Oxford and 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. 

 Ready to sign on? Book your adventure now.