Cruise the Chesapeake
Plan Your Itinerary
Shardana Sailing Charters, based out of Rock Hall on Maryland’s Eastern Shore, 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 customize each trip to best meet your expectations but here are some examples of our common trips.
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).
Half-Day and Full-Day Trips:
Our half-day and full-day sailing charters offer the chance to raise the sails and experience the relaxation of a sailboat and the beauty of a sunset. It only takes 15 minutes to leave the dock and start sailing in the open bay. On a full-day charter, we can go to a quiet anchorage for lunch and a swim, stop at a waterside restaurant like Harris Crab House at Kent Narrows or The Point Crab House and Grill on the Magothy River. Of course. you can simply sail all day with lunch aboard in our spacious cockpit.
Sunset Charter
Experience a tranquil 3-hour sunset sail with us. Bring along your favorite wine and cheese to savor as you witness the sun saying “good night”. Chesapeake Bay's breathtaking sunsets will soothe your soul and bring serenity to all who have the privilege to experience them.
Overnight and Multi-Day Sailing Trips
Our multi-day trips can be laid-back or adventurous; you decide how you want to sail and where you want to go on the Chesapeake Bay. We can design your charter so you can swim, visit a 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! Shardana is fully equipped to anchor in an isolated cove or tie up at a marina (dock fees are extra). You can explore many of the destinations listed below or choose other interesting locations. Your personal captain will take great pleasure helping you plan your custom itinerary. Our experienced captains are USCG Licensed, certified sailing instructors and have sailed all over the world. (See our Captains Bios here). They will work with you to find the destinations you will enjoy.
Some of our Sample Itineraries
2-Day, 1-Night Cruise
Needless to say, we can’t get too far on a one-day trip and suggest a 2-4 hour sail to an isolated anchorage to enjoy the night “on the hook”. We often set the destination the day of the trip based on the weather and always try to accommodate your preference.
Worton Creek, north of Rock Hall, offers incredible sunsets and nice swimming with some shoreline walking or a visit to the Lands Point Winery.
The Magothy River on the Western Shore has several anchorages with beautiful views and some shore access.
We can sail southeast around Eastern Neck National Wildlife Refuge on the Chester River and drop the hook up the Corsica River. We will likely have the river to ourselves, especially on a weeknight.
3-Day, 2-Night Cruises
Our two most popular trips are the 3-day Chesapeake Bay Cruise and the Weekend Special and each offers many options:
Kent Island circumnavigation. Friday evening sail to the Rhode River to anchor and enjoy a BBQ dinner (ask about our grilled rockfish recipe). Or spend the first night on an “ego alley” mooring ball in Annapolis and go to shore for anything from fine dining to barhopping. On Saturday we will sail past the iconic Thomas Point Lighthouse and Bloody Point to historic St. Michaels. Return to Rock Hall on Sunday through Kent Narrows and be home by lunch.
Spend the first night at the Corsica River anchorage where you can watch bald eagles and be surrounded by nature. On day-two, we’ll take the long way around Kent Island to Dividing Creek on the Wye River before sailing home the next morning through Kent Narrows.
There are multiple other anchorages, such as the Bohemian River, Still Pond, Fairlee Creek and Worton Creek that are all perfect for gunk-holing and eagle watching.
5-Day, 4-night Mid-Week Special Charters
Our longer trips can include all of the above plus some places further afield.
A trip up the Northern Bay can get us out of the Chesapeake Bay! We would likely stop at Worton Creek the first night then leave the bay and enter the famous Chesapeake and Delaware Canal. The "C&D", as the canal is commonly called by mariners, connects the Delaware River to the Chesapeake, and is considered the northern entrance to the bay. The canal can be a unique experience with fast currents and huge ships rumbling by. The Chesapeake Inn is a great place for dinner. We can then head west up the Susquehanna River to visit Havre de Grace for the night. Our next stop would take us back across the Bay and up the Sassafras River to Georgetown, MD with dinner reservations at the Kitty Knight House, an 18th century home saved from being burned by the British by a young woman full of chutzpah. Finally, we’ll have about 6 hours to sail out of the river and back down the Bay to Rock Hall.
A Middle-Bay trip can hit all the spots discussed in the shorter-trip description. 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. Shardana usually takes a mooring ball and clients can either take the water taxi to shore or ask the captain to dinghy them in.
For a more southernly trip, we can visit Oxford, Cambridge and Beyond. Oxford and Cambridge are all quaint Eastern Shore towns on the Choptank River. We could combine that with a stop in St. Michael’s by anchoring in the San Domingo Creek on the back side of town instead of the crowded marinas and anchorage on the Miles River. You can also consider a cruise to Solomons Island at the mouth of the Patuxent River. This would involve a couple of longer sailing days, but it can fit into a 5-day itinerary.
6-7 Day Trips
Our longer trip may include even more variety. We’ll pass some of the spots mentioned above on the way to other areas such as Deal Island or Nanticoke. We can nose up the Potomac River to visit St. Mary’s, the first English settlement in Maryland. Crisfield is America’s crab capitol and while there you can take a 45-minute ferry ride to Smith Island for a slice of their famous cake. Longer trips may include historic towns and waterways in Virginia like Onancock or Jamestown. If you really wanted to push hard, we could even make it to Norfolk, but that would require several long sailing days and would be up to the captain’s discretion.