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“Sail Your Road” – Shardana Sailing Charters

“Sail Your Road” – Shardana Sailing Charters


“Sail Your Road” – Shardana Sailing Charters


Start: Rock Hall, MD

Finish: Magothy River

Distance: 3 days, 4 stops



Rock Hall, MD

39.1382° N, -76.2350° W

As you arrive at the Osprey Point Marina in Rock Hall, MD., excited for your sailing “road trip” on Shardana, any tension that may run through your mind will begin to soften. Park your car and walk over to Dock B, slip 38, and you will find your Captain and crew ready to assist you in boarding Shardana, a 42-foot custom built sailboat.

After securing your gear, participating in a safety briefing, and a walk-through of the many enhancements below and above decks to make your sail sweeter, Shardana will slip her lines and make her way into the stunning Chesapeake Bay.

On Shardana you can participate in the sailing as a spectator or as part of the crew–your call! We want you to “Sail Your Story”. As you reach the Bay, your U.S.C.G. licensed Captain will explain how to hoist and set sails–mainsail first and then the gib–slowly falling off to allow the world-famous winds of the Bay to gracefully carry you to your first destination.

“I love to see and feel the stress leave everyone’s faces as the sails fill and engine goes off. There is nothing quite like the quiet movement through the water with the wind in your face.” –Captain Andrew




St. Michaels, MD

38.7854° N, -76.2233° W

On this voyage, we will be heading to St. Michaels. Depending on the prevailing winds of the day, the Captain will select to either sail under the Chesapeake Bay Bridge, then tacking or gybing to round Bloody Point Light, head across Eastern Bay, and into the glorious Miles River. If the winds drive you more east from Rock Hall, the Captain will sail past the Eastern Neck National Wildlife Refuge to port and cross the Chester River, reaching Eastern Bay via the more complex route under the drawbridge at Kent Narrows. The choice is in part made by the direction of the winds, the current level of tides, and weather. Upon arrival, the Captain will drop anchor for your visit to one of the most famous and prettiest towns on the Eastern Shore–St. Michaels. Once the hook is set, perhaps you’ll want to take a swim off the decks of Shardana, shower on board, and then be ferried to the town dock via Shardana’s hard-bottom inflatable. You can go for a great dinner and walk about the historic neighborhoods in town or return to the boat where the grill will be fired up for you to BBQ a wonderful dinner in the cockpit. At any point, you may be graced with a captivating historical narrative; Shardana is, after all, a certified Chesapeake Bay Storyteller participant.

“Best way to beat the summer heat? Jump off the back of a sailboat into the refreshing waters of the Chesapeake Bay.” – Captain Thad




Annapolis, MD

38.9784° N, -76.4922° W

After spending a peaceful night rocking gently at anchor, you will awake to fresh-brewed coffee after which you’ll prepare breakfast or enjoy a pre-breakfast swim. Once relaxed, fed, and ready, Shardana will raise her anchor, and you will make your way back into Eastern Bay. If the winds are favorable, the Captain will set sail, perhaps using our Code “0” head sail, which allows Shardana to sail the very lightest of winds. 

Relax on the Lido deck as you head west by north to Annapolis, the capital of Maryland, the home of the United States Naval Academy, and sailing center of the Eastern U.S. (some would say the world). Once you arrive in Annapolis, the crew will grab a mooring ball and secure Shardana for your overnight visit.

Dinner can be made on board, or you can again be ferried to the town dock for a walk along the historical streets, viewing the Capital Building and other architectural masterpieces. Your Captain can help arrange an organized tour, or you can just wander around the shops, bars, restaurants in the colonial neighborhood near the water.  ​

Annapolis offers a nearly endless list of fine dining options, some of our Captains’ favorites include steamed shrimp at Davis’ Pub, a ribeye at Lewnes’ Steakhouse, or raw oysters and a crab cake at the Boatyard Grill. Watch the sunset from the shore or from Shardana’s deck, sipping on a beverage of your choice. It is, of course, your decision and part of the “Sail Your Story” mantra that drives the service of our Captains and crew.

“One of the things I love most about Captaining Shardana is giving clients their first exposure to sailing and watching as they take on more and more of the responsibilities of running the boat. Their knowledge grows, and their confidence soars.” –Captain Davis




Magothy River

39-03’22” N, -076-26’04” W

Early the next morning, Shardana will gently slip away from the Severn River/Annapolis harbor mooring field, and as we enter the main part of the Chesapeake Bay, sails again will be hoisted as we now sail north under the traffic jam on Route 50/301, aka– the famous Chesapeake Bay Bridge.

Depending on the prevailing winds, Shardana will sail on a broad reach–a point of sail considered by most sailors to be the perfect point of sail–to the Magothy River. We’ll set the anchor for lunch, a swim, or perhaps a short paddle board (we have two onboard).  After lunch, we’ll head northeast back to Rock Hall, and as the sun sets in the western sky, we’ll arrive back at Osprey Point Marina. The crew will secure Sharada to her slip, assist you in debarking, and your life will never be the same again.



Osprey Point Marina
Osprey Point Marina

Sailing on S/V Shardana is one of Maryland’s best Road Trips (“Sail Your Road”), even though we never have to touch the shore or use a conventional road. Enjoy a Maryland “Sail Your Story” road trip of an entirely different style.

To book your trip, visit:

About the Author

Thad Kubis is a U.S.C.G. licensed Captain, with a sailing and towing endorsement for Shardana Sailing Charters, Thad is also the marketing director for the firm. Thad is a certified Chesapeake Bay Storyteller, a professional photographer, an ASA Sailing Instructor, and has over 25 years of integrated marketing experience in the Travel and Leisure space.

Thad can be reached at 917.597.1891 or

Maryland Road Trips is a part of Postern Publishing.
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