PRIVATE CHESAPEAKE BAY SAILING TRIPS
SHARDANA SAILING CHARTERS
Half Day Sailing Trips
Full Day Sailing Trips
Sunset Sailing Trips
Mutli-Day Sailing Charters
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Sailing Chesapeake Bay
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Shardana Sailing Charters offers private captained sailing charters on the Chesapeake Bay from Rock Hall, Maryland. Shardana offers an exceptional range of sailing charters designed for every kind of adventurer. From relaxing half day excursions and full day sailing charters to breathtaking sunset sail cruises and immersive weekend sailing getaways, each charter is thoughtfully crafted to showcase the beauty of sailing the Chesapeake Bay. Fees are for the entire boat (not per person) and start at $450 for half day charters. All charters have a maximum capacity of six passengers.
We specialize exclusively in private sailing trips and charters, ensuring a personalized and intimate experience for every guest. We are located at Osprey Point Marina in Rock Hall, Maryland. Every voyage with Shardana is fully customizable — from the route and activities to the pace of your day — allowing you to create the perfect itinerary that matches your vision, whether it’s a romantic escape, a family outing, or an adventure with friends. Visit classic destinations like Annapolis and Saint Michaels, anchor for a swim and explore a secluded cove, hike a beach or visit a winery. While most of our guests come from Maryland, Baltimore, Washington DC, Annapolis, Philadelphia, and Delaware, we have welcomed families and groups from New Jersey, Pennsylvania and all over the USA. Our sailing charters provide the most authentic and classic Chesapeake Bay experience . Don’t just take our word for it. Check out some of our customer reviews here.
Shardana Sailing on Chesapeake Bay
Shardana Sailing Charters offers private, captained sailing charters on the Chesapeake Bay from Rock Hall, Maryland. Enjoy a relaxing and personalized sailing experience aboard our 42-foot yacht with your family, friends, or someone special. Choose a 3-hour sail, sunset sail, full-day charter, or multi-day sailing adventure. Explore the Chesapeake, enjoy the scenery and wildlife, celebrate a special occasion, or simply escape for a few hours on the water. Our private charters are ideal for couples, families, groups, and visitors looking for a memorable Chesapeake Bay experience.
Private Captained Sailing Charters
It all starts with you, our guests. When you take one of our sailing charters, we assign you your own personal captain. Your captain will assist you in planning your charter the way you want it, based on the type of charter you choose. Owners Andrew and Davis carefully select each Captain. They choose each captain for their superb professional maritime skills, experience, and their interpersonal skills.
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