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 is a unique, private Chesapeake Bay sailing adventure for up to six passengers. Each journey promises a special and personalized cruise that will elevate your life beyond the ordinary. Each of our sailing charters is custom arranged for you. Your experience begins the moment you contact us. We are customer-focused and work with you to custom design a fun sailing adventure just for you and your party. Whether you want a day trip, sunset sail or multi-day sailing trip, we link your leisure time off and desires to our experience and expertise.
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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