Shardana Sailing Charters
20 Minutes From Chestertown, MD
Private Sailing Charters Near Chestertown, Maryland
Looking for a sailing charter near Chestertown, MD? Shardana Sailing Charters welcomes guests from Chestertown and all across Kent County for private, captained sailing trips on the Chesapeake Bay. We're based just down the road at Osprey Point Marina in Rock Hall — a quick and scenic 15-minute drive from downtown Chestertown — making us the closest full-service private charter experience for Chestertown residents and visitors alike.
Whether you're planning a special celebration, a corporate outing, a family reunion, or simply a relaxing day on the water, Shardana offers a fully customizable sailing experience for up to six guests aboard our private yacht.
Why Chestertown Guests Choose Shardana Sailing Charters
Chestertown's charming waterfront on the Chester River gives residents a deep appreciation for life on the water — and Shardana brings that same spirit to the open Chesapeake Bay. Just a short drive from historic Washington College, High Street, and the Chestertown marina district, our private charters give you:
A private, personalized yacht experience — never a large group tour boat
A dedicated professional captain assigned to your trip
Fully customizable itineraries — swim stops, coves, beaches, wineries, or classic Bay towns
Proximity and convenience — only about 12 miles / 15 minutes from downtown Chestertown to our marina in Rock Hall
Flexible trip lengths — half-day, full-day, sunset, and multi-day overnight charters
Charter Options for Chestertown Visitors
Half-Day Sailing Charters
Perfect for a Chestertown morning or afternoon outing. Starting at $450, our half-day charters are ideal for couples, small families, or friends wanting a taste of the Bay without committing to a full day. Learn more about Half-Day Charters
Full-Day Sailing Charters
For Chestertown guests who want the complete Chesapeake Bay experience — cruising, swimming, and exploring nearby destinations like Rock Hall, Annapolis, or St. Michaels. Learn more about Full-Day Charters
Sunset Sailing Charters
A short drive from Chestertown delivers one of the most romantic evenings on the Eastern Shore — watch the sun set over the Bay aboard your own private sailboat. Learn more about Sunset Charters
Multi-Day & Overnight Charters
Turn your Chestertown getaway into a full Chesapeake Bay adventure with an overnight or weekend sailing charter, visiting multiple destinations along the Bay.
Getting to Shardana Sailing Charters from Chestertown
We depart from Osprey Point Marina, 20786 Rock Hall Avenue, Rock Hall, MD 21661 — an easy, scenic drive from Chestertown via Route 20 or Route 445, taking you through the heart of Kent County's waterfront countryside. Most Chestertown guests reach us in under 20 minutes.
We also welcome guests traveling from Baltimore, Washington D.C., Annapolis, Philadelphia, and Delaware, so Chestertown makes an ideal, low-traffic home base for your Chesapeake Bay sailing getaway.
Ready to Set Sail from Near Chestertown?
Your private Chesapeake Bay adventure is closer than you think. Contact Shardana Sailing Charters today to design a custom sailing trip that fits your Chestertown itinerary.