Private Sailing Charters Near St. Michaels, MD

St. Michaels is one of the most beloved sailing towns on the Chesapeake Bay — and it's also one of the classic destinations our guests visit aboard Shardana Sailing Charters. Based at Osprey Point Marina in Rock Hall, Maryland, we're located across the Bay from St. Michaels, offering St. Michaels-area visitors and residents a private, captained sailing charter experience that includes the option to sail right into town.

Whether you're staying in St. Michaels for the weekend or you call it home, Shardana can build a custom itinerary that starts at our Rock Hall marina and brings you into the heart of one of the Bay's most picturesque harbors.

• A private yacht for up to six guests — a personal alternative to St. Michaels' harbor tour boats

• A dedicated professional captain who tailors the sail to your interests

• St. Michaels as a featured destination on many of our multi-day itineraries

• A scenic sail or short drive from St. Michaels — approximately 30–35 miles / about an hour by road, or a beautiful sail across the Bay

• Fully customizable itineraries — coves, beaches, wineries, and other Eastern Shore towns

Why Visitors to St. Michaels Choose Shardana Sailing Charters

Charter Options for St. Michaels Guests

Half-Day Sailing Charters

A relaxed way to get out on the water without giving up a full day of your St. Michaels visit. Starting at $450. Learn more about Half-Day Charters

Full-Day Sailing Charters

Combine time in St. Michaels with a full day of sailing, swimming, and exploring nearby Bay destinations. Learn more about Full-Day Charters

Sunset Sailing Charters

Watch the sun set over the Chesapeake with a route that can include views of St. Michaels' historic harbor. Learn more about Sunset Charters

Multi-Day & Overnight Charters

Make St. Michaels one stop on a larger multi-day sailing adventure that also visits Rock Hall, Annapolis, and other classic Bay towns.

Getting to Shardana Sailing Charters from St. Michaels

We depart from Osprey Point Marina, 20786 Rock Hall Avenue, Rock Hall, MD 21661. From St. Michaels, the drive north along Maryland's Eastern Shore takes roughly an hour via Route 33 and Route 213. Many of our multi-day itineraries also sail directly between the two towns.

Get Directions to Osprey Point Marina

Ready to Set Sail from Near St. Michaels?

Experience the Bay the way it was meant to be sailed. Contact Shardana Sailing Charters today to design a custom trip that fits your St. Michaels visit.