Day Trips from Philadelphia
Looking for a day sailing trip close to and easily accessible from the Philadelphia area? Shardana Sailing Charters welcomes guests from the Philadelphia area for private, captained sailing trips on the Chesapeake Bay. We're based less than 2 hours away from Philadelphia at Osprey Point Marina in Rock Hall, Maryland—making us the closest full-service private sailing charter experience that offers a true nature escape for Philadelphia area residents
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.
Shardana Sailing Charters
Only 1.5 hours from Philadelphia
Why Philadelphia Area Residents Choose Shardana Sailing Charters
Shardana Sailing charters creates a mini-vacation or quick getaway to the open Chesapeake Bay. No noise, no crowds—just a true escape a short drive from historic Philadelphia.
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, restaurants, and 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 Visitors from Philadelphia
Half-Day Sailing Charters
Perfect for a 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 Philadelphia day trippers 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
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 Philadelphia 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 the Philadelphia Area
We depart from Osprey Point Marina, 20786 Rock Hall Avenue, Rock Hall, MD 21661 — an easy, scenic drive from Philadelphia via I-95, the on to Route 1 over the scenic Chesapeake and Delaware Canal then on to Route 301 taking you through Delaware and then through the heart of rural Kent County.
We also welcome guests traveling from Baltimore, Washington D.C., Annapolis, Philadelphia, and Delaware.
Ready to Set Sail from Near Philadelphia?
Your private Chesapeake Bay adventure is closer than you think. Contact Shardana Sailing Charters today to design a custom sailing trip that fits your itinerary.