If you want to charter an Island Packet you can try Gratitude Yacht Center which is located here on the Chesapeake. Sailboat Charters Rock Hall Maryland | Bareboat Sailboat Charters Chesapeake Bay | Gratitude Yachting Center Rock Hall MD
Smaller independent charter companies will often have IP as well as a broad spectrum of other boats in their fleets, I don't have time to respond to your other questions.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay and part-time purveyor of marine supplies