Antique and Classic Boats for Sale in Chesapeake Bay

Antique and Classic boats in Chesapeake Bay, MD offer a unique opportunity to own a piece of maritime history while enjoying the vibrant waters near Annapolis. Whether you’re seeking meticulously restored classics or well-maintained used vessels, our listings cover a range of options perfect for sailing, cruising, or weekend getaways. Act quickly—these popular boats sell fast during peak season, especially with the boating culture thriving in this region. If you don’t find your ideal antique or classic boat in Chesapeake Bay, consider nearby cities like Baltimore or Norfolk for additional listings.