Chesapeake Bay Yacht Charters

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For Those Looking for a Private Yacht Experience on the Chesapeake Bay -- Baltimore, Annapolis, Kent Island and the Eastern Shore -- Pintail Yachts is no Longer in Operation As Watermark Continues Its Fourth Decade of Serving the Chesapeake Bay Region


Have you been considering chartering a yacht on the Eastern Shore for an upcoming event, anniversary or wedding reception? Then you may have discovered Pintail Yachts' vessels like Lady Pintail II and Duchess of Pintail at the River Plantation on Kent Island, Maryland. Pintail Yachts at River Run Plantation has been undergoing ownership changes and is no longer in full operation. We at Yacht Charters on the Bay by Watermark are often contacted by people looking for a similar experience as to what Pintail Yachts used to offer. We are happy to serve the Eastern Shore of Maryland and Kent Island with full service yacht charters for Eastern Shore weddings, family events, corporate events and special occasions.

Your private yacht charter can depart from various ports including the Eastern Shore, Annapolis or Baltimore. Our event planners specialize in elegant, fun and memorable events. We’re happy to assist with event planning, securing vendors and always provide event day coordination. Yachts are a great – and very unique – option when seeking outdoor wedding venues in Maryland. They offer the best of many worlds -- an elegant indoor venue, an outdoor venue, an ever changing backdrop, waterfront views – and are a refreshing choice when looking for perfect Eastern Shore wedding venues and wedding venues in Maryland.

Similar to Pintail Yachts’ Maryland charter boats, our fleet of vessels means we offer a variety of Eastern Shore wedding venues. Let Watermark serve your private charter needs!

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