Our Story

A young child in a yellow life jacket on a boat with an American flag.

Chesapeake Classic Yacht Charters was born from a passion for the water and a love for the rich maritime history of Annapolis. Our journey began with our own nostalgic experience of growing up on these vibrant waters and a vision to share our own experience with others. With the only Hinckley Picnic Boat available for charter in the Annapolis area, we offer a sophisticated way to experience the Chesapeake Bay’s historic waterways in style and comfort. Our mission is to tailor every charter to the desires of our guests and to provide a safe and memorable experience, whether it's a romantic sunset cruise, a corporate outing or a relaxing family day on the bay. We invite you to be a part of our story and discover why Chesapeake Classic Yacht Charters is the preferred choice for those seeking a sophisticated experience on the water.

Four young children wearing life jackets sitting on a boat with an American flag; boats and water are visible in the background.

Our Captain

A man standing on a small yacht with a U.S. flag, near a marina with boats and buildings in the background.

Captain Donald Patterson grew up with a love for the water and a passion for boating.  Originally from Maryland, Donald grew up in Virginia Beach, VA and spent summers with his family in Annapolis learning to sail on the Chesapeake Bay.  He enjoys offshore sailing and has completed several of the renowned Annapolis to Newport and Newport to Bermuda regattas.  He also enjoys power boating and exploring the Chesapeake Bay with his wife, 4 young sons, and golden retriever aboard his Hinckley Picnic Boat, Proud Mary. 

Our Yacht

A boat named 'Proud Mary' from Kilmarnock, VA, with an American flag, sailing on a river with a church and trees in the background.

Proud Mary is a 2000 36’ Hinckley Picnic Boat, handcrafted by the Hinckley Company in Southwest Harbor, Maine.  The classic lines, polished teak, state-of-the-art jet drive system, and comfortable design make the picnic boat a luxurious choice for cruising. The name Proud Mary honors the name of the Navy Swift Boat which Donald’s father navigated as a young sailor during the Vietnam War.  The hailing port of Kilmarnock, VA pays tribute to Donald’s late father’s weekend retreat on the Chesapeake Bay.

Our Town

Lighthouse on stilts over water with a red roof, surrounded by ocean, rocks at the base, and a sailboat in the distance under a blue sky.

Discover the rich maritime history and stunning shorelines of Annapolis and the Chesapeake Bay by water with us aboard Proud Mary! Established in 1649, Annapolis is the crown jewel of the Chesapeake Bay.  Discover the quaint historic downtown waterfront from Ego Alley and view the United States Naval Academy from the water.  A cruise up the bay will showcase the famous Chesapeake Bay Bridges, which connect Annapolis to Kent Island and the Eastern Shore of Maryland.  Cruising south from Annapolis will feature the iconic Thomas Point Shoal Lighthouse, one of the last remaining screwpile-style lighthouses on the Chesapeake Bay.  After your charter, stop by one of our local favorite restaurants for lunch, dinner, or a cocktail! Check out our blog for our favorite day trips and our social stories for our favorite local spots!