Spring is Here!

If you’re an Annapolitan, you know that with the arrival of spring comes the arrival of boating season! Here in Annapolis, we kicked off the start of the new season with the Annapolis Maritime Museum’s Annual Sock-Burning and Oyster Roast, an iconic community celebration of giving a symbolic farewell to the sock-wearing season for sailors and welcoming spring and boating season! As the temperatures continue to warm, we are busy here at Chesapeake Classic Yacht Charters preparing our Picnic Boat, Proud Mary, for the 2025 boating season! We are wrapping up a few final projects and are stocking up our signature Boat Tote with all of the essentials you’ll need to spend a lovely few hours on the water with us this year! Follow our social media for more updates, including a countdown until our website and 2025 booking go LIVE!

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Spring Special Event Charters

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“The Hinckley Way”: 100 Years of Elegance and Excellence