Boat Charters

A charter boat cruise with a professional yacht captain is the ideal way to explore, experience new destinations and get out on the water.

Explore our how-to and best practice articles from our Featured Contributor, by charter category and the latest articles on boat charters.

Captained Charters

How to hire a charter & what to expect

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Flotilla Cruises

Multi boat & captain cruising

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Overseas Charters

Cruising or chartering a boat overseas

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Follow Capt. Rob


CAPT. ROB CHICHESTER is an engineer and owner & operator of Chesapeake Flotillas offering charters, instruction, and vessel relocation. A USCG Licensed Master, Capt. Rob has planned and executed flotilla cruises all over the Chesapeake Bay, Europe, and the Caribbean. Rob holds a 200-Ton Master's license with Auxiliary Sail and Assistance Towing endorsements. He also is certified by the American Sailing Association to teach Basic Keelboat Sailing, Basic Coastal Cruising, and Bareboat Chartering. A self-proclaimed sailor & poet, he operates a 41-foot sloop Bay Poet based out of Rock Hall, MD.