Meet the Crew


Captain Andy served 39 years with the military, police and federal law enforcement with multiple overseas assignments. His sailing resume reflects ASA instructor ratings, and extensive sailing experience in the Caribbean, Mediterranean and Pacific oceans including Greece, Croatia, France, Belize and Tahiti. Captain Andy is fully committed to the continued restoration of the Chesapeake Bay and its wild life.


Captain Floyd grew up on the Bay and has been on and around boats all his life. He has over 9000 miles of offshore experience mostly in the South China Sea. He and his wife Donna lived aboard their 42ft ketch in Hong Kong for 11 years while cruising and experiencing Thailand, Vietnam, Malaysia, Indonesia, Singapore and the Philippines. Returning to the US and the Chesapeake a few years ago he loves being able to share his love of sailing and introducing new people to the joys of being out on the water.


Captain Jayne has been sailing since she was a kid in Australia, in dinghies on Port Phillip Bay and then further afield in larger sailboats with her family. She now races and cruises her own boat and crews for a larger boat in offshore races. When not racing, Jayne teaches a sailing program for women, moves sailboats and powerboats up and down the east coast and in the Caribbean. She is a qualified lawyer and has worked in trademark and brand protection for nearly 30 years.


A former U.S. Naval Officer, teaches Midshipmen at the U.S. Academy to sail 44 ft sailboats during summer training. He loves sailing on the Chesapeake Bay.


His love of the Chesapeake Bay and sailing has existed for more than 40 years. He cannot decide which he loves more… the grandkids or sailing. His solution is sailing with the grandkids!


His love of the water started with his first job as a mate on charter fishing boats as a teenager and later after high school he became a commercial clammer on Long Inland, New York. He is a retired meteorologist, has been sailing since his twenties, and has owned several sailboats. But he still loves to be on the water to catch the wind!


Andres picked up sailing, in his teenage years, but it wasn't until COVID-19 hit that he started doing it frequently. From overnight trips to offshore adventures, he embraced many aspects of sailing. The Chesapeake Bay holds a special place in his heart for its beauty and challenges, offering endless opportunities for exploration.


Tom grew up sailing small boats on the Potomac River and its tributaries. He spent a few years away from the water and has recently caught the bug to sail on larger boats and enjoy the freedom that sailing on the Chesapeake Bay provides. He enjoys summer days on the water, followed by eating steamed crabs.


Stephanie fell in love with sailing and the water growing up on the Great Lakes and the Indiana Dunes. She sailed with her grandfather and uncles on Lake Erie as a child. When Stephanie is not sailing she enjoys hiking and traveling.


Scott has sailed on the Chesapeake Bay and the Penobscot Bay, Maine for over 40 years. He also loved the experience of working on lobster boats for a few summers in Maine. Scott was raised in Maryland, and has lived with his wife in the Twin Beaches area for the past 25 years. He has a deep love and appreciation for the local history and the waters of the Bay.


She is a rising senior, who loves spending time outdoors in her community. She has grown up in Chesapeake Beach and North Beach her entire life, therefore, becoming acquainted with the history that surrounds it. She enjoys interacting with others and hopes to supply people with new information and enjoyment.


Washington, D.C. born and Maryland native, Jana has been happily living and raising her family in the Twin Beaches for 20 years. She wouldn't live anywhere else and is proud to show visitors many of the highlights here at her favorite spot in the world.


Scott A Maryland native, Scott has enjoyed living with his family in the Twin Beaches area for the past 25 years. Recently retired from the U.S. government where he worked as a historian and Museum Administrator, Scott is thrilled to now have more time to research local Maryland history, create digital art, and frequent the many fascinating and fun places of interest this great community has to offer. He would greatly enjoy sharing these interesting places with you.

Chesapeake Windsail Cruises