Meet the Crew Behind Chesapeake Windsail Cruises
Captains
Meet the experienced captains guiding your journey on the Chesapeake Bay.
Derek
He has spent the past 30 years immersed in the boating community on the Chesapeake Bay. An avid waterman, he enjoys being on anything that floats—whether it’s a kayak, powerboat, or sailboat. With over two decades of sailing experience, Derek has a strong background in both cruising and racing on the Bay, and he regularly charters in the Caribbean. Derek enjoys introducing people to and promoting the natural beauty and cultural heritage of the Chesapeake Bay.
Steve
He grew up on the West Coast near Seattle, Washington, where he developed a love for the waterways of the Pacific Northwest — from waterskiing on local lakes to deep-sea fishing off the coast. He retired from the Coast Guard Reserve, including a tour aboard an icebreaker sailing around Antarctica. For the past 10 years, Steve has been sailing on the Chesapeake Bay, participating in Wednesday night races out of Herrington Harbor and cruising up and down the bay aboard his own 30’ and 47’ sailboats. He also enjoys bareboat sailing throughout the Caribbean and Mediterranean.
Bob
He has had a passion for sailing for many years. The Chesapeake Bay has long been his playground—whether exploring its quaint harbor towns, racing across its broad waters, or enjoying its dynamic marine life. He has also enjoyed sailing with family throughout the Caribbean, Croatia, and other parts of Europe. Bob takes particular pleasure in sharing the beauty of sailing with others and is a sailing instructor on the Potomac River in Washington, D.C. His other passion is music. Bob plays the double bass with the National Symphony Orchestra (NSO), based in Washington, D.C.
First Mates
The friendly faces behind every great day on the Chesapeake Bay.
Jennifer
She loves sailing and boats. Since 2024, she has logged well over 3,000 nautical miles under sail, including voyages along the entire East Coast of the United States, as well as to the Bahamas and throughout the Caribbean. Jennifer experience includes extensive sailing on the West River, throughout the Chesapeake Bay, and offshore passages. For her, any day on the water is better than time spent inside!
Nate
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!
Kevin
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 Island, 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!