Meet the Schooner Woodwind Captains
Jennifer
Sailing has been a vital part of Jen’s life since she was 5. Racing and cruising with her family filled her summers until she started teaching kids to sail. Her sophomore year in college, she sailed on a 125-ft schooner for credit in science, literature, and history. She now was addicted to schooner sailing. 3 years later, her family built the Woodwind. At 26, she became a captain.
Ken
What do I want to do when I grow up? For me, it was, ask the question what do I love to do that I can share with others and make it a career? I taught instrumental music to elementary students for 25 years. When that was no longer an option due to budget cuts, I asked the question again? This time the answer was, with the help of my family, Schooner Woodwind.
Michael
Captain Mike is a Chesapeake native and a resident of South Baltimore. He joined the Woodwind in 2010, after running traditional Chesapeake work boats focused on outdoor experiential education. Mike has managed sailboat fleets for a sailing center in Baltimore and a charter company in Annapolis. Mike enjoys sharing his interest in ecology and maritime culture.
Mickey
Working as a Captain on the Schooner Woodwind is awesome. I figured out how to get paid for my favorite hobby(sailing). I started sailing when I was 6 years old right here on the bay. I am a very avid sailboat racer and when not working you can usually find me out racing. I lived in the Caribbean for 24 years, I returned to the Bay in 2008 and enjoy every day I am on the water!!
Meet the Schooner Woodwind Crew
Don
I’ve been sailing since the age of 12. During 20 years in the Navy, I sailed while visiting ports and while at home. I am a personal coach using horses in my work. I’ve owned a C&C 30, a Catalina 400 and 470 and sailed Hobie 16’s in Aruba, and a 110’ schooner in Fiji, and a CT44 from Bermuda. I am a published author, write music, dive, and like birding. I sail whenever I can.
Glenn
Just a simple guy that loves spending time on the water with great people.
Rena
Rena is a native Baltimorean who fell in love with sailing 6 years ago. A former hairstylist, she dreamed up her career in the marine industry when she was “stranded” in St. Thomas during Snowmageddon. 2012 will be her 3rd season on Woodwinds. She hopes to some day be a liveaboard and travel to distant shores.
Nathan
I am a recent arrival to Annapolis and a graduate of St. Mary’s College of Maryland. I enjoy sailing, cooking, gardening, playing piano, windsurfing, kayaking, and writing. There are usually a few worn out water damaged books in my bag at any given time.
Meet the Schooner Woodwind Sales & Support Staff
Gretchen
Gretchen started sailing in middle school with her step-father who used a Texaco road map to navigate so she is very happy to sail with the skilled captains and crew of the Woodwinds! Gretchen has worked in event planning since graduating from college and enjoys helping people plan fun events that have them out sailing on the Bay!
Beth
Beth is a natural born sales person. Her attention to detail serves her well in organizing private cruises and group events aboard Woodwind. Though she has not always been a sailor by nature, after several years sailing aboard the Schooner Woodwind she enjoys sitting back and enjoying a relaxing sail while Woodwind’s crew takes care of everything else.
Deanna
As a kid, being near the water was a way of life for Deanna. She learned a love of sailing from her dad while living in the Seattle. With a BA in Business and HR background, she found the best of both worlds by combining her professional life with an activity she loves. Being involved in behind-the-scenes work and selling a joy of sailing since 2005 has been fun.
Whit
Every morning I walk out onto the dock overlooking the Annapolis Harbor and wonder who I might meet or what I might see or experience that will make this day a great day. I love working outside, we have the best office and views in Annapolis. The Woodwind Family all works hard because we love what we do and most importantly we have a good time doing it.









