Meet the Crew

Schooner Woodwind Captains


 Captain Jen, Schooner Woodwind CaptainJennifer

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.


Captain Ken, Schooner Woodwind CaptainKen

Ken followed his passion and taught instrumental music for 25 years in Connecticut. When budget cuts ended the program he and his family commissioned to have Woodwind built and started the business 20 years ago. Ken considers himself very lucky indeed to follow 2 dreams. One about music the other about sailing.


Captain Mike - Schooner Woodwind CaptainMichael

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 bareboat charter company in Annapolis. Mike enjoys sharing his interest in ecology and maritime culture.


Schooner Woodwind Captain MickeyMickey

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/sailed in the Caribbean for 24 years, I returned to the Bay in 2008 and enjoy every day I am on the water!!


Schooner Woodwind Crew


AndyAndy B

Andy learned to sail in a small day sailer on a lake in Pennsylvania. Eventually the lure of larger boats and better cruising grounds led him to discover Annapolis. After 25 years in a traditional desk job, a change was in order! He is now a certified sailing instructor and crews for us on Woodwind.



I’m a college student with a summer job on the Woodwind, from Pittsburgh PA. I love to sail, cheer for the Steelers, meet new people, and read. This is my second year working on the Woodwind.



I am the youngest crew mate out of everyone at the age of 19 years old. I have recently finished my freshman year of college, with a major in biology, at Virginia Tech. I have 4 years of competitive sailing experience that I learned through my time on the sailing team at Severna Park High School. Most of my sailing experience was learned on smaller sailing vessels such as a 420 and FJ.


Native Annapolitan and set it and forget it gonk holing cruiser, except aboard the Woodwind.




I am 26 years old and I love being on the water.




By early morn a seamstress, by night a sailing siren, I’m just a simple Annapolitan girl who likes having a good time with some wind in her sails. I’ve been sailing for 3 years, including a Regatta in Grenada and several other sails through the Caribbean. I love being out on the open waves.


Schooner Woodwind Sales & Support Staff


 BethBeth, Schooner Woodwind Sales Manager

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.


 Whit, Schooner Woodwind DockmasterWhit

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.


I was born in Annapolis and raised in the surrounding area. The Chesapeake and her tributaries have entertained me as well as inspired delight throughout my life. I moved away once for 2 years, and could not wait to get back to the waters that fill and support my spirit! I love sharing my joy with others! Come see me at the Customer Service window on the dock by the Woodwind!


Kate works in the office handling group and private charter sales for the company. Originally from New England, she moved to Annapolis last summer to join the Woodwind team and is so happy she did! She has quickly come to love sailing. As a former wedding florist, she enjoys sales tremendously and loves working with clients to plan fantastic events and cruises aboard the Woodwinds.


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