Meet the Crew

Schooner Woodwind Captains


Captain Jen, Schooner Woodwind Captain 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.


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!!



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.


Schooner Woodwind Crew


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



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.


Started boating in Ohio with 16′ Starcraft, lots of fishing and skiing on Miami River and Lake Erie.  Began sailing in the Bahamas?  Met folks there from and Annapolis and started Racing keel boats on the Chesapeake.  Achieved my USCG Masters license in 1985 and worked charters, schools and deliveries for about 19 years. Covered waters from S’West Harbor Maine to USVI.

pat Pat

A Pasadena native Patrick grew up sailing on the Chesapeake bay with family. After graduating from college in 2013, Pat crewed on the Pride of Baltimore II as well as the Privateer Lynx. Patrick contends he is a hero in his mother’s eyes.


Schooner Woodwind Sales & Support Staff

Beth, Schooner Woodwind Sales ManagerBeth

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 Dockmaster 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.



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!



Originally from Hoboken NJ, I started out as an OB/GYN nurse then switched to my passion of setting up special events working for the Macy*s Parade & Special Events n NYC and freelance event planning, I know I can “Deliver” a memorable event for your group or private charter. My motto: Life is better with a tiara!



I am a life long sailor. I grew up as a “boat Kid” terrorizing the back waters of Lake Erie from my first motorized vehicle, an inflatable boat with an outboard. I grew up (so to speak) to become a professional boat captain and moved to Annapolis where I lived aboard my own 33 foot sailboat.  As an event sales associate for Schooner Woodwind, I get to share with our clients, my love for the sea.


© Copyright 2015. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.