Servicing Annapolis Maryland and the greater Chesapeake Bay waterfront area.
Bringing performance and recreational sailboats, equipment, apparel, and repairs to Annapolis and the greater Chesapeake Bay!
As a veteran-owned and operated small business, we strive to serve the local sailors and performance water sports athletes of the Chesapeake Bay with the best boats, equipment, repairs, and expertise to make competitive sailing and other watersports accessible and sustainable for all.
A veteran-owned and operated company, Jake Crespin and Jeff Daigle established Annapolis Sail Works in 2023 to serve the Chesapeake Bay waterfront community with high-quality sailboats, equipment, repair services, and expertise. Jake and Jeff are both avid lifelong sailors with extensive sailing and marine industry backgrounds and a passion for boats, performance, and recreational sailing. Jeff is a retired career Coast Guard Helicopter Pilot and a Texas Maritime Academy graduate, where he was captain of the varsity sailing team. Jake is a career Marine Corps Infantry Officer and graduate of the U.S. Merchant Marine Academy, where he sailed on the Kings Point varsity dinghy and offshore teams. Both owners race various classes of dinghies, keelboats, and offshore boats. They founded Annapolis Sail Works to make high-performance and recreational sailing on the Chesapeake Bay more accessible and sustainable by bringing a full-service dinghy shop back to Annapolis, MD.