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CAPCA Board Member at Large
Captain Rob Doolittle
USCG 25 Ton Master w/ Sailing Endorsement
Rob began sailing as an adult, when he and Joanne, his wife, took a 3-hour dinghy sailing lesson in Nantucket while on vacation. Later Rob earned his US Sailing Small Boat Sailor certification on the Potomac River. After a friend told him that completing ASA 101-103-104 would allow him to charter boats in exotic locations, Rob set his sights on future cruises and began chartering the very next year. Since then, he has skippered outings in the BVI and New England, with cruises in Spain and Croatia on the near-term horizon. He and Joanne have owned a Beneteau 311 since 2015, which they keep in Annapolis.
Rob is an ASA 101/103 instructor with several Chesapeake ASA affiliates, as a well as an offshore-qualified skipper/instructor for the US Naval Academy’s Command and Seamanship Training Squadron (CSTS). Through the CSTS program Rob helps Midshipmen develop their leadership skills in the unfamiliar and physically challenging world of offshore sailing.
Rob has crewed offshore sailboat deliveries between Florida and North Carolina, up and down the Chesapeake and on northern portions of the ICW. As a racing-crew member Rob completed the 2024 Annapolis-to-Bermuda competition, an attempt at the 2023 Annapolis-to-Newport race (his boat withdrew due to equipment failure) and he crewed for several years in the Herrington Harbour Sailing Association’s Wednesday night racing series.
Previously Rob served as Fleet Captain for the Annapolis Naval Sailing Association. He also has many years of experience serving in volunteer roles with professional associations such as the National Press Club, the Association of American Railroads, AFCEA International, the Northern Virginia Technology Council and others.
Having earned his mariner credentials in early 2024, Rob is focused on captaining outings for clients of local charter companies and completing additional East Coast deliveries.