Sailing Doodlesvideo

An Emotional Goodbye to Taylor - S5:E72

22 October 2020 · 11 min · 706K views · Annapolis

What this video covers

Bobby and Taylor conclude their sailing season aboard their 1989 CT56, Doodles, by completing a 20-mile passage from St. Michael’s to Annapolis, Maryland.1:19 During the transit, the crew grounds the vessel in soft mud while exiting port, noting that the Chesapeake Bay’s bottom composition typically prevents hull damage during such incidents.2:20 Upon arrival, they secure a slip at Chesapeake Harbour Marina, which they describe as a well-protected facility featuring a beach, showers, and an on-site restaurant.5:00 The crew spends their final evening together dining at the Annapolis Yacht Club before Taylor departs for Canada.6:50 Bobby plans to perform boat upgrades during the off-season before resuming cruising.1:10

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Boats in this video

Island SPIRIT 525Their boatTa Chaio Shipbuilding Co. (TAIWAN) Ct-56Their boat

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