Tall Ship Chronicles was a television series produced in Canada in 2001 and 2002. It followed the training of Canadian journalist and actor Andrew Younghusband on an 18-month sail training voyage around the World, on the barque Picton Castle.  The show follows the interpersonal relations between many of the people on board while also showing a bit about the various islands the ship visits during the voyage. 

 
https://en.wikipedia.org/wiki/Tall_Ship_Chronicles

Originally ripped from VHS tapes