I'll definitely second the recommendation of Keep Turning Left by Dylan Winter who started nine (!) years ago to circumnavigate the UK one creek at a time while filming and narrating his voyage in a shoal draft
19-footer lovingly called "The Slug". He since has changed boats several times (all small craft, with a personality as interesting as his) and he's still at it. His commentary includes historical tidbits and lots of other observations (great shots of birds and other wildlife as well). The videos can be bought (very cheaply) on DVD
from his web site but are also available for free and in better quality than on Youtube here:
A much newer vlog in a somewhat different vein that I haven't seen mentioned so far is "Winded Voyage":
Swiss lake sailor Alex (with an American background, the vids are narrated in English) decides to buy a 40-ft Jeanneau
in the South of France
and gets ready to sail the world--but first he persists in getting his Swiss Ocean Master (not sure about the exact name) license
which besides a lot of theoretical cramming requires 1,000 miles of documented ocean sailing! Finding the boat and getting the license
are the topics of the first season and he's just started the second season now, venturing out on his own. The videos are concise and well edited. For me, they have the added attraction that I am intending to buy a boat in the same general area that he did.
Both of the above recommendations are "bloke" videos fairly short on bikinied first mates. For those, I of course love SV Delos, La Vagabonde, White Spot Pirates, Rick Moore etc. etc.