I have a done a bit of sailing in my life. I've sailed extensively in the Mediterranean, including Greece, Italy, Turkey, and the former Yugoslavia. I've also sailed the Caribbean, including the British Virgin Islands, US Virgin Islands, Puerto Rico, Dominican Republic, Jamaica, Grand Cayman, Bay Islands of Honduras, Belize, Granada, St. Lucia, and the San Blas Islands of Panama.
I recently discovered a new phenomenon (to me), sailing vlogs on YouTube. A number of people (primarily couples) have started posting their sailing adventures online. Most of them are members of Patreon which allows some of their ardent viewers to contribute money to their ventures.
Each vlog represents the particular sailors. Different type of boats, different personalities, and different lifestyles provide a wide ranging view experience.
You can locate most of these vlogs by searching their name on YouTube
Here's a partial list:
S/V Delos
Sailing La Vagabonde
Ran Sailing
MJ Sailing
Sailing Doodles