Living in New York has its advantage that pretty much any wine store will have at least a few bottles of kosher wine. At least the basics of a red, white, various degrees of dry to sweet. Outside of major Jewish areas, often the options quickly dwindle to kosher grape juice and if one is lucky, the very sickly sweet traditional wine.
So when I began my journey out of state, this is where KosherWine.com was a lifesaver for two reasons, the huge selection and the price. Check out the free shipping area for case selection that ship free if you are looking to stock up.
A few years back our shul give a wine of the month subscription to our rabbi, who was a wine enthusiast and he greatly enjoyed.
Like many of my posts, there is an affiliate link, clicking through my site costs you nothing but I earn a tiny cut. Not much but helps me with this blogging hobby.