Hi TCOG,
The way I understand your question, it seems that a WordPress “Custom Post Type” may be the ideal way to get this done.
Some theme developers have created themes which allow you to utilize a custom post type and display content the way you’re describing.
However, you could also use a plugin like Custom Post Type UI to accomplish this.
I don’t have experience with that particular plugin, but there are others. A quick search of the plugin repository using the phrase “custom post type” pulled up quite a few.
Essentially the idea is this: you create a custom post type called “wines.”
Each wine then becomes a “post” (of that custom post type). You could use the “featured image” to output a primary image for each wine. The “title” field would be for the name of the wine.
You could then use taxonomies to handle classifications (much like we use tags and categories for WordPress posts now) such as “type” (i.e. I’m thinking cabernet, merlot, chardonnay, reisling) or maybe “vineyard” or “vintage” and so on.
You could then create a couple of page templates to handle output of the content: one for lists of wines (like a simple version of the WordPress loop that only queries your new custom post type and outputs them styled the way you want), and perhaps one for a single post (a detail page for a given wine). You could potentially modify your theme’s “archive” template to show archives for your custom taxonomies.
This is a real quick and dirty attempt to describe the approach. You’ll probably run into some additional questions along the way. Custom post types are pretty killer once you start dabbling with them though.
Cheers!
