The town of Los Olivos is a one-stop shop for wine country cuteness. It's packed with tasting rooms (special shoutout to Dreamcôte; Stolpman and Carhartt are fun, too; there's truly no shortage of good options), little shops, and relaxing vibes. Once you pull into town, ditch your car and stroll around; you can walk everywhere within minutes. For restaurants, we've loved Nella Kitchen and Los Olivos Wine Merchant & Cafe (the latter is more casual lunch). Bar Le Côte is all the rage and we're dying to go. Check out Lefty's Coffee for caffeine and a nice backyard.
"The Danish Capital of America" -- founded by three Danish immigrants in the early 20th century, this town has a ton of kitschy character. It's all walkable; stroll around and dip into a tasting room, grab a pastry at one of the million bakeries, have lunch or dinner at Peasant's Feast or the Landsby, and (if you're into it) check out the free Hans Christian Andersen museum.
This place is VERY California. And by that, we mean it is entirely outside (save for a greenhouse, which is open-air and thus basically outside), it has a relaxed-chic vibe, and it serves delicious natural wines (and funky beers). You could hang here all day. Sometimes there are pop-up food carts in the back. The bathroom has fun wallpaper. There is a bocce court!
When in Los Olivos, taste some olive oil, for god's sake! No reservations required. While you're here, roam around the tranquil property, play a game of corn hole, check out the gift shop, and maybe buy a bundle of lavender for the road.