PISMO BEACH

An iconic surf destination with great breaks at high tide, warm waters, and a solid swell direction that's ideal for all skill levels, Pismo Beach is one of California's premier surf spots. Even if you're not hitting the waves yourself, the 17 miles of shoreline and sun-dappled cliffs are enough to make you consider diving into the water—or at least a move to SLO. Enjoy a romantic stroll on that picture-perfect pier, where you can usually spot the surfers bobbing around and under it between rides.

Edna Valley and Arroyo Grande

Nearby Paso Robles may get all the attention, but San Luis Obispo is home to not one but two excellent wine regions of its own. Edna Valley and Arroyo Grande produce more than 40 grape varieties, thanks to that crisp marine air, the rolling hills and shaded valleys, and the year-round Mediterranean climate. The scenery is worth the drive alone, but you'll be rewarded with stops at wineries like Talley Vineyards, home to live music, picnic lunches, berry picking, and some of the region's best chardonnay and pinot noir. There is also Laetitia Vineyard & Winery, which hosts grape-stomping parties, a wine club, and live bands.

Madonna Inn

One of the world's kitschiest hotels is also one of San Luis Obispo's most colorful landmarks; welcome to the pink-and-white Madonna Inn, where over 100 uniquely themed rooms await. Standouts include the hunting lodge, gold glitter, Old Mexico, and the magnificent Jungle Rock, decked out in faux tree branches and vines. The grounds and activities include a scenic pool, trail rides, live theatre, and a hot-pink tennis court. If you're just stopping by (more fool you), you should visit the all-pink steakhouse, the copper-accented café and bakery, and the rose-tinted Silver Bar for a bite and a drink. Yes, it is kitschy, but what else do you expect? Embrace it.