San Luis Obispo, or SLO as the locals call it, has multiple personalities: meeting point between SF and LA, outdoorsy collegiate town, oenophile getaway perched 30 miles from Paso Robles. They all converge into an ideal and easy-to-do weekend for anyone who loves food, wine, mountains, and ocean—which is to say, most of us.

For convenience, base yourself at Petit Soleil, a B&B that's walkable to downtown and looks like a Motel 6 made over as a Provencal inn. Funky, friendly, and charming, it offers delicious breakfasts like baked eggs and chocolate-chip pancakes along with free wine tastings each afternoon.

However, save one breakfast for SLO's legendary Big Sky Cafe, an airy eatery brimming with regulars and visitors alike. The casual crowd—from surfers to hikers to families—is a good induction into SLO culture, and the red flannel turkey hash, beignets, and pozole will fuel you up for the day. First, wander the pretty downtown, ducking into Boo Boo Records for vinyl and a healthy dose of authentic record-store atmosphere as well as Finders Keepers Consignment for designer vintage.

Then hop in the car, and drive to Paso Robles for an afternoon of wine tasting. The region devotes more than 70 percent of its acreage to Cabernet, Merlot, Syrah, and Zinfandel, but with 175 wineries to choose from, look out for interesting Rhone varietals and blends as well. Make your first stop Denner Vineyards, whose gravity-flow system (no pumps) produces the usual reds, lovely Viogniers, and culty blends like Mother of Exiles (Cab, Petit Verdot, Cab Franc). You can taste at the horseshoe- shaped bar or on the sweeping, sunny patio overlooking the Santa Lucia mountains. 
Just down the road is Linne Calodo, whose soaring tasting room (it looks like half of a huge A-frame) is the place to try inventive blends of Zin, Syrah, and Mourvédre with suggestive names like Problem Child and Outsider.

Come evening, head back to SLO for drinks at Granada Bistro, a jewel-box restaurant-lounge smaller than most living rooms and much more romantic too. Ask about their cocktail specials, or order from the wine list—every glass is $8. Later in the evening, there's live music in an adjacent room. For dinner, walk two blocks to Novo Restaurant and Lounge, where the menu runs the global gamut—Korean short ribs, duck mole, pesto ravioli. If the weather's good, sit on the patio overlooking San Luis Obispo Creek.

Spend your last day outdoors. Start with a hike at Montaña de Oro State Park out on the coast. The Bluff Trail is an easy option with a wide, flat path overlooking the ocean for the entire 3.4-mile roundtrip and offshots where you can meander down to the tidepools below. For a more strenuous thrill, turn off the start of Bluff Trail toward Valencia Peak. It adds 1,250 feet of elevation to the hike, but the 360-degree views from the top are worth it.

Just south of Montaña de Oro in the town of Avila Beach is Sycamore Mineral Springs Resort, a quintessential California coast hideaway fed by underground mineral springs. You don't have to stay overnight in order to use the private outdoor hot tubs built onto a steep hill or the pool fed by waterfalls. Weekend rates are just $17.50 
an hour for each person.

Exercised and refreshed, have a hearty dinner back in SLO at Ciopinot Seafood Grille, a popular spot with a no-corkage-fee policy. Should you not have your own bottle, though, you can order from an endless list of local wines to accompany oysters, tapas, and incredibly fresh seafood entrees including, of course, cioppino. For dessert, shed your foodie snobbery, and split the Butterfinger ice cream pie. It won't disappoint.