IT’S A WONDER there aren’t more accidents on Santa Barbara’s beach-hugging Highway 101. With postcard-worthy views of the Pacific to the south (yes, south—Santa Barbara owns one of the few equator-facing shorelines on the West Coast) and the shadowy Santa Ynez Mountains to the north, the 8-mile trip from Santa Barbara’s palm-studded municipal airport to downtown is fraught with neck-craning distractions.

Despite SoCal’s reputation for ornery commuters, none of the Saturday-morning drivers I’m sharing the road with seem to be in a hurry. “Wow,” I breathe to my sister, Tami, as we parallel West Beach, where an impossibly perfect blue sea laps against the mile-long stretch of sand. “I see why they call this place the American Riveria.”

But this laid-back beach town (pop. 92,000), with its 300 days of sunshine and average highs of 72, isn’t all sand and sea. Beyond the live-oak-cloaked peaks sits a world-class grape-growing region: the Santa Ynez Valley, made famous in the popular 2004 indie film Sideways. The area’s unique topography—the east-west-running Santa Ynez and San Rafael mountains—funnels cooler ocean air into the valley, lengthening the growing season and creating the ideal conditions for cultivating Portlanders’ favorite grape, pinot noir, along with Rhône varietals such as syrah and viognier. Currently more than 80 vineyards are spread among the area’s four AVAs.

Any winter-weary Portlander on a visit here faces a tough choice, given that a journey to the vineyards is, at minimum, a 45-minute drive away from the beach. Fortunately, Santa Barbara’s burgeoning Urban Wine Trail, a tour of tasting rooms inside city limits, offers the best of both worlds. Initiated in 2006, the trail added three more wineries last year, bringing the total to 11, six within a cork toss of the beach.

After settling in at the hipster-ific Presidio Motel—a modest, centrally located spot with decal-decorated walls—Tami and I began our vino adventure at Jaffurs Wine Cellars. Set on the east side of town, this family-owned winery crafts its highly regarded syrahs on-site from grapes grown largely in the Los Alamos and Santa Maria valleys, and neighboring Santa Rita Hills. “When people write about syrah, they call him,” said our convivial host, Roger, motioning toward a photo of owner Craig Jaffurs, a grape-loving surfer featured three times in Wine Spectator.

A few blocks away, Carr Vineyards & Winery’s cavernous tasting room boasts a lively scene: young people clustered around the horseshoe bar, indie rock, and a party ambience (enlivened on our visit by Captain Jack’s wine-tasting shuttle, whose revelers had clearly gotten the most out of their $50 boarding pass).
The wine list, however, promises plenty for the oenophile. Pours range from the clean, crisp 2009 Turner Vineyard pinot gris to the tobacco-tinged 2007 cabernet franc, awarded 95 points by Wine X magazine and a steal at $30 a bottle.

We emerged from Carr just as the sun began to slip, and headed for dinner at the Boathouse restaurant at Arroyo Burro Beach. Blessed with myriad tide pools and small waves, the two-mile-long beach promises hours of family-friendly activity. It’s a favorite spot for locals, many of whom had stashed their surfboards and joined the throngs at the Boathouse’s outdoor bar, where mesquite-grilled seafood can be savored beneath a sunset coloring the sky a thousand shades of pink.

The next morning, we ditched the rental car in favor of the Presidio’s free turquoise beach cruisers. (Santa Barbara is laid out in a very bike-friendly grid.) Fortified by French toast from Tupelo Junction Café, we whizzed down State Street, a popular shopping district, to the heart of the Urban Wine Trail.

Here, sandwiched between city and the sea, six wineries perk up five blocks of industrial landscape. Oreana, a cute little tasting room housed in a former tire shop, helped instigate the wine trail in ’06, although back then owner Christian Garvin called it Cellar 205 and several boutique winemakers shared the space. The true original, though, sits across the street: Santa Barbara Winery. At 38 years old, it’s the area’s oldest winery—unless you count the vineyards at Santa Barbara’s Mission, which were planted by Franciscan friars in 1782 for ceremonial wine.

Around the corner, tiki-themed Kalyra Wines claims a large cult following: Sideways fans will remember Kalyra as the vineyard where Miles and Jack met the sexy Stephanie (Sandra Oh). But the sleek, modern space at syrah siren Kunin attracts the biggest crowds. You can take a break from the masses at Municipal Winemakers, whose funky, eco-conscious approach to wine sampling (tasting notes come on iPads at this paper-free winery) woos visitors almost as much as their Dark Red, a full-bodied shiraz-cabernet blend.

By the time we untangled ourselves from Muni’s grapey grip, there was barely time to cruise to East Beach, a popular haunt where dozens of volleyball courts inspire hope of sighting an Olympian. (Rumor has it gold medalist Todd Rogers practices here.) But the only things on display that day were a handful of beautifully bronzed wannabes, picnicking families, and the ever-present oil rigs, hulking two miles offshore and drawing up 18 million barrels of crude annually.

When the sun rose on our final day, Tami and I traded wine for waves, munching breakfast burritos from Ledbetter Beach’s Shoreline Beach Café, with our toes buried in the sand, hardly uttering a word. But as I swilled my last sip of coffee, I spied three dorsal fins offshore and squealed, “Look!”

Just beyond the whitewash, where sunshine winked off the crystal blue waters, three darting, dancing dolphins gracefully sliced through the waves, flipping and grinning, as though they hadn’t a care in the world. And in easygoing Santa Barbara, they surely don’t.