THE ONLINE POSTING for weekly bike rides organized by Santa Barbara’s most elite road cycling club, Echelon, reads: “Depending upon how the local egos are feeling … the pace can be anywhere from a piano cruise at 18 mph to a blazing 30+ mph.”

On the second day of our stay in Santa Barbara, I and my lapsed-mountain-bike-racer boyfriend, Todd, considered joining the peloton—after all, Lance Armstrong and the Discovery team (later the US Postal Service crew) used to train on these picturesque slopes. Ultimately, we decided against a day of extreme quad burning; to properly enjoy this beach town sandwiched between the Pacific Ocean and the Santa Ynez Mountains, we preferred traveling at a more leisurely pace.

We embarked on a 15-mile loop ride, which circles east through the mountains’ foothills and the neighboring town of Montecito. First, we pedaled into Sycamore Canyon, a mile-long road shaded by hulking eucalyptus trees and, as its name would suggest, the occasional sycamore. As we gradually climbed the rim, shade gave way to a prickly-pear-and-palm-lined street and a sunbaked neighborhood filled with the lush, manicured grounds of estate homes. We could see the Pacific only intermittently, but we felt the breeze wafting in off the water. From what I hear, this was a typical Santa Barbara day: sunny, cool, with bluebird skies blessedly free of smog.

Santa Barbarans openly eschew LA’s sprawl in favor of SoCal’s version of Portland.

We swung onto Mountain Drive (an official city-designated bike route) and found ourselves among villas with red-tiled roofs surrounded by green lawns and stands of cypress trees, separated by low-slung stucco walls. We found out later that there’s a reason this neighborhood resembles an Italian village: In the 1800s a cadre of wealthy Midwesterners moved here, bringing with them their expert gardeners and stonemasons, many of whom were Italian.

An ideal climate and Mediterranean aesthetic, it turns out, are just ancillary reasons to visit this classy Southern California community of 90,000. Its slow pace, small-town feel, and unspoiled landscape have made Santa Barbara the anti-LA of Southern California, and are the reasons why celebrities, from Charlie Chaplin to Oprah Winfrey, have retreated here since the 1920s.

In fact, locals openly eschew the sprawl of their southern neighbor in favor of a more intimate coffee-and-bike culture: California’s version of Portland, if you will. “We have a different attitude and views here,” says Ralph Fertig, president of the Santa Barbara Bicycle Coalition, an advocacy group that promotes bike commuting. He says the community is bent on preserving its history while ensuring its future is free of another freeway or scads of ticky-tacky condos cluttering the coastline. “We always say, ‘Don’t let Los Angeles happen to us.’”