Discover the American Riviera by Train

There's no way I'm reading now that the train has reached the ocean.

I look out from the Pacific Surfliner at Pacific surf riders: longboarders and shortboarders, paddle surfers and surf kayakers. There are dolphins too, glowing in sunlit waves.

I imagined that the train would race by unnoticed, but the surfers turn toward the tracks. One straddling his board raises his arms, both hands splayed in an enthusiastic shaka salute.

His message, of course: Hang loose.

Which is exactly what my wife and I are doing on a train rolling through our own Southern California backyard.

STOP 1: SAN DIEGO

There's something liberating about being out of the car, free to discover the people and places in that big world between point A and point B. We get quick affirmation of that notion as we disembark at San Diego's 1915 Santa Fe Depot: We come face to face with revenge of the nerds on a metropolitan scale. We have stumbled through the looking glass and into Comic-Con, the annual gathering of pop-culture tribes: comics freaks, sci-fi buffs, and anime obsessives among them. While people-watching is one of the best parts of seeing a city on foot, we had hardly expected this quality of street theater.

Nor had we expected to get diverted even before reaching our hotel. But it turns out the train station's old baggage room is a gallery space of the Museum of Contemporary Art San Diego. Burdened with our luggage, we must take turns seeing the exhibits before heading to our hotel in the Gaslamp Quarter – less than five minutes by cab and one of downtown's best-preserved areas, with all of its Victorian and Queen Anne buildings.

After checking in, we walk along Fifth Avenue, swimming upstream against Comic-Con goers emerging from the convention center, before bailing for lunch at Bondi, an Australian-themed restaurant.

As the day ebbs, we walk in and out of stores, the character of the streets changing as we stroll. We eventually wander into Little Italy, once home to tuna fishermen and now an enclave that combines markets and restaurants with modern lofts. We come upon Anthology, a music venue that sets the vibe of a 1940s supper club in a multilevel contemporary space with audio fetishist–quality acoustics.

For years, I've had a knack for missing jazz legend Mose Allison, but in a nice bit of luck, he's playing here tonight. Allison races through his classics, a human in shuffle mode, his voice still hipster cool.

We consider cabbing back to the hotel but decide to walk, extending our improvised day. I can't say San Diego is quite a 24/7 city à la New York, but past midnight, the Gaslamp is still hopping, so we're giving it a go.