San Francisco Travel: Experiencing the historic City by the Bay

San Francisco Golden Gate Bridge Travel


Jack Kerouac probably didn’t have too many flight and luggage problems. 

Maybe I should start at the beginning and perhaps I should travel lighter. 

Still, there was nothing to be done about the ripped airplane wheel causing our flight to San Francisco to be delayed, which led to our connecting flight delay, which was why we had no luggage waiting for us at the San Francisco airport at 5:30 pm on a Wednesday in August. 

To comfort ourselves, we raided the JW Marriott Union Square minibar.

“Be in love with your life, every detail of it” | Jack Kerouac


The next day we walked the short distance to Jasper’s Corner Tap and Kitchen.

Our bags finally found us that afternoon which meant we could wear more appropriate clothing for dinner at the historic Sutro Cliff House. 

Seated next to the floor-to-ceiling windows overlooking the gleaming white “Seal Rocks,” we enjoyed the slowly fading twilight hue on the cold, crashing waves while we lingered over the butterscotch dessert.

“Sutro’s is a stylish yet casual restaurant with floor-to-ceiling windows and stunning panoramic ocean views. Housed in the Sutro Wing, the restaurant draws on the architecture of the Sutro Baths, recalling an era of elegance and grace.” |


San Francisco Travel Guide Road Taken To

The next day, I walked over 7 miles. 

First, to the fairly clandestine red and gold Café Claude on Claude Lane where I had a decadent meal of pasta and a couple of cocktails to loosen the muscles for all the walking that lay ahead.

A block away from the Chinatown Gate, I began my journey through the sometimes seedy yet enticing streets of San Francisco. 

I strolled through the trinket shops to Red Blossom Tea Company where they offer several tea-tasting ceremonies. Wanting to take a small piece of the experience with me, I bought a fragrant blend gathered from the peaks of some unknown, far-off mountain.

I walked everywhere. No place was off-limits. I climbed the Coit Tower and wound my way down to the harbor then on to the City Lights Bookstore where I paused to rest and rake my eyes over the spines of the books.

On…on….on… until my flattened feet decided it was high time to find my way back to the hotel.

“Where are we going, Walt Whitman? The doors close in an hour. Which way does your beard point tonight” | Allen Ginsberg


The only way for us to secure the coveted tickets to Alcatraz was to book a combo Segway tour.

The thought of traversing the congested harbor walk and roadways via Segway seemed like a hazardous idea. 

So, instead of a white-knuckled two-wheeled tour of the harbor, we chose to drive over the Golden Gate to Sausalito for the morning, which was much more interesting than we previously remembered. Mainly because, we actually found the downtown area this time around, parked, and took the time to walk the streets and tour the artsy shops.

The rest of the day, we just drove—back through the streets of San Francisco, then along the chilly coastline with no particular purpose or destination other than to see the never-before-seen.

“The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars”  | Jack Kerouac
San Francisco Travel Guide Road Taken To
“No man should go through life without once experiencing healthy, even bored solitude in the wilderness, finding himself depending solely on himself and thereby learning his true and hidden strength. Learning for instance, to eat when he’s hungry and sleep when he’s sleepy” | Jack Kerouac


Thinking back, it seems a little strange that one of the top San Francisco travel attractions is an old prison. 

Why pay good money to take a frigid boat ride to the middle of the bay to walk around a dank, concrete bunker? And yet, it remains one of the hottest tickets in town.

I guess it comes down to history. A means of understanding and sharing a part of the past here in the present. 

Whether you want it to or not, the experience of walking through the old prison, seeing the dismal dining area, open showers, rows of cramped cells, and the terrifying Cell Block D with its solitary confinement cells haunts you long after you’ve left.

I stood for a moment in one of the D Block cells, and the inky darkness was terrifyingly palpable, suffocating. 

How could the mind and spirit survive in such a hole? I guess it gives you a lot of time to think—to consider what you did to get there—to obsess about how to get out.

San Francisco Travel Guide Road Taken To
“The best teacher is experience, and not through someone’s distorted point of view” | Jack Kerouac

Even if you could escape the prison, how do you survive the deep cold, forceful currents of the bay? The stories of the escapes were fascinating as was the idea of the children of the prison guards and staff who grew up on “The Rock.”

What a life.

We chose to dispel the darkness of the prison with a decadently overindulgent visit to Ghirardelli Square. Chocolate, caramel, and peanut butter, drizzled over scoops of ice cream was our reward for being (mostly) upstanding citizens, as well as a reminder to not dabble in a life of crime in the future.

San Francisco Travel Guide Road Taken To
“At night you could hear the life and sounds of the city as you lay in your prison cell” | “Notes from Alcatraz”

That afternoon, we drove a few hours to the Ritz Carlton Half Moon Bay for an impromptu late lunch, a walk along the golf course to the water’s rocky edge, and finally closed out the evening with a cocktail on the terrace warmed by fire pits and contented humanity.

San Francisco Travel Guide Road Taken To
The Ritz Carlton Half Moon Bay
San Francisco Travel Guide Road Taken To
San Francisco Travel Road Taken To
“San Francisco has only one drawback, tis hard to leave” | Rudyard Kipling

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