Our Day Trip to San Francisco
“This is a world-class city. I get we’re taking it on the chin at the moment; but, it doesn’t change the fact that this is a world-class city.”
On our day trip to San Francisco, we found ourselves sitting at the bar, eating pizza at the iconic North Beach haunt, Sodini’s, and his name was Kyle. He was well-dressed in simple black slacks and a polo-style shirt; his demeanor was humble and unassuming–much like the restaurant we were in. He had been a cameraman for the PGA Golf Tour and lived two blocks away. His work had taken him through the most beautiful cities the world has to offer, but San Francisco is the one he chose to retire to. It was a sentiment that we had heard several times throughout the day.
We had started this journey at 4:00 a.m., the previous morning at Drake’s Bay; the shroud of fog from the night before had been melted by the sun and the remaining mist painted the sky with a dazzling array of color bursts and pops, each appearing like snowflakes, big enough to capture on your tongue.
Gypsea Explorer, our Scepter 41 Sailboat, gracefully navigated around the Marin Headlands, its rolling hills of coyote brush and sage broken only by the sound of a distant foghorn. Dramatic cliffs of oceanic rock gave way to the red-roofed building of the Bonita Point Lighthouse.
Soon Alcatraz came into sight, and you could hear the whispers of its complex history and stories sift through the air. And then, we are slipping under the Golden Gate Bridge. Up to this point, we had been sailing, learning, growing, seeing beautiful things, meeting interesting people–but, as the International Orange, mile-wide suspension bridge loomed in the distance: Sailing, suddenly FELT real; as if time had curved back on its self–and had become irrelevant–maybe even unnecessary. The experience took a minute, which felt like an hour–in which time we became sailors.
We had decided that on Sunday, we would play tourist in San Francisco. It was a day I was looking forward to.
I had lived in the City in the 80s; straight out of high school; straight out of a town that does not–according to Google– “have much information about population or demographics of the past.” It was small. I was 18 and attended USF, University of San Francisco, a private Jesuit school. I lived in Phelan Hall, now renamed to the much more politically correct Burl A. Toler Hall. When I went, there was a wing called, The French Annex, filled with beret-wearing, cigarette-smoking folk, foreign speakers, direct from France. At the time, their unhygienic manners elicited a need for their wing. I was not one of the upper echelons awarded entry to the institution via a trust fund or silver spoons. I arrived with a hodge-podge of scholarships and a deeply embedded work ethic. My days consisted of classes and lectures; pop quizzes and exams. At the end of each day, I would shuffle to the bus and deliver myself to Clown Alley on Lombard and Divisadero, serving hamburgers and fries under the watchful eyes of a circus clown. During this time, I fell in love with San Francisco; and although she kicked my ass in the 80’s, I determined I would come back to her when I was an adult and enjoy her on her terms. Over twenty years later, I did just that.
Today, I love sharing the city by the bay with people to show them a side of San Francisco that the media refuses to.
Me and The Kiwi had a slip at Jack London Square in Oakland. It was a perfect, sunny day when we got up and caught the ferry to the City.
First Stop: The iconic Boudin at The Wharf, for a Bloody Mary and a Sourdough Bread Bowl; of which neither disappointed. The service was exceptional, the view stunning, and the Bloody Mary and Chowder were terrific. I have not been able to make this type of sourdough on Gypsea!
Second Stop: The Buena Vista for–what else? Irish Coffee! We were early enough to stand for only 5 minutes before getting a seat at the bar. The Buena Vista, which opened in 1916, is credited with introducing Irish Coffee to the United States in 1954. They make about 2000 Irish Coffees a day; but, as we were early, the bartender was making only a couple at a time. I said I was hoping to see him make 35 or 40 and he jokingly suggested we buy a round for the bar, and then he would! At $14.00 a pop, we would have to mortgage our Sailboat!
Third Stop: The Saloon, a cash-only, amazing blues dive bar with $5.00 beers. It’s the oldest working bar in San Francisco and stories say that in the 1800s, drunk patrons leaving and weaving down the street risked being shanghaied. The Saloon survived the 1906 earthquake and the following fires because firefighters wanted to save the ‘working ladies‘ upstairs.
Next, we walked through Chinatown. Stockton Street is lined with paper lanterns and flanked on both sides by novelty and souvenir shops; tourists rummaging through bins of multicolored lucky cat figurines and plastic buddhas. Grant Street smells of Asian cuisine and foodstuffs with fish and freshly baked ducks hanging from windows and handmade tarts in pink boxes being poked through unmarked metal gates into the hands of waiting customers. They are very different from each other, and we savored them both.
Onto the FiDi, where we discover an authentic Irish Pub–(Irish Bank). Nestled on an alley lined with vintage signs, Edison lights, and tables, this place is a hidden gem. We cozied up to the bar of dark wood and enjoyed a pint.
Next door is Harlan’s Records–a vintage cocktail bar and audiophile paradise. Walls are covered in vintage records, from John Lee Hooker to Jane Fonda’s Workout Record–(which I still own!). Radios from the 1940s and ‘50s have been refurbished and are on display, and of course, a turntable spins behind the bar. The menu hosts music-inspired cocktails; The Dylan, The Gambler, and Ol’ 45.
As the day ends, we find ourselves, at Sodini’s, sharing the bar with Kyle, in what is undeniably a ‘world-class city.’
Until Next Time!
Fear Less/Adventure More!
S/V Gypsea Explorer
Me & The Kiwi
5 Songs Inspired by This Trip!
“I Left My Heart in San Francisco” Tony Bennett
“Sittin on the Dock Of The Bay” Otis Redding
“San Francisco Nights” Eric Burdon & The Animals
“San Francisco (Be Sure to Wear Flowers in Your Hair)” Scott McKenzie
“When The Lights Go Down in the City” Journey
And, if this tickles your propellor, grab Amazon Prime Music Here–FREE!
Explore My Amazon Store and uncover a world of music, sailing essentials, and specialty items you won’t find anywhere else. Your next favorite find is just a click away!

Written by Heather Jacks
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