We didn’t wake up until about 10:30 this morning. Jane wasn’t feeling great—probably thanks to the human foghorn coughing and spluttering all over the bus yesterday as we passed through Chinatown. Credit to her, though—she kept going for as long as she could.
We’d planned to tackle Lombard Street today, famously dubbed the “crookedest street in the world”. But first, we had to walk down into SoMa—South of Market. And wow, that area turned into a bit of a dive real fast. It was like stepping into a different city entirely. The glossy storefronts vanished, replaced by a gritty, retro vibe straight out of a 1970s cop show. Seedy shops, tired buildings, and a general sense that we’d wandered off the tourist map.
Thankfully, we didn’t have to wait long for the bus. But once we reached the stop and looked up at the ridiculously steep side streets we’d need to climb to reach Lombard, we quickly reconsidered. Jane’s leg wasn’t up for it, and frankly, I wasn’t convinced mine was either. So we did the sensible thing—hopped back on the bus and rode it to the end of the line, and ended up at Ghirardelli Square instead.
Chocolate Treats – Ghirardelli Square
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| Ghirardelli Square Fountain |
The main event today? Chocolate. Glorious, decadent, historic chocolate. Ghirardelli Square is home to not one, but two Ghirardelli Chocolate Shops. And yes, they hand you a free sample as you walk in. So naturally, if you visit both, that’s two free chocolates. But what happens if you try to sneak in a third time? Turns out, they’re onto that game. We only went back in to use the lift down to the lower street level—purely to avoid the steep hill. Honest. Totally not angling for a third chocolate. Much.
The square itself is steeped in chocolatey lore. Back in 1893, Domingo Ghirardelli—an Italian-born chocolatier who’d already made a name for himself in San Francisco—bought the entire city block to house his chocolate empire. Fast forward to the early 1960s, and the company was acquired by the Golden Grain Macaroni Company (because apparently, pasta and chocolate are a match made in corporate heaven). They moved production elsewhere and put the prime real estate up for sale.
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| Chocolate Heaven |
Enter William M. Roth and his mother, Lurline Matson Roth—local legends who weren’t about to let the square become just another apartment block. In 1962, they bought the land and hired a team of visionary architects to transform the old brick buildings into a vibrant complex of shops and restaurants. It was the first major “adaptive reuse” project in the U.S., and when it opened in 1964, it set a precedent for preserving historic spaces.
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| Fountain In The Square |
In 1965, the lower floor of the Clock Tower got a stylish makeover by Benjamin Thompson and Associates, who kept the original architectural charm while turning it into a Design Research store. That space eventually became home to the main Ghirardelli Chocolate Shop—a full-circle moment if ever there was one.
Today, Ghirardelli Square is a lively mix of boutiques, restaurants, and chocolate-fueled joy. You can sip hot fudge sundaes while gazing out at the bay, wander through historic passageways, and even spot the original 19-foot “G” from the iconic sign inside the shop.
After a couple of hours of wandering (and resisting the urge to buy every chocolate in sight), Jane was feeling worse, so we hopped on a bus back toward the hotel. A quick stop at Walgreens for some medicine, and I dropped her off so she could rest. I even managed to sneak in an hour myself. Tough job, but someone had to do it.
Return to Lombard Street – A Solo Ascent
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| Looking up Lombard Street |
Feeling a bit under the weather myself, I opted for a gentle potter to round out the afternoon. I hopped back on the number 19 bus and retraced our earlier route, this time determined to conquer the infamous incline of Lombard Street—what I like to call the “west face.” It’s not Everest, but it certainly felt like it.
The climb was no joke. Lombard Street’s crooked section—between Hyde and Leavenworth—is world-famous for its eight tight hairpin turns, designed in 1922 to tame a natural 27% grade that was simply too steep for early cars. The street drops about 200 feet in just one block, and it’s so steep they’ve installed steps along the side for pedestrians who don’t fancy sliding down like a human toboggan.
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| View Towards The Bay Bridge from Lombard St. |
Despite the dizzying angle, the houses lining the street are charmingly defiant. Their postage-stamp gardens are immaculately kept, tucked into the bends like little green punctuation marks. I couldn’t help but admire the dedication it must take to maintain them—equal parts horticulture and mountaineering.
From the top, the views were nothing short of breathtaking. As I stood there catching my breath—partly from the climb, partly from the sheer beauty—I felt a kind of stillness settle in. Hyde Street stretched out below like a ribbon unraveling through Russian Hill, leading the eye straight to Alcatraz, sitting quietly in the bay like a ghost of history. The late afternoon light painted everything in soft gold, and for a moment, the chaos of the city faded into the background. It was one of those rare travel moments where time seems to pause—where the view isn’t just something to look at, but something that reaches inside you and stirs something unspoken. I felt small, but in the best way. Like I’d stumbled into a scene that had been waiting patiently for someone to notice.
Tech & Beer – A Local’s Afternoon
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| Russian Hill Heading to lombard Street |
After watching cable cars zip past the top of Lombard Street—and taking far too many photos of them (they’re just so photogenic!)—I decided to keep things low-key. The queue for the cable cars up there was its usual epic length, so I did the sensible thing and walked down the hill toward Washington Square. From there, I hopped a bus back to Market Street and grabbed a sandwich from a shop.
There was something oddly comforting about sitting in Walgreens, munching on a store-bought sandwich and watching the world go by. “Is this what it’s like to be a local on your lunch break?” I wondered. That’s something we try to do more on holidays now—live like locals. No fancy-pants restaurants, no curated experiences. Just sandwiches, street corners, and a bit of quiet observation.
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| Union Square Cable Car |
With no grand plan for the rest of the afternoon, I wandered into the Apple Store—my first time inside one of their glossy temples of tech. I don’t own any “fruit-based products” myself, and certainly couldn’t afford one, but the staff were friendly and chatty. They clocked I was from the UK straight away and explained how they could sort out the tax paperwork for international purchases. Apparently, buying something pricey here means you’ll pay more than you would back home—unless, of course, you “accidentally” lose the box and casually stroll through customs like every other phone-carrying traveller. That suggestion earned me a knowing smile. Clearly, I wasn’t the first to float that (purely hypothetical!) idea.
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| Union Square |
Later on, I popped into Johnny Foley’s Irish Pub, just off Union Square. It’s a bit of a plastic pub but warm, lively, and packed to the rafters. Despite the crowd, I managed to find a spot to stand with my pint. What always impresses me about American bars is how efficient the service is. Even when it’s heaving, you still get served quickly and in the right order. While one drink’s pouring, they’re already taking the next order. It’s a rhythm some UK pubs could definitely learn from.
After a couple of well-earned drinks, I’d had enough for one day. Back to the hotel, back to the TV, and most importantly, back to a big comfy bed to sprawl out on. A perfect end to a day of local living, tech window-shopping, and a pint among the crowd.
Reflections – Living Local, Thinking Global
There’s something quietly satisfying about a day with no grand agenda. No bucket-list ticking, no pressure to “make the most of it”—just a gentle meander through someone else’s city, trying it on for size. From Walgreens window seats to Apple Store hypotheticals, it was a day of small moments that somehow felt big.
I didn’t buy anything flashy. I didn’t ride the cable car. I didn’t even sit down properly at the pub. But I did feel like I was part of the rhythm of the place, even if just for a few hours. That’s the kind of travel I’ve come to love most—not the highlights, but the in-betweens. The sandwich breaks, the tech temptations, the pint in a crowd.
And maybe that’s the real souvenir: the feeling of belonging, however briefly, in a city that’s not your own.