My San Francisco: An Honest First-Timer's Guide From Someone Who Learned on the Ground

Quick Answer

San Francisco is one of the most rewarding city breaks in the United States. You get world-class food, incredible neighbourhoods, iconic landmarks and some of the best bars you will ever sit in. The hills are real and relentless, so use the cable cars and trams rather than your legs. Stay close to Union Square and know which neighbourhoods to avoid. The Tenderloin is not a place you want to wander into by accident.

I went to San Francisco in the late 1990s, early 2000s, for a Macromedia conference. I tacked a few days on before it started and a few days on after it finished, which is always the right move when you're flying that far. San Francisco is on the west coast of the United States, so it's a long haul from the UK. But the time difference works in your favour on arrival. I landed and got to my hotel at about two in the afternoon, dropped my bags, and walked straight out into Union Square in the sunshine.

Union Square was a couple of hundred yards from my hotel. Ten minutes into my first afternoon in San Francisco, I was in America. Really in it.

Photo: Navlakha / Pexels

The Irish Bar, the Geordie, and the Scottish Piper

I was thirsty after the flight, so I started looking for somewhere to get a beer. The first place I spotted was an Irish bar. Of course it was.

I sat down and ordered. From the next stool along, I heard it. That unmistakable Geordie accent. There he was: a fellow Geordie, sitting in an Irish bar on the west coast of America. We got chatting and he turned out to be a genuinely good bloke. He had a lot of good knowledge about the city, so I listened carefully.

He asked where I was staying. I said not far from Union Square. He nodded and said there were a couple of things I needed to watch out for. The Tenderloin, he said, is right on your doorstep. If you go around the wrong corner, you'll find yourself in a part of San Francisco that's best described as rough. People sleep in doorways, and if you linger you will get mugged. Don't linger. Know where you're going and keep your map handy.

He also pointed me towards a bar called the Gold Dust Lounge. Just head towards the Mission end of the street, he said. You'll find it.

And then there was the piper. Because this Irish bar had a piper in the corner. Not an Irish piper. A Scottish piper. Black Watch, I think. I have absolutely no idea why. But there he was, playing away in the corner of an Irish bar in San Francisco. Don't let anyone tell you it was an Irish piper. It wasn't.

The Gold Dust Lounge

I said goodbye to my Geordie friend and wandered down to the Gold Dust Lounge. And what a place.

It was a proper American bar, full of locals, a bit like something out of Cheers. The owner was behind the bar doing his party piece: flicking bottle caps into a bin on the other side of the room. Every time. Full of quips, full of banter, talking about the baseball at the weekend.

But the bartenders were the real story. Mostly students, quick and funny, genuinely great people to talk to. They had a system I'd never seen before. There was a tray running along the front of the bar, closest to the customers. As long as you kept putting a dollar in the tray, they would keep coming back to you. They'd take the dollar as a tip, pour your drink, and keep moving. You'd put another dollar down when you were ready for the next one. No catching someone's eye, no waving. Put a dollar in the tray and they were back. It worked brilliantly.

I was sitting there at about five in the afternoon, getting properly into the swing of things, when I noticed something odd. A group of maybe ten people came back through the door. All of them had been outside having a cigarette. Still smoking. Lit cigarettes, in a bar where indoor smoking was banned.

I asked one of the bartenders what was going on. She told me the smoking inspectors knock off at five o'clock. So from five onwards, nobody's checking. And a few of the inspectors, she added, would probably be in for a smoke themselves later.

I found that very San Francisco.

Photo: Johan van Geijl / Pexels

Biscuits and Blues

After the Gold Dust Lounge I went back to the hotel, freshened up, and thought about the evening. My Geordie friend had mentioned Biscuits and Blues. It was a basement blues bar near Geary Street, not far from where I was staying.

I headed over at about ten o'clock. I have a habit of only just getting going around that time.

It was absolutely fantastic. Down some stairs, into a basement room, and there was a proper blues band on stage. Real blues guitar. The smoky, gritty kind that you feel as much as hear. The kind of place that reminds you why people write songs about being somewhere. I tipped well, stayed late, and left very happy. A perfect first evening in San Francisco.

The Week in the City

The weekend before the conference started, I got out and explored. Cable cars everywhere. I will come back to that, because the hills make them essential. I found Chinatown heading up the bank towards the coast, ate in a couple of Chinese restaurants, and worked my way around several districts.

I had heard, through various tech forums and hacker publications of the time, that there was a pizza place called Blondie's Pizza that was supposed to be something special. I found it. It was extraordinary. Proper pizza, made properly. Infinitely better than any of the big UK chains. I bought a Blondie's t-shirt in commemoration, which I felt was completely justified.

Coming out of the conference one afternoon, I wanted a steak. If you're in America, you should eat a proper American steak. I was looking around trying to work out where to go, when I noticed a row of police motorcycles parked up outside a building. I thought: if it's good enough for them, it's good enough for me.

I went in. There were police officers in full uniform, helmets hung up on the rack, sitting at the counter. The man behind the grill was a showman. When the cop next to me ordered a steak, a 32-ounce something-or-other, the chef reached into what looked like a bucket of blood, pulled out this enormous piece of meat, and slapped it down on the grill. The fire went up. The whole place smelled incredible. It was pure spectacle.

I did not order a 32-ounce steak. I had a steak burger, some fries, and chicken wings with blue cheese sauce. It was brilliant.

Photo: Alexis Ricardo Laurin / Pexels

Pancakes, Maple Syrup, and a Long Time Ago

For breakfasts, I found a 1950s American diner. The real thing: black and white tiled floor, pinball machines, an old jukebox with neon tubes, the whole lot. Like something straight out of Happy Days.

I ordered pancakes and maple syrup. I had never done this before. Sweet pancakes, maple syrup, bacon on the side if you wanted it. The whole concept was completely alien to me. I was from Newcastle. We did not do this. I ordered it, ate it, and it changed my life in a small but meaningful way. I went back every morning.

American food, in general, was a revelation. The UK at that point had McDonald's and Burger King and not much else. San Francisco had Wendy's, Jack in the Box, and dozens of smaller local chains that were producing food at a quality level that the big names couldn't touch. Blondie's Pizza is the headline example, but it extended to everything. The food was better, cheaper, and more varied than anything available at home.

Star Wars, an Opening Night, and a Very Excited Audience

During my stay, Star Wars: The Phantom Menace opened in San Francisco. There hadn't been a new Star Wars film in years and years, and the anticipation was enormous. I called the hotel concierge, got a ticket for a few days later, and went along by myself to one of the big cinemas.

I will never forget it.

The place was full. The lights went down. The curtains stirred a little and then hung still. The whole cinema went silent. You could feel the tension and the expectation from every single person in the room. Everybody knew exactly what was coming. Everybody was holding their breath. Then the curtains opened, the music started, and the place erupted. Whooping, hollering, people out of their seats.

In a British cinema, everyone would still be sitting there going. In San Francisco, the entire audience lost their minds. I couldn't help joining in. Fear of missing out is a powerful thing.

Photo: David Vives / Pexels

Alcatraz

You cannot visit San Francisco and skip Alcatraz. I did not.

There is a guided audio tour. In my day it was a cassette walkman, headphones in, following a taped recording as you walked around the island. The format was brilliant regardless of the technology. Voices of former guards, voices of former prisoners, telling you what it was like. Al Capone's cell. The gun towers. The story of every escape attempt.

Nobody escaped from Alcatraz. Some people say they did. They did not.

It is a sobering place. It is also a fascinating place. Worth every minute.

First-Timer's Guide: What I'd Tell Anyone Going to San Francisco

• Stay near Union Square. It's central, well-connected, and puts you within reach of almost everything. You will know when you're drifting towards a rougher area. You will see people huddled in doorways and the atmosphere will change. Trust that instinct.

• Avoid the Tenderloin. It was a rough neighbourhood when I was there, and the reputation has not improved. It sits right next to Union Square, which catches people out. Know which direction you're heading before you start walking.

• Use the trams and cable cars. San Francisco's hills are not a joke. The hills are real and they are steep and they go on longer than you think. Nobody wants to walk up from downtown to Nob Hill in the afternoon heat. The transit system is good. Use it. It's also part of the experience.

• Alcatraz is worth it. Book ahead. Do the audio tour. Don't leave thinking you'll do it on a future trip.

• Eat at the smaller places. The big chains are there but the quality of the smaller independent restaurants and local chains is in a different league. Ask where the locals eat and go there.

• The film locations are real. Bullitt was filmed on those hills, on those exact streets. If you're a film person, it's worth knowing where to look.

Frequently Asked Questions About San Francisco

Is San Francisco worth visiting?

Absolutely. It’s one of the most rewarding city breaks in the United States. World-class food, incredible neighbourhoods, iconic landmarks, and a character unlike anywhere else. Ten days there felt like barely scratching the surface.

What’s the best area to stay in San Francisco?

Near Union Square. It’s central, well-connected, and puts you within easy reach of almost everything. The cable car lines run from there, Chinatown is a short walk, and most of the classic bars and restaurants are nearby.

Is the Tenderloin safe?

It’s best avoided. The Tenderloin sits right next to Union Square, which catches visitors out. People sleep in doorways and the atmosphere changes quickly. Know which direction you’re heading before you start walking, and trust your instincts if something feels off.

Do you need a car in San Francisco?

No. The cable cars and trams cover the city well, and the hills make walking impractical for longer distances. The transit system is part of the experience. Use it.

Is Alcatraz worth visiting?

Yes, without question. Book ahead, do the audio tour, and allow a good half-day. The voices of former guards and prisoners make it genuinely immersive. Don’t leave it for a future trip.

When is the best time to visit San Francisco?

September and October are often the most reliable months. Expect clearer skies, warm afternoons, and the famous summer fog has usually lifted by then. Spring is also good. Avoid expecting classic sunshine in July and August; the fog is a real feature of the Bay Area summer.

How many days do you need in San Francisco?

A minimum of five days to cover the highlights. A week to ten days gives you time to explore beyond the centre. Day trips to Marin County, Napa Valley, or along the coast are well worth adding.

One Last Thing

I spent about ten days in San Francisco in total. I barely scratched the surface. I didn't get out to Marin County, where George Lucas has his ranch somewhere. I didn't make it to Napa Valley. I've been told the wine is extraordinary and I intend to go one day, because I take wine fairly seriously. I stayed close to the conference and the city centre, and I still had one of the best ten days I can remember.

San Francisco gets under your skin. I don't know how else to put it. I've been to a lot of cities. San Francisco is one of the best.

If you're thinking about going, go. And if you want help putting the trip together, you know where I am.

Warren Milburn is the founder of Kite and Compass Travel, an independent travel advisory business based in Newcastle. He has forty years of experience in travel and systems-thinking and has been to San Francisco so he knows what he is talking about.