San Francisco: Pack Shorts and You’ll Be Buying a Hoodie by Lunchtime
Somebody once said their coldest winter was a summer in San Francisco. Mark Twain usually gets the credit, though I wouldn’t put his name to it. Whoever said it understood the danger of packing for California on the strength of the word California.
I can picture the transaction at Fisherman’s Wharf. It’s eleven in the morning, the flip-flops are still on, and suddenly a sweatshirt that says “I Left My Heart in San Francisco” looks worth every cent.
Capetonians will understand. We have the cloud that spills over Table Mountain and calls itself a tablecloth. San Francisco has Karl. The fog comes in over the Golden Gate on its own schedule. I’d pack a layer and let Karl get on with it.
By Rob Wheatley
Bells, barks and a taxi with nobody in it

I’d recognise San Francisco with my eyes closed. There’s the foghorn across the bay, the cable car bell and the Pier 39 sea lions sounding like grumpy old men arguing about football. Then a driverless taxi glides by in near silence. That still feels like science fiction to me.
The bridge, the prison and a very crooked street
Golden Gate Bridge. International Orange sounds like something you’d order at breakfast. On a clear day the bridge looks like a film set. In fog the towers can disappear while you’re still walking towards them. I’d walk partway across and turn back whenever I’d had my fill. As a skipper, I’m quite happy to admire the currents below from somebody else’s boat.

Alcatraz. The cellhouse audio tour lets former prisoners and officers tell the story. I’d book the ferry ahead and leave room in the day for the island. It leaves from Pier 33. Check the National Park Service visitor information before you go.
Cable cars and Lombard Street. I’d take a cable car for the clanging, the climb and the sheer improbability of the whole thing. At Lombard, walk the steps beside the eight bends. You get the view and the drivers do the sweating.
Fisherman’s Wharf and Pier 39. I’ll put up with the crowds for the sea lions. Watch them shove one another off the platforms and tell me you’ve never seen a committee behave like that.
Where I’d wander once the icons are done
Chinatown and North Beach. I’d start at the Dragon Gate, give myself time for the side streets and dim sum, then wander into North Beach for City Lights and an espresso. An outdoor table is as far as my imaginary novel usually gets.
Haight-Ashbury and Alamo Square. I’d browse the record shops and vintage racks around the Haight, then give the Painted Ladies their own stop. Alamo Square is a good spot to sit and watch the skyline behind the houses.
The Mission and the Castro. I’d make time for the Mission’s murals and Dolores Park. In the Castro, give the streets and their LGBTQ+ history time of their own. These are neighbourhoods I’d happily spend an afternoon walking.
Golden Gate Park. I’d pick a garden or museum, then go looking for the bison. There’s something pleasing about being in a major city and having to say, quite seriously, “Shall we go and find the bison?”
What I’d eat with my sleeves rolled up
I’d start with chowder in a sourdough bowl. Then I’d save a proper appetite for a Mission burrito. I like the optimism of anyone who thinks they’ll get through one without making a mess.
If Dungeness crab is on the menu, I’d ask what’s available and sacrifice the clean shirt. When the fog comes in, an Irish coffee at the Buena Vista sounds about right. If I’ve still got room after that, there’s always a Ghirardelli sundae.
An evening with a good seat
North Beach would get my vote for a nightcap, the Mission for dinner and music, and the Fillmore if there’s a band I want to hear. The Castro has plenty of life after dark too. If I find a rooftop with a view, I’ll keep the jacket on and stay a little longer.
At a Giants game, I’d be tempted to watch the kayakers in McCovey Cove waiting for a home run. I know perfectly well there’s a game going on. The boats still win.
When I’d cross the bridge
Muir Woods. I’d go for the redwoods and the change of pace. Reserve parking or the shuttle ahead if you’re using either. Sausalito suits a quieter half-day by the water. Check the ferry timetable before deciding how to get back.
Napa and Sonoma. I’d give wine country a day of its own. Pick a few stops and arrange a driver or a tour if you’re tasting.
The bits I’d sort before leaving home
- Pack layers and shoes with grip. Leave room for a windy waterfront and an uphill walk in the same afternoon.
- Check the slope as well as the distance. A short walk on the map can feel rather longer with luggage. I’d check the route from the transit stop to the hotel door.
- Price the whole stay. Compare room costs, parking if you need it and what you’ll spend getting around. Budget for tips where applicable.
- Keep a parked car clear. Take bags and valuables with you and leave the cabin empty of visible belongings.
Choose where you’ll wake up
I’d come for the bridge and stay for the neighbourhoods. The city feels different when you can walk out of the hotel and straight into the part you came to enjoy.
Next step: Compare four areas to stay in San Francisco or go straight to the Neighborhood Finder. Planning a wider trip? See my USA travel guide. Take the sweatshirt. Karl usually gets the last word.