An insider’s guide to San Francisco’s more adventurous side

Since heading to the Bay Area for college, Jeffrey Gerson has found no reason to leave. Originally convinced to stay in San Francisco for a job at Instagram, Gerson fell for the city as a home that offered more space, more perspective and an inspiring energy amongst its inhabitants to go after your passion. The effect of the latter led Gerson to focus his efforts on his latest creative endeavor — the La Anna Guesthouse, a creatives' retreat and artist residency in a historic home that Gerson is renovating in Pennsylvania's Pocono Mountains.

While, like many of the city's residents, Gerson worked in the tech industry for a number of years, our local Soho House consultant stresses that it's not the only area in which the city is pushing boundaries. From award-winning restaurants with experimental menus, to hikes a short drive out of the city with hidden artistic gems, San Francisco has plenty to tempt adventurers, whatever their interests. Here, Gerson shares his picks of the city's most exciting spots, as well as those worth making a trip into the surrounding mountains. 

EATING OUT
For dining with a purpose: Cala
‘It’s my holy grail restaurant in San Francisco. Not only do they serve some of the best food in the entire city, but owner Gabriela Cámara makes a point of hiring people who were previously incarcerated. She has built her restaurant in a way that allows her staff to flourish and thrive. It’s special to see a restaurant serving amazing food in a beautiful space while also doing good.’

Worth the wait: The Progress
‘This is the sister spot to a very popular restaurant called State Bird Provisions. The food is really delicious and served banquet-style. People often think it’s impossible to get in, but the trick is to show up and be willing to wait at the bar, then normally you can get a table within 30 minutes to an hour.’

For indulging: Rich Table
‘Rich Table is known for their incredible dried porcini donuts. Their entire menu is wonderful, but I tend to avoid the difficulty of reservations and stop in at the bar to have one of those as an indulgence.’

For brunch: Outerlands
This is one of San Francisco's go-to brunch spots that specializes in all kinds of carb-y deliciousness (though they have a pretty good veggie grain bowl, too). It has a gorgeous dark wood interior that makes it a dreamy oceanside spot.’

COFFEE
For a beautiful setting: Twentieth Century Café
‘It’s an unexpected spot that feels like it came out of the turn of the century, with a very quirky but beautiful aesthetic. Michelle Polzine who runs it has thought of every detail, from the design touches and the authenticity of the menu all the way to non-profits the café partners with. They also have this Russian honey tea cake that will absolutely knock you sideways.’

For coffee on-the-go: Equator
‘They’re a queer-run roaster that started in San Rafael but now has a few places in San Francisco. The Proof Lab Station spot on the route up to Mt. Tamalpais is my favorite. They have wonderful coffee and really cater to the adventurous surfing, hiking and biking crowd that comes through the area.’

DRINK IT IN
Go-to cocktail spot: True Laurel
‘Possibly my favorite bar in the city and go-to date spot is True Laurel. Deep in the Mission District, it was started by Nicolas Torres who originally did all the cocktails for one of the city’s top restaurants, Lazy Bear. I’m a very specific drink picker normally, but I will drink pretty much anything he has on the menu.’

For a decadent sip: The Riddler
‘This is a champagne bar in a beautiful spot that is entirely woman-run and woman-led. It’s a very powerful statement in the city, and one of the most decadent, luxurious spots in town.’

For drinks and a show: Oasis
‘For a great night out in the LGBTQ scene, I head here. It was a former bath house that was purchased by two drag aritsts in a response to the fact that a lot of the drag bars were closing as the city gentrified. They converted it into a bar and now host regular drag shows. I made it once for a 1980s-themed drag night and it’s still one of the highlights of my years in San Francisco.'

CULTURE HIT

For photography: Fraenkel Gallery
‘Historically, San Francisco hasn’t really been thought of as an arts city, but that’s been changing recently. The city’s biggest museum, SFMOMA, closed for three and a half years for a renovation, and with their reopening there was a huge influx of art into the city, which has been really exciting.

But through all of it, Fraenkel Gallery is a longstanding institution and my top personal favorite. Fraenkel was the gallery that helped to establish photography as a recognized art form in the United States. They show artists ranging from some of the biggest names in the photography world to exciting new contemporary artists like Wardell Milan and Richard T. Walker.’

For something unexpected: Minnesota Street Project
‘The complex that opened fairly recently in the Dogpatch district hosts multiple galleries that rotate exhibitions, so it’s a great place to drop by and catch something new.’

SHOPPING
For clothing: Pavilion
‘This spot opened up recently in the Mission and is run by local stylist and entrepreneur Mariko Yamasaki, who embodies a lot of contemporary New York and LA style that hasn't been catered to up here. She understood that there were people who wanted a curated selection of more high-end things — not just Patagonia vests — and has pulled a great selection of men’s and womenswear.’

For a decorative piece: Heath Ceramics
‘Heath Ceramics has been a powerhouse in the Bay Area for over a decade. They do everything from tiles and functional pieces to the most beautiful, artistic dishware. Their main shop in San Francisco is also their tile factory, so you can see the whole process while shopping.’

GET OUT OF THE CITY
A coastal escape: Point Reyes Station
‘I love to drive about an hour north to Point Reyes Station, a small beach town that’s kind of the ideal of what a small town should be. Check out the Point Reyes lighthouse, and in the town itself Cowgirl Creamery and Point Reyes Books are a must.’

For an arts getaway: Marin Headlands and Djerassi Resident Artists Program
‘Going up to the Marin Headlands is also lovely and heading to Rodeo Beach makes for a great day. Up in the Headlands you’ll find the Headlands Center for the Arts, where they converted a beautiful old historical military building into artist studios and galleries. They do a wonderful open house you can check out.

You have to keep an eye on the schedule to see when you can go, but one of my all-time things to go to is the Djerassi Resident Artists Program, which is an artist compound set on about 600 acres in the Santa Cruz mountains. They've taken more than 2,400 artists since their founding in 1979, and many of the artists there have embedded sculptures across the grounds and along hiking trails. They only open a few days a year to the public when you can tour the grounds and see these works in the stunning setting. But if you can make it, you’ll discover one of the most singularly magical places in the Bay Area.’