An Ideal Day (or Weekend) in San Francisco – 16 Fun and Weird Activities


InsideHook SF Launch

San Francisco is my favorite city in the world, bar none.

I love NYC, I love Bali, and I love Buenos Aires, but SF is the place for me. And since I’ve been here for 10+ years, I get asked a lot: what should I do when I visit?

This post will highlight some of my favorite things.

Recently, I joined forces with InsideHook – the “essential lifestyle guide for adventurous and discerning men.” I’ll be their SF curator (and advisor), helping them find and share hidden gems in gadgets, food, outdoor adventure, and more. Subscribers get one hand-picked item per day via email. That’s it.

I encourage you to check it out here. At the very least, you’ll get an education in headlines, as their copywriters are amazing.

Now — onward!

Below is one of my ideal days in SF, planned out so everything is within close walking distance.

A Damn Fine Day

Wellness FX Blood Analysis
Activity: Blood-drawing and high-end diagnostics
Description: Visit one of Wellness FX’s labs for a blood drawing to produce an in-depth analysis of your state of health. Results offer a wide range of information, from cholesterol and hormone levels the to an analysis of your body’s electrolytes and vitamins.
Pricing: $29-$529+

SideWalk Juice
Activity: Smoothies, juice blends and more at 21st/Valencia.
Description: SideWalk provides made-to-order juices, smoothies & kombucha juice blends that are as delicious as they are beneficial to your physical and mental health.  My favorites?  The “Green Machine” and the “Jake Shields,” named after the local UFC fighter (“The strongest kale drink in existence!”).
Pricing: $4.25-$7.00

Street Art Tour
Activity: Walking tour of two alleyways with notable graffiti artwork with Dan Pan. We focused on the Mission district.
Description: Guided walking tour with Dan Pan, founder of 1AM Gallery’s new street-art app.  The app allows you to find nearby street art, as well as take pics and have users tell you the artist (very cool).  Try Clarion Alley as a starting point, which is run by an artists’ collective.
Pricing: The 1AM app is free.

InsideHook SF Launch
Mission Cliffs Climbing
Activity: Indoor rock climbing
Description: Indoor rock climbing at Mission Cliffs, a sprawling gym located at 2295 Harrison St.
Pricing: $20-$160

InsideHook SF Launch

Lunch at Salumeria
Activity: Lunch at Salumeria
Description: Salumeria is a 20th St. deli and larder that marries the culinary traditions of Old World Italy with the trend-hopping foodie culture of contemporary San Francisco.
Pricing: $6-$17

InsideHook SF Launch

Activity: Adult beverages with friends
Description: Enjoying social lubrication with new or old friends. A fine tradition as old as time. Some of my favorite spots include:
St. Vincent (Mission)
Hotel Biron (Downtown-ish, Hayes Valley)
Trick Dog (Mission; Disclosure: I’m an investor)
Bourbon and Branch (Tenderloin)
Pricing: Varies.

4 More Free Activities

Hawk Hill: where you can take a bike ride into our Cold War past.
Once upon a time, Fortress America dotted San Francisco’s hilltops with Nike missiles and radar outposts. Of course, those missiles were never fired — but you can still visit the rusted remnants of their vigilance if you bike up to the SF-87C radar outpost, the best-kept secret of the Marin Headlands coastline.

The Lands End Trail, where you’ll find the best maze in the Bay.
Truck up the Great Highway to stretch legs and strut your knowledge of the Sutro Baths. Hike up the Land’s End Trail from the ruins to the labyrinth at Eagle’s Point. It’s only a couple miles round trip, and damn fine panoramic views’ll be in serious supply.

California Cheese Trail: pairs well with Mission Cheese (below) or your vineyard of choice.
As an adult, your knowledge on cheese should surpass the realms of Lunchables and Easy Mac. Showing you the whey: the California Cheese Trail app from the folks at the Marin Agricultural Land Trust, available now for iPhone and Android. If you’re up for spending a few bucks on cheesy delights, visit Mission Cheese on Valencia.

The Bay Bridge’s long-awaited East Span.
The opening of the Bay Bridge’s new East Span has been years in the making, and now it’s officially open, welcoming pedestrians and cyclists of all stripes and offering exclusive access to Yerba Buena Island.

6 More Paid Activities

Vantigo: Tour beer breweries in a cherry-red VW Bus.
Indulge your nostalgia for simpler days with Vantigo, now offering tours of some of the Bay Area’s best microbreweries via a pristine ’71 VW Vanagon.
Pricing: $85 per person

Trumaker and Co.: Shirtmakers who come to you.
Restock your shirt library with Trumaker and Co., a custom shirtmaker with a highly mobile fleet of outfitters. It’s simple: you make an appointment, they send a tailor your way.
Pricing: from $98, free outfitter appointment

BoatboundBecause every man should own a boat…if only for a day.
Herein: your guide to using BoatBound, a new AirBnB-style boat rental service. SF Bay or Half Moon Bay?
Pricing: from $250 per day

Big Sur Roadhouse. The Big Sur getaway you’ve been looking for.
There’s a sprawling new Cajun restaurant in Big Sur. There are also some skinny-dip-friendly hot springs down the road. That gives you at least two good excuses to visit.
Pricing: from $50 per person

Mikkeller. It’s like a beer tour of Europe in a single bar.
The legend of Danish brewery Mikkeller has been growing across the pond for some time; they just opened their first North American alehouse in San Francisco.
Pricing: varies

Shelter Co.: Romantic private camping service with tent butlers.
Shelter Co. offers completely customized luxury camping experiences. You want tent butlers? They got tent butlers. You want a private island? They will rent you a private island.
Pricing: from $2000

Let’s Talk About This…

Want more activities, rare finds, and goodies? Sign up for InsideHook and let me know what you think. I’ll also choose one person who signs up for a 30-minute phone call with me.

Then what? How about you try my Pacific Northwest roadtrip from SF to Whistler? Damn, I love the Bay Area.

What’s your favorite city in the world, and what are your favorite 2-4 activities?


If you’ve ever fantasized about taking time off to globe-trot, I would highly recommend Rolf Pott’s Vagabonding. It is one of only two books I took with me when I traveled the world for 18 months. Outside Magazine founding editor Tim Cahill calls Vagabonding “the most sensible book of travel related advice ever written.”

I recently partnered with Rolf to release the exclusive audiobook for Vagabonding. For more on this incredible book, click here

Related Posts:
How to Live Like a Rock Star in Buenos Aires
How to Hack Tokyo for Less Than NYC
How to Travel Through 20+ Countries with Free Room and Board
How to Travel to Exotic, Expensive Cities on $50 a Day (e.g. Paris, Hong Kong)

Posted on: September 7, 2013.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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94 comments on “An Ideal Day (or Weekend) in San Francisco – 16 Fun and Weird Activities

      • I’m brand new to all you do. I found you thru my desire to get out of a 60 hour plus work week as a truck driver. I have 5 lucrative ideas to get me out of driving but little time to do physical work. Two of the ideas are in motion after listening to the 4 hour work week. One of the ideas got me into the small business class at Oswego State this weekend but they’re saying I’m in need of 100,000 at least for start up. It’s going to be like only a different service no one has done yet. 3 successful people I have shared with are excited for me and believe I need to keep it quiet. This is going to be huge. Thanks for the inspiration. I am telling everyone I know to check your stuff out. I give drum lessons too btw if you want to add drumming to your list of things you can do. Have an amazing night.


  1. Tim, I’m inspired to visit SF, especially as it gets cold here in Toronto. What time of year would you advise visiting?

    My favorite city is Krakow, Poland. Just walking around the old market square and enjoying a cold beer does it for me.


  2. Just singed up for the site. It looks really clean, and I love the way the logo is designed. The Speak Easy Idea is really interesting as well, I think I’m going to try and find my way in.


  3. That gets more and more excited to visit SF.
    You once mentioned “House of Air” and how you recommend it to SF visitors! And definitely expected to see it on this list…have you forgotten it? or have you lost interest?


  4. My favourite city is Vancouver, BC.
    Where I was born and raised.
    (I did live in Whistler for 10 years – but the city called me back).

    Favourite things to do:

    1) Hike up the trail “beside” the Grouse Grind – Called the BCMC trail, and then have a well deserved burger and beer at the top of Grouse Mountain overlooking the city.

    2) Brunch at Fable. Only on Saturday and Sunday. Great local restaurant. On 4th Street, close to Burrard.

    3) Walking the trails in and around Spanish Banks and the forest just above it.

    4) Tinctured-infused drinks at the Keefer Bar. Gastown area. The owner and head bartender (a lovely lady I might add) makes tinctures from various Chinese herbs – the decor and bar is AMAZING!


  5. It’s funny, I’ve lived in a few places (Melbourne, Chicago, and Santa Monica) and I couldn’t rate any city as my favorite. Is it a city that make the memories or the people you invest your time with?

    That being said, I’ll share 3 amazing things to do in New York City:
    – Go to IBM’s THINK Exhibit. I was profoundly inspired by this Exhibit and realized I’d rather solve real problems with technology than simply trade my time for money/startup fame. Exhibit info:
    – Go to any of the comedy clubs. FYI: Most comedy clubs advertise each night as a live taping of a Comedy Central special, it’s a lie, but still a lot of fun.
    – Eat a meal at SkyLight diner (


  6. My Favorite city is either Cuenca,Ecuador or as of July 2013…San Fransico. I went with the fam on a road trip starting from Ventura and must say San Fran is an amazing place. For those just driving through check out Haight-Ashbury (birth of hippie movement) to people watch, go to the docks to watch sea lions and drink Anchor Steam beer, or head north to wine country and check out the Gundlauch Bundschu Winery. All a great time.


  7. InsideHook is a great idea, I will definitely be signing up. I had never visited SF until 8 months ago when I joined AmeriCorps and flew out to Sacramento to start my service. When I went to SF for the first time I fell in love. I was only there for a weekend, but I had the time of my life and I can’t wait to go back, or hopefully even move there.

    After visiting NYC, DC, Philly, Boston, San Antonio, Billings, SF, and many other cities, I can definitely say that SF is my favorite. I plan on going overseas during 2014, so maybe that will change. However, I live near DC and my favorite things to do there are bowl at Luck Strike Lanes, go to a Capitals or Nationals game, visit the Smithsonian museums, and watch street performers play music on buckets, shopping carts, etc.


  8. Perfect timing on this post since I am in San Francisco for the weekend! Thanks Tim, both for this and for everything you do. You’ve made my life consistently better since 2008 when I read your “Live like a rockstar in Buenos Aires” post. I went to BA shortly thereafter for a month and the trip lived up to its promise. My work life was transformed by your first book, I’m down 35 pounds thanks to your second book and I am teaching my son to cook with your third book. You rock!


  9. A favorite SF activity of mine is walking through the Ferry Building and treating it as a “tasting menu” by purchasing one item per shop. The wine bar there is cool enough to let you bring in foods from the various purveyors, and their wine by the glass list is killer.


  10. Inside Hook is ok. The articles don’t win me over with their writing and the ads everywhere trip me out.

    My favorite city is Patong in Phuket. Riding motorbikes, swimming in the beautiful talay(ocean in Thai), hanging with locals and learning Thai, sanuk mak mak.