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.

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

  1. Signed up!

    Loved the post and the website. It has a lot to do with our startup as we have several local experts planning itineraries for travelers around the world. So, I’ll look more in detail to get some inspiration ;)



  2. I signed up hoping for the phone call, but if not, I’m hoping this comment will inspire to write a post :-)

    I know you’re not an MD, but I love your beautiful mind and highly respect your opinion so, I would love to know your thoughts on debatable and contradicting medicine/diet. I’m one of those guys with screaming high cholesterol, but I’ve always been pretty healthy and fit. I find conflicting info about statins & cholesterol. I have such a hard time trusting our profit based American medical system that I just don’t know what to believe!

    How do you make such decisions for yourself? What country or what medical centers do you trust? I hope you write about this because I trust your experimentation (on yourself :-) and you scientific search for truth.



    • Oh and btw, you’ve inspired me to follow my life long dream and go to Thailand the whole month of February to train Muay Thai there and visit the country side. Thought you should know!


  3. Hi Tim, thanks for sharing this with us.

    My favorite city is Toulouse (France)

    The city where my husband and I settled 10 years ago for a brand new life after quitting Paris for a better and more quiet life…

    You want to know the reasons why I ‘love’ Toulouse?

    – Whenever I miss Paris, I just have to enter a shopping mall or any market place and I’m pretty sure to find someone with a grumpy face which reminds me of the parisians:)
    OR I just have to jump in my car and get caught in a huge traffic jam almost similar to the ones in Paris, isn’t that magic!
    – For the last 10 years I succeeded not stepping in a dog poop while walking in the city center, whick is kind of an achievement, YESS!
    – I’m part of the few heroes who did find a job which is not in Airbus or aircraft industries

    More seriously, as I write this down, I realise I’m being very unfair: Toulouse has a lot more to offer…
    – Great architecture with pink brick buildings, nice monuments such as the Basilique Saint-Sernin really worth visiting
    – Nice restaurants such as ‘Chez Emile’ to eat a cassoulet (white beans with saussages, specialty form the south west of France)
    or L’Empereur de Huey (Great Vietnamese restaurant)
    – Nice weather
    – Great base to visit the Pyrenees mountains or the mediterranean sea (just 1 hour drive from the city)
    And first and foremost, this is the town where I had a chance to be a mother and raise my daughter, one of the most beautiful experience of my life.

    One of my favourite spot is “Place Saint-Georges”, very cute little place, where you can seat and relax at a café’s terrasse just next to the kids playground (your kids will have fun too;)
    or stroll by the Garonne river and enjoy the view,
    or even dance salsa, out on the “quais de la Daurade” on sundays afternoons during summer time.

    Take care;)


    • Cecile,
      you’re totally right! I’m a Toulousain, borned and living in Toulouse. It is fun to see someone on this blog saying Toulouse is her favorite city, love the Internet for that :)
      You’ve just missed one point about Toulouse, it’s the fact that it is a very lively city, with always people outside.
      But I love SF too, it’s a peaceful and great city, with lovely neighborhoods.


      • Hi Al,

        Nice to find a real ‘toulousain’ at Tim’s place too;)

        By the way: thank you Tim for inviting us to share on your blog: it feels like we’re sitting on your livingroom’s coach right now – sipping a delicious mojito (my favourite dring on earth) – just to illustrate how cool it is..:)

        Anyway, Toulouse is great and there are so many places great too. I think I actually could live anywhere in the world as long as I have my family with me.
        The thing is, I usually associate a place with the emotions I felt there. For instance I have such an amazing souvenir of watching the sea lions liying on the beach when driving from San Francisco to LA. That was maybe 15 years ago and I still have this image in my mind as if it was yesterday. Nature is so wonderfull.



  4. Tim,

    I’ve been a fan of inside hook for awhile. As a single male in SF, the Sept 6th email Where to Take a Her decision chart was awesome. Will definitely get a lot of use from that email, whether I’m in the dog house or just meet someone new!

    Glad you’re an advisor, definitely will be a long time subscriber.


  5. I got an email about the Contango briefcase from InsideHook immediately after signing up- It looks like it is well made and $75 off is pretty enticing as well- seems like a great service- eager to see more e-mails. I am looking forward to your call Tim- I spent four years in the Air Force in the Bay area and miss many aspects of the lifestyle out there- I certainly miss the skiing, Yosemite, Wine Country, ridiculously beautiful ocean vistas, Redwoods….the list goes on. San Francisco is a gem. Thanks for the scoop Tim.


  6. I have never been to San Francisco my entire life but the activities presented in this post are the things that I love doing in my own home town and basically still the same things I’d love to do when I visit a new place like SF.

    In the event that I’ll be in San Francisco and if I have limited budget and time the top three(3) places I’d visit are: Boatbound, because I totally agree that every man should be given a chance to the luxury of owning a boat even just once; Mikkeller, because I’ve been drinking American beer all my ‘grown-up’ life and only got a very few occasions where I tasted European beer; and The Lands End Trail, because it’s free and I think it’s fun to go there with my partner.

    I am open to invitations too so long as beer is free!


  7. My two favorite cities in the world are London and NYC. I currently live in Kingston, Jamaica though, and there’s a hell of a lot to do in Kingston that people don’t know about:

    Like :
    – two of the best beaches in Jamaica – Lime Cay and Maiden Cay
    – The nightly parties
    -Hollywell National Park(outside of Kingston but only an hours drive)
    -Blue Mountain Trek
    -The parties at the university of the west indies

    If you want to get out of kingston and see awesome beaches and scenery forget Negril or Montego Bay…go to Portland and get a villa or stay at Canopy…Portland is easily the most beautiful Parish and has the lowest crime rate in all of Jamaica..a great combination. Portland has Castles, Islands owned by Errol Flynn, A real Dutchess of Austria as a resident, and easily the best scenery in the Caribbean.

    Hope that was helpful.


  8. I seriously got this in my mailbox as I was doing an itinerary last week to SF from Miami, great timing, man. Just got here yesterday with my boyfriend, huge fans here (mostly me, the bf is jelly hehe) I really hope we run into you at one of these cool places!! Also, bf signed up for InsideHook, any thoughts on adding Miami to it?


  9. Hey Tim:

    Well, you live in my favorite city in the world. I’ve not found anywhere that has trumped the SF Bay area. Here are my top four things to do:

    1. Head south to Monterrey and enjoy the quite coastal life and to see what’s around the next bend on PCH.

    2. Take my son on the Felton Railroad just a stone’s throw north of Santa Cruz after spending a sunny day on the boardwalk.

    3. Eat at Golden Era Vegetarian Restaurant (Plug Intended) on O’Farrell street.

    4. Walk beyond the tourist masses at the entrance of Muir Woods to enjoy God’s cathedral. Absolutely no place like it on earth.

    Your blessed to live and enjoy life in a truly excellent location.


  10. Hey, great post. I love activity tipps from locals and next time when I will be in San Francisco I will definitly try a few things of your list. Last year I did only the tourism stuff, which are really nice too, like riding the bridge, going to muir wood and many more. But the best time will be living and doing like a local


  11. Hi Timothy,

    I just signed up for InsideHook, and I think that the site looks awesome.

    Now, when can we have those 30 minutes together? ;-)

    This is Anto from India, and I think, your ‘The Four Hour WorkWeek’ book is way more AWESOME than the above site.

    Thanks a lot for your ‘The Four Hour WorkWeek’ book,


  12. San Francisco is incredibly dirty. Wasn’t expecting that at all, its proximity to other things (coast, mountains, etc) is the only real selling point. I much prefer visiting Chicago, which is cleaner, has entirely open water fronts, and is on par with NYC for culture and food.


  13. Love San Francisco!
    Favorite SF meals: garlic crab and garlic noodles at Crustacean. And the market at the Ferry Building…and of course, The Sliding Door, and Brother’s Korean BBQ…so many!
    Favorite cities: San Francisco, New York, Paris, Hong Kong, Sydney, etc…..
    Fave places: New Zealand south island ski slopes, Whistler, Mammoth, Hawaii big island beaches…


  14. Better than any of those: Surfing!

    It’s free, creates a dopamine surge like no other, and it just so happens that Ocean Beach has had it’s best winter season since God knows when.

    Let me teach you to surf! I’m a former surf instructor (I went to UCSD as an undergrad), currently employed as a forensic psychologist. My research on surfers – tough life, I know – has been published in peer-reviewed sports psychology journals and featured in Surfer magazine.

    Hit me up; we’ll have a blast, and trust me, your life will take a different trajectory post-stoke.


  15. my favorite cities in ascending order are:

    favorite things to do in Miami:
    sit on the beach
    stare at the ocean
    have an adult beverage