How to Travel the World for Free (And Win $4,000+ Worth of Prizes, Plus a Private Q&A)


4HWW trip around the world

If you have any interest in travel, then the next two minutes of reading are definitely worth your time.

It’s been too long since I’ve done a giveaway. I’ve been thinking about a trip to Australia or Montreal, so perhaps you’d like a getaway, too?  By that, I mean a vacation of epic proportions. I’ve partnered with StackSocial and Bootsnall to offer you a free ride around the globe.  Literally.  And there are tons of runner-up prizes (see below).

For those of you who really want to win, here’s a shortcut: Each time you share your unique link, which you get upon signing up, you receive another five entries. So spreading the word on Facebook and Twitter vastly improves your odds.

Click here to sign up. Share it well, and perhaps I’ll see you on the road!

Grand Prize: The Tim Ferriss Round-the-World Prize (worth $3,355.95)

1st Runner Up: The High-Flying DJI Drone Prize  (worth $1,034.95)

All hail the DJI Phantom 2–the king of the drones and a true aerial photography trailblazer. The 1st Runner Up will take home a brand new DJI along with 7 or our top-selling tech essentials!

2nd Runner Up: The Tech-Savvy Tastemaker Prize  (worth $355.95)

Score the 7 gadgets you need this fall–all designed by top innovators, all best sellers. Power up outside with a solar battery pack, power yourself around the world with one plug, and carry it all in the stylish FYL Bag.

Winner, Winner, Chicken Dinner…

To sign up, simply click here. And don’t forget, every time you share the page, your likelihood of winning increases.  Simple.

Hope to share a drink with you during your adventures.  One trip like this can change your life forever, so it’s worth taking 60 seconds to toss your hat in the ring.

Good luck and pura vida!

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Inside an “Anything Goes” Sex Club


“Those who are easily shocked should be shocked more often.” – Mae West

In this post, we’ll look two alternatives to monogamy: an “anything goes” sex club and living with three lovers at once.

It’s very graphic, definitely not suitable for work (NSFW), and guaranteed to offend most of you.

If you’re chomping at the bit to express mock outrage, please check this out instead. For the rest of you, I’m hoping the below is hilarious and somehow helpful.

Lifestyle design is, after all, about a lot more than work.

And if anything below shocks or appalls you, please ask yourself: why does this make me so uncomfortable? Dig into the discomfort. Looking inward before lashing outward is good for the world.

Now, on to the taboo.


As some of you know, I’ve been conflicted about monogamy for a long time. I love intimacy, but my biology craves novelty… Read More

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How to Never Check Luggage Again

Travel has many joys. Luggage is not one of them.

Travel has many joys. Luggage is not one of them.

This post will explore three options for never checking luggage again. Some of them are extreme; all of them are effective.

In my next post, I’ll detail what I (and some friends) pack in carry-on. Some are surprising and hilarious.

Given that I spend 100+ days of the year traveling, and that I’ve been to 40+ countries, I’ve tested just about everything.

Hauling a five-piece Samsonite set around the planet is hell on earth. I watched a friend do this up and down dozens of subway and hotel staircases in Europe for three weeks, and — while I laughed a lot, especially when he resorted to just dragging or throwing his bags down stairs — I’d like to save you the breakdown. Trip enjoyment is inversely proportionate to the amount of crap (re: distractions) you bring with you.

So, how to avoid checked luggage altogether?

We’ll cover three different options, in descending order of craziness. I promise that something in this post will work for every one of you, even if partially:

– Using “urban caching” for travel purposes
– Mailing instead of checking (and some Steve Jobs-ian quirks)
– Ultralight packing

Many of these suggestions have been given to me by readers over the years, so thank you!

I try and bring such gifts full circle by collecting hundreds of tips, testing them, and publishing the winners.

So here we go… Read More

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The Tim Ferriss Book Club Launches — Book #1: Vagabonding


The book Vagabonding traveled with me around the globe for 18 months.

This post is a dream come true.

Starting in college, I’ve fantasized about somehow driving fantastic but under-appreciated books into the limelight. I have a soft spot for out-of-print tomes and niche publications.

Flash forward, nearly 15 years later…

After three #1 bestsellers, I’ve finally pulled the trigger. For the last several months, I’ve been quietly buying audiobook and e-book rights to books that have changed my life, and producing audiobooks in professional studios.


This post launches the Tim Ferriss Book Club, and the first book is incredible: Vagabonding.

Why a Book Club?

There are several reasons… Read More

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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)

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How to Travel to Exotic, Expensive Cities on $50 a Day


(Photo: Marc P. Demoz)

OK, I’ve had a few short posts recently.

Now it’s time for my favorite: a post you will want to print out, refer to often, and take with you on adventures. In this case, we’ll explore budget travel that is luxury travel.

But what does that mean? It means that traveling inexpensively is a decision for creativity, not simply a decision against excessive spending. Throwing money at a trip means you are ordering from the normal, plain-vanilla menu (e.g. Marriott or Four Seasons hotels). This often means physically changing locations without changing your perspective or worldview at all.

In contrast, looking at how locals live — and find hidden gems — ensures you have amazing experiences that no guidebook can capture. This post is written by Matt Kepnes, better known as “Nomadic Matt.” He didn’t have his first overseas trip until age 23, and now he’s traveled to more than 70 countries.

His specialty is engineering first-class trips from economy-class budgets… Read More

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