The worse the road, the better the destination: 10 travel secrets I've learned from backpacking around the world

Learn about the power of ferries, sculpture gardens, shoulder season, and why agendas are for suckers. Also: Apology mad lib, how to be a good boyfriend, breaking up with Google, & more.

This is the Rubesletter from Matt Ruby, comedianwriter, and the creator of Vooza. Sign up to get it in your inbox weekly. 

The end of lockdown is in sight (right!?). That means we’re on the eve of a massive travel boom. And that’s got me reminiscing about my past journeys (I’ve spent 20+ years taking backpacking trips around the world) and lessons I’ve learned along the way. Here’s travel advice gleaned from roaming the world...

How to travel

Shoulder season is the time to go
Peak season is for suckers. You want May, not August. It’s cheaper, it’s not as hot, and you don’t have to compete with tour buses. (It’s a life lesson too; when the mob zigs, you should zag.) The bigger point: Don’t give crowds and lines much credit. People who can’t think for themselves actually crave waiting in line; it offers social proof they’re not making a bad decision. Doing what everyone else is doing minimizes risk. Unfortunately, living this way results in being constantly surrounded by a bunch of other mooks who can’t think for themselves either. “We need to see the Mona Lisa.” Fine, you can wait two hours to catch a glimpse of her smile from across the street – or you can skip it, go down another hallway, and see another piece of art up close that’s just as amazing, without getting swallowed up by a bunch of selfie stick suckers.

Don’t plan too much
Backpacking isn’t about your luggage choice, it’s about an anti-itinerary attitude. You buy a ticket, arrive, find a place to stay for the night, and figure it out from there. The only real plan is to keep updating and adjusting your plan based on real-time information. Does that Aussie couple in your hostel know about a waterfall/cooking class/monastery in the north that’s amazing? Then that’s where you’re headed next. Take this approach and you realize the silliest thing is to attempt to plan an entire trip agenda from home, the place where you have the least information and are most likely to get ripped off.

Go to single artist museums and outdoor sculpture gardens 
When a museum is devoted to one artist, you get to see their evolution instead of some shuffled playlist of various artists. You get a deep dive into one person’s entire discography when you go to the Van Gogh museum in Amsterdam, the Chagall museum in Nice, or the Museu Picasso in Barcelona. You see how their artwork evolved over their entire lives and that context is illuminating. Also, go to outdoor sculpture museums in pretty places whenever you can. It’s a good excuse for a day trip, a scenic view along the way, some cool art, and a reason to stroll outdoors. My faves: Fondation Maeght in southeast France, Louisiana Museum of Modern Art outside Copenhagen, and Storm King outside NYC.

Get off your phone
Old man alert: Lots of my traveling was before smartphones. So instead of checking Google Maps, I ripped out pages from a Lonely Planet guidebook to orient myself. There were no cheapo airlines like Ryanair so I slept on overnight trains which took forever to reach their destination. There was no Airbnb; the ferry landed and a bunch of old ladies waited on the dock holding laminated photos of the apartment they had for rent and then guided you there. You can technologize your way around a lot of hassles nowadays, but when you stick to a “TripAdvisor Top 10” mindset, you’re likely to have a cookie cutter experience. Putting the phone away leads to more randomness, intriguing interactions, and long cuts. These days, I carry a phone when traveling, but I tend to leave it in airplane mode. You save money on international fees, maps still work in airplane mode if you preload ‘em, and you can always find a café with wifi if you really need to get online.

Go one stop further than everyone else
Those extra few hours are usually worth it. Isla Holbox is a real pain to reach; you’ve got to fly to Cancun, then drive for hours (beware of “tolls” enforced by cops/bandits along the way), take a ferry, and get picked up by a golf cart since there are no cars on the island. But then you realize why you put up with all that: secluded beaches, dusty cabanas, an old town that looks like a movie set, and tiny restaurants on the beach serving fish caught an hour ago. Everyone hits Machu Picchu but how many take the extra travel time to reach the moonscape that is the Uyuni salt dessert in Bolivia? There’s no day trip possible to the Ngorongoro crater in Tanzania; but I’ll never forget seeing lions play with their cubs there as the sun rose in the background. As my friend Debra put it on that trip: “The worse the road, the better the destination.” Related: If you’re ever choosing between a place that requires a ferry and one that doesn’t, choose the destination that involves a ferry. Just reframe the sailing part of the journey in your mind: A “ferry” sounds lame, but a “boat trip” sounds like the sort of thing people would pay extra to experience.

Go wild  
Tolstoy wrote, "All happy families are alike; each unhappy family is unhappy in its own way." The travel version: All cities are alike; each wild place is wild in its own way. Cities are fueled by commerce, but wild places are fueled by planetary forces. And if you’re already a big city resident, you probably need a dose of trees/mountains/oceans the most. In Argentina, I enjoyed Buenos Aires, but it didn’t strike me as wildly dissimilar to other big cities I’ve visited. But then I travelled south to Patagonia, where the Andes, glaciers, penguins, gauchos, and rancherias collide. It’s only habitable for a few months out of the year so you sense you’re in a special, mystical place. Buenos Aires is a blur, but I still remember the creaks and moans of the glaciers, the smell of the mountains, and the taste of the beef in Patagonia. 

Enjoy your liberation from lawyers
80% of the world's lawyers live in the United States. We marinate in risk management, waivers, and weird dudes on highway billboards. It’s infantilizing. Elsewhere, you assume your own risk. I crawled through narrow tunnels to reach an underground city in central Turkey. I swam in all kinds of weird caves and waterfalls. In Bolivia, I took a bike ride down “the world’s most dangerous road.” (It’s a mountain descent down a narrow, cliffside road. A car plunges over the cliff every two weeks or so and, a few days before our trip, a cyclist went over the edge.) You can decide for yourself how much you want to stay between the lines, but it’s refreshing to at least be given a choice.

See like a photographer
When I travel, I shoot lots of photos. I get some cool shots, but I’ve come to realize the shooting mindset is what’s really valuable. It changes the way I see things and interact with my environment. I notice details in a different way; walking down the street becomes a full sensory experience. I go out at dawn/dusk, I get a bird’s eye view, I venture to odd parts of town. I stare at shadows, textures, and buildings longer. Carrying a camera helps me see more. Plus, it’s nice to have actual photos, the kind you can collect later in a book. Yes, go analog and print a book; no one wants to see photos on your phone. Plus, you’ll keep that book for the rest of your life. (Good luck accessing any of your digital photos 30 years from now.) Also: Don’t take the same photo everyone else is taking. You can just find that one online. Find a weird angle, zoom in too tight, or do something else that creates a photo only you could have taken.

Turn up your BS detector
In Belgium, there’s a site popular among tourists called Manneken Pis. It’s a statue of a little boy pissing in a fountain. There’s nothing pretty or interesting about it, yet people come from all over the world to take pictures there because, well, it’s “the thing to do.” Sometimes there’s no way to know until you get there. But sometimes you can read a description and say to yourself, “It’s a statue of a little boy pissing in a fountain? No thanks.” Another time, I went to a popular “tourist destination” in southern Vietnam. It was the site of a wartime bombing during the sixties. We drove for hours to get there and when we arrived, we found a large field with a slight indent in it. That’s it. Well, played Vietnam. I actually admired the collusion required to pull off that one. And hey, when your country is the one that did the bombing, it feels like understandable payback. In addition to healthy skepticism, avoid attracting drama into your world when you travel. Keep your voice down, don’t wear flashy stuff, walk with intention, etc. Most places aren’t that dangerous unless you act like a mark. Don’t be a fool and foolish things won’t happen to you.

The meals you remember are the cheap ones
When the clubs let out in southern Turkey, there’s an interesting late night food option: the baked potato vendor. It’s a guy on a bike that has an oven on the back. It’s filled with piping hot baked potatoes. He puts out 15 different condiments (sour cream, cheese, spicy peppers, etc.) and you top your tot however you please. It’s brilliant and I don’t understand why I’ve never seen this anywhere else. Also, the pintxos in Basque country (northern Spain) were the best bar food I’ve ever had in my life. They know what to charge by counting the toothpicks on your plate. Also, fresh bread and cheese is a delicious, portable, cheap way to get by on long train rides. And while I’m preaching cheapness: The biggest waste of money in traveling is hotel rooms. You’re barely going to be there anyway. You just need a roof and a bed. Save the money you’d use to stay somewhere fancy and treat yourself to a few extra days on the road instead.

Notice how it feels to be the outsider
Traveling loose like this frequently involves relying on the kindness of strangers. You need directions, suggestions, translations, and a decent exchange rate. People don’t understand you and you’re no longer the center of the universe. It’s a real ego check to depend on others to that degree. In fact, it can be downright humbling. But this is not weakness, it is a muscle. It shifts your perspective (especially if you’re privileged/straight/white/male/American). You start to look out for fellow travelers, even when you’re back home. It makes you patient when someone is confused and helpful when someone is lost. You’re never the same after you’ve been a stranger in a strange land. You go home, but you remain, forever, slightly strange. And that’s a good thing.



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-Matt Levy

How to be a good boyfriend

Here’s a bit on love in the time of Instagram:

This joke featured on my “Feels Like Matt Ruby” special. Watch it free on YouTube or stream the album.

Mad Lib to appease mad libs

The groveling apology is now one of the main forms of discourse on social media. At this rate, we’re all gonna wind up in the cancel culture crosshairs eventually so here’s a handy fill-in-the-blank form to use when you inevitably screw up.

Apology Mad Lib

I want to [apologize/grovel/beg for forgiveness] to [howling co-workers/strangers on Twitter/anyone who’s ever been offended] for [trivial incident/offensive joke/saying something unpopular]. And to the many [offended group/victims/lookie-loos who just love drama] who [went to HR/posted nasty things on social media/tattletaled to the principal]: your trauma is [holy/sacred/my guiding light from here on out] and my behavior is [awful/horrible/I genuflect at your feet and now will wash them].

My conduct around [mostly legitimate issue that may or may not be being hijacked for Likes on social media] was [ignorant/evil/like Darth Vader meets Lex Luthor meets Martin Shkreli]. I did not pay enough attention to the [aggrieved group, powerless victims, the outrage industrial complex] at [organization/Slack channel/mob outside my door with pitchforks] and I should have [acted like a hero/led a revolution/tattooed their faces on my body like a Ben Affleck back phoenix as a sign of my dedication to their righteous cause].

For this, I feel [filled with regret/like I belong in a dungeon/actually I’m already slapping myself in the face right now]. I apologize to [everyone involved/my parents for being born/everyone reading this schlock]. I’m [humbled/grateful/secretly enjoying the ongoing punishment because I’m a bit of a masochist] by how much I still have to [learn/grow/evolve from a dirty frog into a glowing prince and I don’t mean that in way that is frogist or dirtist and I recognize the royal family’s hierarchy is actually a manifestation of the patriarchy] and I am committed to doing [better/the work/whatever it takes to never have to write one of these things again].

Hope that helps!

Related: How people who create cancel culture are like people who create climate change (according to Rob Henderson). They both feel "instant convenience and gratification are not worth the looming possibility of future danger."


I'm waiting for the vaccine to come out in gummy form. 🌀 I don’t mind masks. People used to tell me I have resting bitch face. But now they just tell me I have resting bitch eyes.

Tech’d up
"Let's see how all my friends filled with hatred are doing." -Me when I open up Twitter 🌀 Startups sell passion to employees the way Instagram models sell butts to their followers. 🌀 I just declared email bankruptcy. Whoops. No. I just declared bankruptcy via email. 🌀 Getting really into fintech (got a dolphin tracking device). 🌀 Salesforce is p*rn for people who hang out in LinkedIn all day. 🌀 The 5th Stage of Cancellation: Social media starts claiming, "I never liked his stuff in the first place." 🌀 We should be making a bigger deal of this Mars Perseverance landing. It is the opposite of politics. It's proof we can still do big things if we let scientists and smart people do science and smart people things.

Politicked off
I guess you could say Young Pharoah got "passed over" by CPAC. 🌀 The better a politician is at social media, the worse they are at compromising. And that's why the government never gets anything done; it's bad for Likes. We've set up a system where pols do way better dunking on their enemies than negotiating with them. 🌀 I thought big money, corporations, & the 1% controlled politics. So can't they reel in the wacko fringe of the GOP in order to keep getting their tax cuts and to avoid regulation? And if they can't, doesn't that mean the whole thing about the 1% controlling the country is wrong? 🌀 Irresistible force paradox: "What happens when an unstoppable force meets an immovable object?" The American paradox: "What happens when short term attention spans meet infinite scroll?" 🌀 One's real name is Robert yet he wants to be called Beto. And the other's real name is Rafael yet he wants to be called Ted. Kinda tells you everything you need to know about both of 'em. 🌀 "Witch Hunt!" Because, as we all know, if Donald Trump had lived in colonial times, he would have sided with the women accused of being witches and defended them against the mob of angry men out to get them.


1) Great Brody Stevens standup story from John Roy. It's also a lesson about how you sometimes need to abandon your material as a comic. Maslow's hierarchy of comedy: First, you gotta get the room to pay attention and come together. If you ain't got that, your material won't go anywhere.

2) Stevie! Damn, talk about coming in hot.

My fave genre of live performance vids is funky/rocking bands going HARD in front of 1970s European audiences who just sit there stonefaced and seem to have no idea how to react to what they’re watching.

Best runs of the past 50 years: Stevie Wonder in the 70's, Michael Jordan in the 90's, and Steve Jobs in the 00's.

3) Smart idea alert: Start with your best, not your latest. We’re too married too sorting by date, which can be bad for newbies. This "Here's where to start!" graphic for ‎Why Won't You Date Me? podcast with Nicole Byer offers a better way. Unless your latest is always your best starting point, give ‘em your hookiest hooks.

4) “What does a lesbian bring on a second date?” “A U-Haul.” Pretty cool that Lea DeLaria did this joke decades ago on Arsenio and "U-haul lesbian" is now a common term that’s still referred to decades later. Mentioned it on Twitter and Lea replied:

I did do the joke on Arsenio but I actually wrote that joke for a Show I did in 1989 called Lesbo-A-Gogo. Which ran in PTown that entire summer. The joke was so popular that when it became time for me to do my winter tour it beat me to the west coast.

A joke that travels faster than the comic pre-internet musta really struck a nerve.

5) Good writing is pointing out (from Oliver Burkeman):

As Steven Pinker notes in his book The Sense of Style, writing is cognitively unnatural: it's such a new way of communicating, on the timescale of human evolution, that it's little wonder we struggle…Pinker suggests approaching writing as if you were pointing something in the environment out to another person – something that she would notice for herself, if only she knew where to look. Imagine directing someone's gaze across a valley, to a specific house on the other side. "You should pretend," writes Pinker, "that you, the writer, see something in the world that's interesting, and that you're directing the attention of your reader to that thing." He calls this the "joint attention" strategy.

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About the Rubesletter: Weekly musings from a standup comedian and startup veteran. If you like my comedy or writing; if you dig tech, politics, art, wellness, & pop culture; if you enjoy smart/nuanced takes & hate BS; if you’d like me to turn you on to other people making cool stuff: Sign up.

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My latest standup special is free on YouTube. And you can stream my standup albums “Feels Like Matt Ruby” and “Hot Flashes” too.