The Top Twenty Apps and Sites to Find Fun, Romance and Adventure on the Road and at Home

Looking for a little fun and adventure in your life? 

Tired of the same old routine of falling asleep in front of the TV after heating up leftovers in the microwave?

Lucky you. It’s a big, exciting world out there.

And guess what?

If you’re alive today, you’re the luckiest 1% of 1% of people who’ve ever lived.


Maybe it doesn’t feel like that if you spend all your time watching the news ( a toxic wasteland of emotional manipulation ) or things aren’t going perfectly in your life ( nobody’s ever is ) but it’s true. Our parents, grandparents and great grandparents experienced war, tragedy and heart ache on a scale that’s nearly impossible to imagine today.

But now is a renaissance unlike any other time in history. We have more access to fun and adventure than ever before and maybe ever again.

All you have to do is open your eyes, control your fear, uncertainty and doubt and take a wild leap into the unknown.

Culture. Arts. Food. Fun. Travel. Romance. Adventure.

It’s all there, waiting for you.

Whether you’re broke, doing all right, or straight flush with cash, there’s something out there for you to love.

And with the Internet, smart phones and a bazillion apps, it’s easy to find fun and adventure.

Maybe you’re just tired of Netflixing and chilling or going to the same bars with the same friends? Or maybe you’ve got a big vacation planned and you want to do more then get drunk or just sit on the beach wondering about all the work piling up back home?

Or you’ve taken a bigger risk and started digital nomading? Or you just quit your job and decided to head to India or Bali or Hong Kong to find yourself?

Or maybe you’re just trying to figure out how to change your life and have more fun?

I’m here to help.

First we’ll talk about the right mindset you need for adventure and then we’ll talk about how to find those adventures.

The First Step: Change Your Mind, Change Your Life

If you’re ready to start experiencing life, the first thing you have to do is change your mind and the way you look at life.

You can’t keep doing the same things you’ve always done. The definition of insanity is doing the same things over and over and expecting different results.

You have to do things you’ve never done before, step out of your comfort zone and take a risk. 


That means you’ll experience fear. But strangely enough, fear is nothing to be afraid of, it’s exactly the opposite. It’s more like a guiding light to doing something. The more afraid you are the more you should leap right in and do it. Use your fear like a guiding light.

Now, of course, this is not true in everything. I’m talking about taking a trip, going on a date, eating something you’d never think to eat before now or jumping out of an airplane (with a parachute). I’m not talking about robbing a liquor store or having sex with a stranger without protection, you psychopath. There’s proper risk taking and just being crazy. Don’t be crazy. This is about fun, not killing yourself.

The first operation is always “do not die.” Operation do-not-die-tonight is always your number one focus.

After that all bets are off.

Step Two: Release Expectations

Look, not everything is going to work out.

One of the hardest lessons in life, and one I’m still trying to learn, is you can’t control everything.

You’re going to go on a bike tour of Hong Kong, only to find that you didn’t vibe with the person leading it or it started raining half way through. You’ll go on a date where you can’t stand the person across the table.

You can’t control the outcome. All you can do is go do something new with an open mind. And when it sucks, go home early after giving it a fair shot.

It’s easy to get depressed after something goes wrong. You’ll want to give up and say that doing cool shit is only for people cooler than you but that’s not true. Feel the sadness of it and come back fighting the next day. Get back on that horse and ride again.

Then one day you’ll get on a paraglider and wonder where it’s been your whole life and why you weren’t doing it years ago!

Step Three: Learn Your Lessons

This is the hardest part.

When things go wrong, or you get stuck in an airport in Timbuktu, or your iPhone gets stolen, you’ve got to learn from it as fast as possible and get back into the game.

It’s easy to give up when things go wrong. Every day is a new day and you get no credit for the things you did yesterday. You can wake up on top of the world one day, only to wonder how to drag yourself out of bed the next.

I’ve been there. I’m still there some days.

The last two years were the best and worst years of my life. I got kind of famous and kind of rich and then very poor again. I struck out for a life of adventure, traveled the world, gave talks before big audiences and small, lived, laughed, cried, loved and lost love. I experienced the highest highs and the lowest lows. I hiked in mountains, went to the world’s greatest and smallest museums, ate amazing street food, met incredible people, and lost myself and found myself in cities near and far.

I spent days filled with joy and other days curled into a ball crying. I lost friends and made new ones, watched people close to me get sick and crash out of their life, had other friends die or get sick or lose their way, and I lost several ladies I hoped to be with until my dying days.

And none of this will stop me.

All along the way, I’ve learned there is no joy without pain. One simply cannot exist without the other. Not everything you do will lead to triumph. Tragedy and triumph are both imposters. As Kipling says, treat both imposters just the same.

When things go wrong, learn from it. Do whatever you have to do. Talk to a therapist, reassess, workout, read books, grow and change. 

Step Four: Finding Adventure

All right, you set your life on fire to travel the world, or maybe you finally took that three weeks of vacation instead of skipping it this year and you’ve touched down in a new city. Or maybe you’ve just got a hot date in your home town and you don’t know what to do next? Don’t sit in that house and worry!

All the answers await you on this magical thing we call the Internet. It’s time to start downloading some apps!

There’s an app for everything!

So let’s take a look the killer apps for awesome experiences.

A Room of One’s Own

First of all you’re going to want to find a place to stay so let’s get on it.

Everyone knows Airbnb and Hotel Tonight so I’m not going to waste digital ink telling you about them. If you don’t have either of those apps installed and ready to go, then you should start there but if you’re looking for an alternative to peer to peer housing or hotels then co-living might the adventure you’re looking for right now. 

Co-living spaces give you a private bedroom and shared common areas, like an industrial kitchen, a co-working space and often times awesome amenities like a meditation room or a pool. It’s a great way to meet new people and still have privacy.

Co-living communities are popping up all over the world. They’re like an upscale twist on the old hippie communes of the 1960s or the hostels you stayed in as a youth, but so much better than both of those things. Some co-living places are super upscale and some are anything but. The lowest priced ones have shared rooms, with bunk beds. If you’re young and don’t much care about personal privacy those might be the ones for you. But if you’re a little older you’ll want to level up to the ones that have private bedrooms and private bathrooms.

A lot of co-living places cater only to longer term stays, like two or three months so they’re not awesome for people on a two week vacation but some of them allow for much shorter stays of only a few days or a few weeks, like Roam, which has places in Miami, Bali, Tokyo, and more.

Most of these communities are old mansions or boutique hotels with lavish gated communities. There’s an emphasis on communities in a lot of these spaces, with people getting together to exchange ideas or just do yoga or go to a club together. It’s a bit like a living friendship and dating app. You can run into people in the kitchen and strike up a conversation or just keep to yourself if you’re not feeling particularly social. 

I found myself sharing a bottle of whiskey with folks and discussing the meaning of life and other times I would happen into the kitchen when some excellent cook was doing his or her thing and she was more than happy to share. If you’re cool and chill and give back to the community people will give back to you.

More and more of these places are coming online. But be careful. Sometimes websites have nothing but an architectural drawing or a planned community that is not open yet. As of yet there is no central screening app for finding all of these places and making sure they’re above board and telling the truth about what they offer. is a good first site to start on when you start down the co-living trail. You’ll have to go to each site individually to really figure out of they have what you’re looking for and you’ll want to take your time and dig into it. It helps to stick to the bigger and more established communities like Roam, Common, Outsite and Unsettled but there are new ones popping up all the time and it pays to do your homework and look for updated lists.

Love or Something Like It

We’re all looking for love and connections with someone fun who makes us want to live each day to the fullest.

No matter what, finding people you really like is a numbers game. You’ve got to get out and meet people, try, fall on your face a few times and then get right back on that pony and ride again. If you’re great at meeting folks in real life, that’s perfect. But in today’s busy world with everyone trying to keep too many plates spinning at once, it helps to have an app.

That’s where Tinder, Bumble, Hinge and the myriad of copycats come into the picture. They all have their pluses and minuses.

Tinder is a granddaddy of them all. It’s filled with cat fishing, fake profiles, and booby traps galore. But it’s also the biggest and most popular and that means it’s got the most people on it. 

Since dating is a numbers game you want to be where the most people find themselves. And if you’re smart then it won’t take long to spot the fake profiles and the wastes of time. Give it a few weeks and you’ll start finding both lovers and friends through the app. I’ve done both.

If you haven’t used a dating app before, you’ve got to get over the initial stigma and feeling like you “need” an app to meet someone. Flush that garbage right out of your head. It has no place there. You don’t need to do anything. You want to date. That’s it. And this is just another way to do it.

Like everything else now, dating is digital. So don’t feel bad at all. Enjoy it. 

And don’t believe everyone who tells you these apps is just for hooking up. Sure, you can do that but you can do more than that too if you do it right.

You’ve got a better shot meeting someone online you really connect with than at the local bar or house party. It’s a bigger pool and you’re going to find people there you’d stand almost zero chance of running across in real life.

The biggest downside of Tinder is that it’s brute force, meaning you’re just looking at a picture and a few words of text so there’s not that much to go on other than “this person is hot.” There aren’t many filters or enhancements that encourage people to connect in a deeper way, so if you’re sapiosexual like me then you’re looking for a needle in a haystack. I need physical and mental attraction or it won’t work for me. 
Bumble is a twist on the Tinder formula. It’s big claim to fame is that even after you match, the woman has to make the first move and that’s brought high-powered and intelligent women to the platform in droves. I like it and I often find smart, interesting, well educated and lovely woman on there who seem fascinating. That said, I find the app hit or miss too.

The biggest flaw seems to be the time limit. Even after a match the woman only has one day to make the first move. That’s a good idea in theory but it sucks in practice. People are busy. Most people don’t have time to login to the app every day. They’ve got other things going on, especially if they’ve got their shit together. 

Because of this stupid “feature” it means perfectly good matches disappear unless the gal bothers to make the connection in that short time window. It’s a bad and poorly done example of gamification. Still it’s a pretty strong app otherwise and like Tinder it’s got lots of people on it so I still use and I’ve had some fun connections there.

The third one I’ve tried is Hinge. I like the concept a lot. Rather than just swiping left or right, there’s a little heart next to what people write about themselves and their various pictures. When you sign up you’re encouraged to do more than just post one or two photos like you do with Tinder. That’s good because it gives people something more natural to talk about on there. If someone says something witty and fun I can “like” that directly and send a little message with the like as well. That feels a bit more like meeting someone organically.

Hinge’s biggest flaw is it’s new and there aren’t as many people on it, depending on what city you’re in. If you’re traveling a lot you might find yourself “swiped out” because they’re just aren’t enough folks on there. That might change if the app grows but only time will tell. A dating app lives or dies with the amount and quality of people on it.

If you’re a part of the Illuminati or super beautiful you can try out Raya, the Tinder for Illuminati, but only if you have an iPhone (Android users are scum apparently) and only after passing a strict screening tests to prove you’re part of the beautiful people, the beautiful people. I’m not cool enough to be on this app so I can’t tell you if it’s any good but if you’ve got Gattaca level genetics than consider giving it a go and maybe you’ll hook up with a celebrity or someone else from the secret masters of the universe.

Frankly, none of these apps are perfect but you can meet folks on them if you’re patient and give it a little time and tweak it. There’s a lot of room for improvement and disruption in this space. I really wish someone would start one with some machine learning running it that matches people up better. Or maybe just one with a novel and unique interface or just better spam filtering. It seems like Tinder could spend a little more money to filter out all the fakes without a lot of difficulties but they aren’t doing it for reasons unknown.

That’s probably because most of the apps out there are owned by the same people, Match Group. They own Tinder and Hinge and a bunch of other platforms too. That makes most of the apps basically the same, each with their own strengths and weaknesses. 

Still, if you’re looking for love or something like it, and you can wade through the initial revulsion and the sub-par interfaces you might just find the person you’re looking for or at least the person you’re looking for right now.

Experiencing the Unknown

So you’ve got the AirBnB app but did you know it’s not just for finding a place to lay your head?
If you haven’t experienced AirBnB Experiences you’re really missing out. What are they? They’re everything from local food tours, to guided tours of museums by PhD students.

AirBnB Experiences are super easy ways to have fun in a new city or at home. Don’t be afraid to use Experiences in your home town! It’s a great way to get to know your own city in a brand new way.

Just pull up the AirBnB app or the website and type in a city and you’re off and running. Take your time going through them. Don’t try to find an experience when you’re ready to go out ten minutes from now. It won’t work. You have to take your time and go through them all. Read the write-up, look at the pictures, and read the reviews, including the negative ones.

Save all the ones that look good.

They have everything from a night of clubbing, to art tours, to learning how to make an incredible Thai meal.

The best part about AirBnB Experiences are that it’s pretty easy to meet other folks you want to hang out with later and often the host is a pretty unique person worth getting to know. I did one in San Francisco with painted staircases and the incredible guide knew everything about local plants and berries you could eat along the way which was amazing and unexpected. Don’t be afraid to exchange numbers and contact info with hosts or people on the tour if you hit if off. Don’t be pushy or aggressive, just ask nicely and let them know you really enjoyed your time and you’d be interested in hanging out again.

Pro tip: This is an amazing way to set up dates.

Most people take their dates to coffee or dinner or a bar. Boring!

I like to load up five or six experiences that are varied and fun, like hiking in canyons, a river cruise, dolphin watching and making pasta. Then if I’m hitting it off with someone, whether a friend or potential lover I casually show them a few potential days of fun and say “Should I go dolphin watching this week or learn to make fresh pasta?”

Watch their eyes light up and then invite them along to whatever one they like best.

Dancing the Night Away, Finding Places to Go and Things to Do

Culture Trip

Culture Trip is a fantastic website and one of the best ways to share in the collective wisdom of seasoned locals and travelers. They’ve also got a good app that mirrors all the content and filters it by the city you’re in now.

The site does a great job of getting writers who know the city they’re writing about, rather than people just faking it with regurgitated info from outdated guidebooks that suck anyway and don’t show you a damn thing that’s actually alive and thriving in a city.

Guest writers post about everything from their favorite hot spots, to contemporary art tours, to all night clubbing. It’s a lot like a more curated version of TripAdvisor. On TripAdvisor anyone and everyone can post and you never know if that person is just bitter because they showed up to a club in a Hawaii shirt and didn’t get in or if they just don’t like Dim Sum in the first place and shouldn’t be writing about how much Dim Sum sucks.

The writers on Culture Trip generally like their subjects and want to share their own unique experiences. You can’t trust every post because sometimes pro writers can crank out a passable listicle because they need to get paid but it’s pretty easy to tell the difference. If you’re looking for museums in New York City, look for articles that have some off the beaten path or obscure choices, not just the MOMA. You want some surprises scattered among the obvious choices because that’s a sign the writer did their homework or actually experienced what they’re writing about for real.

Real experience is everything because that’s what you’re looking for too.

The companion app has mixed reviews, but it’s worked pretty well for me. Even if the ticketing system on it gets busted during an update, the app is still a convenient way to find fun and inspiration in your city. I keep it on my phone and switch back to the website if the app is failing me for any reason.

Resident Advisor

If you’re looking to dance the night away then Resident Advisor is the app for you. Be sure to fill out your profile with your proper age because the app will hide some of the seedier aspects of life from you and that may be just what you’re looking for on this fine evening far away from home.

If dancing is not your thing, you won’t find much to love in this app, but who doesn’t love an occasional trip to the dance floor? RA does have categories for events and festivals but I find that almost every event is some kind of party and the local food festival or art gathering seems to be completely missing.


EventBrite is a big one and there is a lot of stuff on there. 

You can get tickets to events huge and small here, everything from the local swap meet to a blockchain conference or a gathering of cosplayers. It’s on my phone and I use it if I know exactly what I’m looking for but when it comes to finding new things I find it a bit of a mixed bag. 

On one hand it seems to have a million events and everyone posts their event there because the app has the eyeballs to make sure people see it. But that’s the problem. It’s not well curated and there are so many apps on there that it’s hard to find what you’re looking for without wading through a lot of swill to get it.

Use it to buy tickets for events in advance but know what you’re going to do before you get on there or you’ll just waste time.

Facebook Local

Facebook has an event section that’s buried in the local app and on the website. It’s hard to find sometimes. 

I’m amazed at the wide range of things that get listed there. Let’s face it, we all love and loathe Facebook at different times. It’s like the old man of the Internet. 2 billion people are on it, which is a quarter of the world’s population, which is totally freaking crazy to imagine even a decade ago. That’s a lot of connections and data points.

It’s tracking us, advertising to us, screwing with elections and everything else that bugs us about big tech and its abuses but it’s also just freaking useful at times.

Every major event in a big city tends to find its way to Facebook Local so it’s a must have for anyone looking to figure out what to do on any given Saturday or Sunday.


I know what you’re thinking. What the **** is Instagram doing here? 

I know. I know. 

Instagram is for self-absorbed fake Internet models and taking a bazillion selfies to bore the hell out of future generations when they look back at us in a thousand years.

But did you know you can search by a city and it will show you tons of the most recent photos from people there?

Yeah you will get a lot of selfies, but you’ll also see pictures of amazing races happening right now or incredible meals. It’s a great way to find restaurants or cool bars and watering holes or museums you didn’t know existed and that aren’t in the guide books.

Admittedly this approach is very non-linear and it will take a bit of scrolling but sometimes it’s just a fun way to stumble on something you’d never find otherwise. Along they way it’s a bit like sitting in a virtual cafe and virtual people watching too so it’s a fun way to pass the time while you’re looking for a good time.

All Trails and Gaia GPS

If you’re an outdoor person then All Trails and Gaia GPS are the apps for you. Both of them let you plan out hikes all over the world. They give you road, satellite and topographic maps. The apps keep track of where you’re going and all your activity. If you want to get out to the hills or the mountains these are the apps you need.

They have little features like sharing your locations with friends. Maybe the most interesting bits are the prerecorded trails that people leave behind for you. And it’s not just trails in the wilderness but walking tours in big cities that let you check out art or historical sites.

Staying in Shape

I use Freeletics when I’m on the road or at home to keep in great shape. If you want to feel good and live a long life you want to exercise regularly, plus it doesn’t hurt to be in shape if you’re dating and looking for love in all the right and wrong places.

A gym doesn’t work for me because I travel so much and I have no idea if I’ll have access to one. 

Don’t use that as an excuse to not work out! 

You don’t need weights or a gym. 

You can work out right in your house or your Airbnb. You can watch TV while you’re doing it or listen to Spotify and not worry about whether anyone is looking at you and judging you in some sweaty gym.

Freeletics has a little built-in AI that learns as you go. You can customize it to what you want to achieve, whether that’s muscle gain or endurance or both. It changes up the workout as you give it feedback. If you can’t do one of the exercises you can tell the app and it will change it up. 

You can also adjust little parts of the app, like telling it you don’t want to do runs and sprints if you’re staying somewhere super cold and don’t feel like going out in the snow. For every exercise it shows you, it even has a perfect tutorial for each one that shows you the right form, where to count each rep and what to pay attention to, like keeping your knees unlocked or your back straight.

The app is also really smart. It knows if you’ve been slacking off a bit. If you haven’t logged in for a few weeks it knows you’ve been naughty and it will offer to construct a custom “comeback” workout that goes a little easier on you. That’s a good thing because you don’t want to risk injury jumping right back in to where you left off. When you don’t workout for a bit, it’s best to go a bit softer and work your way back into it slowly but surely.

I use the paid version of Freeletics which gives you history tracking and advanced features. It’s really reasonable, so much so that I can’t even remember what I paid for six months. Just do it!

Going on Permanent Vacation

If you’re nomading around the world like me then you’re going to find all kinds of little tips and tricks out there on how to find awesome places to visit. But even if you’re not nomading, some of the sites that cater to nomads are great for anyone researching travel destinations that involve more than “I want to get hammered every day and lay on the beach for two weeks before returning to my stressful day job.”

I’ll save you another post on “how I became a nomad” or “finding work that let’s you work remotely.” Just Google those and you’re find 100,000 of them. It’s the most popular nomad article, followed closely by “I’m a year or two into nomading and here are all my tricks” (oh damn I just added another one here), and also followed by the inevitable five to seven year out post called “why I’ve stopped nomading and settled down with my soul mate.”

The truth is nomading is a pain in the ass as often as it’s amazing. I’ve loved seeing cities all over the world and learning to pack a capsule wardrobe and do a ranger roll and how to live with almost everything I own in a European size suitcase. But I haven’t had an apartment to call home in almost two years and sometimes you just miss your favorite spice and you can’t waste money on Paprika if you’re just going to use it for one dish.
One of the best sites for nomading is Nomad List and it’s also just a great list for anyone traveling. They break down each city with a chart that shows how good the WiFi is, what the weather is like, how hard it is to find a hospital, how easy it is to speak English there, and even more esoteric things like freedom of speech because you don’t want to get caned in some random place for spitting your gum on the sidewalk or shouting power to the people at a rap concert.
Here’s Porto as an example, where I spent a lovely short stint last year and where I’d love to return. The site is dead on when it says English speaking is okay but the weather is amazing and it’s super walkable, although those hilled cobblestone streets are a challenge after a night on the town sometimes.

Getting Around

I’m a bit directionally challenged. There I said it. I can get lost going four blocks to my favorite restaurant that I’ve gone to twenty times.

GPS to the rescue!

Google Maps changed the world and I use it all the time, especially when I’m bike riding in a new city. I’ll pop in my Apple Airpods and let the voice navigation mostly get me to the right place, with occasional random glitches and wrong turns down a side street because it just hit a cell phone dead zone. But its seriously awesome to have no idea where you’re going and have a little AI in your ear directing you as you ride an electric Jump Bike in a new and unfamiliar place.

The downside is that Google maps kind of sucks at time. It picks its own routes and those routes aren’t always the best choices. It also struggles with some cities that have different alphabets. Google Maps got me lost in Athens constantly, because the streets were named wrong and nobody knew what the hell I was talking about when I showed them a name that Google mangled and mistranslated.

City Mapper is your best friend when trying to navigate a strange city or even your own.

Get on public transportation with ease and get alerts when it’s time to get on or off the train or the bus. It shows you every step of the way and it works wonders. 

The best part about the app is it shows you multiple ways to get to a location. It’s doesn’t just automagically pick the best ways the computer thinks is right. You’ve got the power in your hands. Pick from one of dozens of routes sometimes, mixing in more or less walking and more or less stops.

The more you use the app, the more you find all kinds of little goodies inside of it. I noticed that it shows me which cars were the most crowded or empty at different times when I was getting on and off trains in Berlin. That’s a super awesome little feature.

It even shows you how much time an Uber would save you so you can figure out if it’s worth ponying up the extra cash to get their faster and avoid trying to get on the metro.

My best tip for you is to make sure to download a city you’re in before going out so it works offline. Nothing worse that having crap WiFi in a foreign city and losing your way for six blocks while you hold the phone up like a divining rod looking for a signal in the rain.

That’s All Folks

It’s a big world out there. There’s so much to do and learn and see.

When you first start trying to find a whole new way to live and learn and love, it’s a little overwhelming but once you start doing it you’ll gain confidence and courage. Pretty soon you’ll look like a natural and wow people at parties with your knowledge and fantastic stories. After you’ve hiked mountains in Greece and gone to a beach party in Portugal or found a co-living place in a strange new city you’ll feel like a brand new soul.

Whether you want to try white water rafting, or go on an exotic snorkeling adventure with my friend Nadia Aly or just get drunk at a local watering hole while butchering the local language with catch phrases you learned from DuoLingo there’s an app for that!

Whatever you want to do, you can do it.

The choice is yours. Life is an adventure.

But only if you get out there and dive into it.


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