Tulum. Costa Rica.

Tulum has gotta be up there. Best I’ve experienced at least.

Definitely. Probably the best nomad destination in LATAM.

exactly.

Only pay taxes back home, but if I were self-employed I could probably get away with paying next to nothing. Every place I visit is on a 3-6 month tourist VISA, so Airbnb is the only taxing me outside the States.

I overstayed in Mexico by 2 months and no one cared. I overstayed in Colombia by 2 weeks, and they’ll probably fine a couple of hundred bucks the next time I return.

BD for a startup & scouting for a VC firm, but I’m starting to get the itch to build… something small and manageable that can scale to a couple of million in annual rev.

Lucked out during COVID…

My US-based company went fully remote, and I started traveling LATAM. Never really looked back.

Nope. Whimsical & spontaneous perhaps but not spiritual…

I’m a pretty firm nonbeliever in anything that sounds like a fairytale. However, I do think traveling promotes the ability to let go and live in the present, which can be very healing and cathartic for many. You’ll also grow as a person and learn about yourself, so I can see why those who are believers of something greater would be tempted to package travel as the practice of something spiritual.

Hmm, I’ve been slomading through LATAM for the last 3 years now and the cut off to be considered a slomad is definitely 1 MONTH in a city/country and possibly staying up to a year… After that you’re either an expat or an illegal immigrant. 😂

I, and all the other slomads I know from USA/CAN, typically book month-long Airbnbs, almost exclusively, because we travel light and don’t want to be burdened furnishing apartments and then going through the hassle of selling items when we decide to leave. Some of my European friends claim to find better deals on Bookings.com, but the value difference seems negligible at a glance.

If you’re going to go the route of furnishing each place, its probably best to lock in 6-month rental agreements to make the energy and money worth your time.

I’ve done a lap and a half around LATAM over the past 3 years while working remotely. The first two years were solo, and the last year has been with two buddies I met along the way. I/we typically book month-long stays in Airbnbs and just hop to the next city or country over to keep flight times shorter and cheaper. All in, I’ve slow-traveled 12 countries in LATAM, some more than once.

As far as combatting boredom or loneliness goes, you’ll definitely need a routine and given your schedule is so flexible, here’s what to prioritize in structuring your days:

• Learn the language(s)
  • Speaking Spanish (or Portuguese in Brazil) will unlock such a richer and deeper experience for you as you’ll be able to connect with 100x more people and navigate day to day life with 10x more confidence.
  • If you’re starting from zero, you can probably get conversational in 8-12 weeks, depending on how much energy you put into it.
  • Take classes, ideally IRL, and you’re bound to meet some like-minded folks who are traveling a similar enough path as you are.
• Learn the dance(s)
  • Dance is a language on to itself. If you know how to Salsa, Bachata, or Samba, you can always make friends and will never be alone. It’s worth the investment to learn.
  • Best to find instructors who speak English. Classes are a good place to start but don’t hesitate to take a private lesson.
• Find a gym
  • There’s really no excuse not to get in the best shape of your life during your travels, and the best gyms for travelers are the ones that already have community baked in (i.e. Crossfit, MMA, Yoga, Pilates, etc).
  • You will always find a good mix of warm and friendly locals and foreigners in these spaces who can help you figure out your way around town.
• Learn a new skill
  • When I shared my initial itinerary with a friend, he mentioned that I would be passing through some of the best surf destinations in the world. I’d never been surfing before, so I decided to make it a new skill to learn. I surfed in Costa Rica and Ecuador but still need to do so in Brazil and Mexico.
  • Surfing also introduced me to spearfishing, which was one of the most meditative activities I’ve ever done! We cleaned and ate what we caught right on the boat, ceviche-style… “Mar to Mesa.” It doesn’t get fresher and more satisfying than that.
  • I also decided to try Muay Thai for my gym activity and lost 60lbs in my first 8 months. Now I’m training for my first amateur fight in my 30s and hope to visit Thailand soon!
• Do the touristy shit
  • Not only is it a good way to meet people and make friends, it’s generally just a fun way to pass the time. And no one gives better recommendations than a tour guide. It’s their job.
  • I went horseback riding for the first time in the Colombian jungles of Tayrona National Park, which has some absolutely stunning beaches. My tour of Machu Picchu was world class by any academic standard, and ATVing in Costa Rica brought out my inner child.
  • I really don’t know what all those judgey, anti-touristy people do all day when they’re nomading, if not the touristy shit, or why they think nomads have to choose.

As far as my overall experience goes, I really wouldn’t have changed much. Happy to share my recommended itinerary if you’re interested. Here are a couple of other things I learned though:

• Don’t plan too far in advance. If you find a place you like, stay longer. If you get the itch to explore again, then go. Always say yes to last minute trips with fast friends if you can.
• Figure out what environments make you happiest and try to recreate it wherever you go. A lot of people struggle to define what happiness is, but it’s really not that hard.
  • Make mental notes about all the situations where you feel filled with energy, excitement, peace or satisfaction. Then take mental notes about all the situations that drain you of energy, or fill you with frustration or anxiety.
    • Tulum, Mexico wound up being the place I was happiest. Life was simple, and I spent 8 months there training Muay Thai, meeting cool people from all over the world, experiencing gorgeous weather and beaches, scooting around eating delicious food.
    • The vibe was always chill and low maintenance. People were easy to meet and connect with. I cut my cognitive load in half and felt a lot more present in my life. I’m was born in big city kid, but it turns out I’ve really been a closeted beach bum all this time.
• Get comfortable being a little more forward than usual. You’d be surprised how far a simple opening line like “Hey, are you here for a weekend or here for a while?” will take you… a couple of life long friendships and dozens of spontaneous experiences in my case.
• The hardest part of being a nomad is when you find your tribe but it’s time for some people to move on. If you do half the things above right, this situation will inevitably happen… maybe even multiple times. Watching your travel friends pack up and go will bring a grown man to tears, but that’s evidence of time well spent. Remember that it’s never a goodbye with nomads, just a “see you later.”
• Traveling will spoil you and normal life will become almost unpalatable. Adventure is addicting. You’re likely to find that the idea of going back home to visit friends and family is entirely too taxing or burdensome. Some people feel guilty about that. Others just invite their friends and family to visit them abroad. Either way, it’s better to anticipate that you’ll be traveling for more than a year. When I got started, I thought I’d be away for 4-6 weeks. Three years later and my biggest fear is some BS return to office policy stripping away my new found freedoms.
  • I’m pretty confident you’ll see some of the business opportunities I have during your travels. Let me know what you come up with and maybe we can collaborate. My best investment so far has been Boundless Life, a turnkey solution for families who want to live a DN lifestyle. I’ve also been looking for…

1. A “Turbo Tax for DNs”
2. Easy virtual store/payments software for mom & pop shops and street vendors
3. A subscription model home-swapping site to compete against Airbnb
4. A “card/cash insurance” service for when you inevitably lose your wallet or can’t access an ATM for some reason
5. A dedicated portable digital whiteboard + collaboration software bundle for teams.
6. An engaging social network for DNs that makes access relevant information and connecting with people easier for nomads.

All-in, you’ll need at least $2500 if you’re traveling with friends. $3500 on your own. The dates add up.

I did this same trip but over the last 3 years. $2100’s not going to cut it.

I’d say you’d need $2500 to travel with friends. $3500 on your own. Minimum.

Go to an AA mtg. Seriously. I met a girl in Tulum who was in AA. Then I found out a half dozen of our mutual friends were in it too. I had had no idea. Very warm an welcoming place there at least.

Must haves…

• wifi
• power cord adapter
• credit card that allows you to take out cash.

Anything else is either nice to have or completely unnecessary.

Tulum, Medellin, Cartagena, Rio…

Feel zero guilt at all as long as my deliverables are high quality and on time.

I’ve heard multiple times that they’re not a good place to get work done. Too noisy, too distracting but otherwise fun.

Your taxable address will have to be somewhere in the US, ideally in a no income tax state like Florida. But I think you have figure out what states your company is registered to hire in. You can just ask your recruiter about what states employees currently live in.

After that, as long as the company is cool with 100% remote, I’d just get back on the road and head to Argentina.

It depends on where you go, how much space you want, and how much privacy you need. Cities like NYC, LA, SF & MIA will probably cost a minimum of $2000 for a studio, if you book several months in advance. But you might also want to try sites like Kindred, if you have a place to swap.

I’d probably prepare to set the following montly budget:

• accommodation: $2500 (1)
• groceries: $250/week (4)
• bus, metro, cabs: $250 per person (2)
• flights/rail: $250 per person (2)
• dinners: $100 per person (2)
• activities: $75 per person (2)

$6000/month is probably the minimal viable budget.

There isn’t a turnkey solution for slow travel and you will overpay for stays that aren’t at least 6 months in one place. Pick the place of interest closest to you, book a month-long stay, and just hop over the next closest city or country of interest every month or so.

It keeps transportation time and costs down. Do the whole trip in a loop, if you can. In 6-12 months, you’ll start gaining a sense for the kind of environments you like most… big cities, small beach towns, remote villages surrounded by nature, etc.

Spend more time in the environments you love most, and ground yourself in a routine…

• Learning language
• Learning dance
• Learning painting or photography
• Learning cooking
• Learning a new trade skill
• Practicing yoga, pilates, meditation, martial arts, etc.

Have a plan for meeting new people. Put yourself in a position to make new friends and connections. Everything else kind of takes care of itself.