Travel Planning

My FAQ About Long-Term Travel

So, I’m leaving my “normal” lifestyle with a corporate job and a cool, downtown loft to travel the world indefinitely. Any questions? Well, when I share my plans with friends, family, and the people who serve wine samples at Whole Foods, I get a momentary blank stare, then, usually, a barrage of questions. These are some of the most common inquiries I receive.

However, no one has asked ANYTHING along the lines of “why would you do that?” or “won’t that be a terrible way to live?” Everybody has shown overwhelming support, genuine curiosity, and tangible excitement about it. So, if you’ve expressed these feelings to me, THANK YOU! It makes a nerve-wracking decision like this so much more approachable.

Many more views from the wing ahead!

For how long are you going to travel?

Currently, we have no end date. We’re going to keep at it as long as we’re still enjoying life on the road and have the funds to continue. We’re planning for at least two years, but hopefully longer! Check out my itinerary page, which will be constantly updated with details of our route.

Where are you going to stay?

We’re planning to stay in Airbnbs or similar apartment-style accommodations that give us privacy, space, and basic amenities. Being a couple, we appreciate having a private bedroom so we’re not planning to stay in hostels or a dorm-like setup. That being said, we’re looking for the cheapest possible places to stay that include a bed, private bathroom, basic kitchen amenities (fridge, microwave, and stove/dishes if we’re staying there for longer than a few days), and fast WiFi in a safe area.

What about health insurance?

I think this was one of the first questions my mom asked! Luckily for long-term travelers, there’s a whole travel health insurance industry dedicated to our specific need for care on the road. Travel health insurance covers you for any unexpected health issue, from emergency dental care (like if you break a tooth) to visits to the hospital for injury or illness. It will even cover you if something catastrophic happens and you need to return home via medical transport.

I did a lot of research on a provider that would work best for us, and I settled on World Nomads. This company gets a ton of press, and it seems like it actually deserves all the hype. The plan is affordable (we paid about $700 for our first 6 months of coverage – total), and you can file claims and extend coverage online. I’ve never been so excited about insurance.

And going to the dentist?

While World Nomads doesn’t cover regular dental checkups, I really like the clean feeling after visiting the dentist. So, I did some research on dentists around the world. And who knew, people everywhere go to the dentist too! Major cities, especially if they have a big expat population, even have US-trained, English-speaking dentists that anyone can go to for a checkup. The cost is a fraction of what a dentist in the US would charge, so I’ll be able to continue my biannual teeth cleaning routine around the world. My Miami dentist even emailed me my records so I can bring them to a new dentist in Singapore or Mexico City. Souvenir goals: tiny travel toothpastes from every continent.

How do you pack for a trip like that? / What are you going to bring?

My favorite question! Mostly because of the reactions I get when I share my answer. I’m bringing a regular backpack and a wheeled Samsonite carry-on. That’s it. No room for things I might wear or something to bring “just in case.” We’re keeping our stuff carry-on friendly to make it easier to transport on buses, trains, tuk-tuks, and ferries. And (most importantly) to avoid waiting around at the baggage claim!

I compiled a very detailed packing list that you can read here. TL; DR: one of pretty much everything, except enough socks and underwear to last one week. Work setup (keyboard, mouse, laptop stand). Five pairs of shoes. Minimal toiletries because you can buy what you need when you get there. And some fun stuff like a Polaroid camera, travel yoga mat, and Bluetooth speaker.

What will you miss most while on the road?

I’ll definitely miss my family and friends. But, the world is small and I’m confident that our paths will cross in the future. My family is already making plans to meet up with us in Asia and Europe! Also, a part of me will miss having a regular routine and the creature comforts of my own apartment. But, that’s a small price to pay for the infinite opportunities and endless adventure that I’ll find by being a modern nomad.

miami sunset
I’ll miss these gorgeous Miami sunsets from my balcony!

Are there any places you don’t want to visit?

Not many… The only places I would prefer not to visit are those that are truly unsafe for tourists. So many wonderful cities and countries get a bad reputation (like Mexico City!) but are absolutely wonderful to visit. So, I’m trying to keep an open mind and explore as much of the world as I can, without seriously putting myself in danger.

We’re also hoping to time our visits to countries with wacky weather so that we’re in town during the good weather. For example, not going to Malaysia during monsoon season.

Are there any places you’re especially excited to experience?

Does the whole world count?! A few places that I’m really looking forward to are:

  • Kyoto, Japan
  • Hoi An, Vietnam
  • Oman (looks breathtakingly beautiful and I’ve read so many wonderful things about this peaceful Middle Eastern country)
  • Germany in December for Christmas markets – hopefully December 2018!
  • Lake Bled, Slovenia
  • Cape Town, South Africa

And the elephant in the room… how are you going to afford it?

Two ways: remote work and savings. Ideally, we won’t have to dip into our savings at all. The amount of freelance work available online is astounding. It’s even super easy to find on sites like Upwork and People Per Hour. I’m fortunate to have a college degree and several great work experiences in the travel and hospitality industry, all of which gave me skills that are useful for online jobs. But any skills can be turned into a freelance gig with a little creativity and motivation.

While my blog is more of a passion project, and I’m not expecting to earn a livable income from it in 2018 at least, I am expecting to make enough from freelance jobs to break even on our travel expenses. Plus, the cost of living in most countries is significantly lower than in the US, so I won’t need to make as much money as I would need in the US (especially in Miami).

And, to supplement our earnings from freelance work, we’ve been steadily accumulating credit card points and frequent flyer miles from a slew of new cards we’ve opened in the last couple years. So we’ll cash in those points eventually to save some $$$ on airfare, especially on pricey long-haul flights to move us from continent to continent.

Well, that’s it for the most frequently-asked questions about long-term travel. Did I miss something that you’re curious about? Or would you like advice on planning your own epic trip? Ask away in the comments, or feel free to shoot me an email. Don’t forget to follow my Facebook and Instagram pages to follow along on my adventures.

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