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Travel for a Year

The idea of spending a year on the road appeals to a lot of people, and we were no exception. It’s not impossible. With the right planning and commitment, you can make it happen. So, we’ll use this article to talk about our experiences and step-by-step recommendations for how to travel for a year. 


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In addition to writing about his and Jenna’s travel and work adventures, Chipp is a CPA and founder of Walutes Capital, a real estate development and accounting firm. Wearing this “other hat,” Chipp offers real estate investment and development consulting services to clients. If you’d like help with your own real estate investing journey, contact Chipp here to set up an appointment! 

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How We Traveled for a Year


Full disclaimer: our year on the road wasn’t the result of some last-minute, Eat Pray Love-style drop-everything-and-go epiphany. Yes, we had the idea to travel over a few glasses of wine (who doesn’t!?), but we were only able to successfully do it by building a concrete plan - and sticking to it. 


A couple years before Chipp wrapped up his time in the Marines, we were sitting on the couch, wine in hand, talking about how neither of us wanted to fall into an Office Space grind. We didn’t want to wake up 20 years later realizing we never actually went out and saw the world together. The answer? Let’s take a year and travel! 


Grabbing a notebook, Chipp sketched out a rough timeline with the milestones we thought we needed to hit before taking off for a year. Broadly speaking, Chipp had to gain some professional experience and marketable skills to make some money while traveling. Jenna would eventually transition from full-time employee to part-time contractor with her current company, also to help keep cash coming in. We had rental properties that we didn’t want to deal with changing tenants while overseas, so we had to ensure leases extended through our planned travel dates. And, we had to figure out where we would live upon returning from our travels. 


Looking at these milestones and plenty of smaller wickets we’d need to hit, we came up with a roughly three-year runway. At the end of that period, we’d take off. And, we did. From the major milestones to the pre-travel administrative loose ends we had to wrap up, we stuck to our plan. Eventually, we booked the first leg of our travels - flights and a long-term AirBnB in Istanbul

The takeaway? With enough time and planning, you can travel for a year. But, very few of us have the money or flexibility to just drop everything and go. In the rest of the article, we’ve translated our own planning and travel experiences into a step-by-step guide. Hope it helps!

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Step 1: Make a Pre-Travel Financial Plan

For better or worse, cash is king. If you can’t pay for your travels, you can’t travel. As a result, the first step in traveling for a year entails laying out a plan for how you’ll finance your travels. Generally speaking, people have three options:


Option 1: Use Your Savings to Travel


This route made us extremely nervous. Frankly, we felt we were too young to drain our savings to fund our travels. And, we knew that, when we got home, we wanted to start a family - didn’t want to cross that bridge while broke. 


But, in the right situation, this can be a solid choice. For example, say you’re young, single, and know you need to go back to school to advance your career. Maybe it makes sense to work really hard for a couple years, stash away some money, and hit the road. Who cares if you’re broke when you get back? You’ll be going to school and diving back into a lucrative career anyway. 


Option 2: Work Remotely and Use the Cash You Make on the Road to Travel


Alternatively, you can find a way to tread financial water. Instead of living off your savings, you find a way to work remotely, so the cash you make offsets your travel expenses without the need to use your savings. This also exists on a spectrum. You don’t necessarily have to work full-time - just enough to cover your costs. 


Option 3: Combination of Options 1 and 2


Options 1 and 2 aren’t mutually exclusive. And, we ended up using a combination of sorts. For daily expenses, our remote work brought enough cash in to live comfortably. But, there were also a couple experiences we really wanted to do that would require tapping our savings. For example, we had an opportunity to go on a safari in Tanzania - couldn’t say no to that! But, our monthly income definitely wasn’t going to cover the price tag. Instead, we made the decision to pull cash from savings to do it, and we certainly don’t regret that decision!  


The Importance of Lifestyle and Financial Budgeting 


Regardless of what path you choose to finance your travels, make a budget! First, that means defining what we call your “lifestyle budget.” That is, how are you going to live on the road? Are you going to crash in hostels and eat street food in Southeast Asia, or are you going to stay at the Four Seasons and eat at Michelin star restaurants in Western Europe? 


How you plan on traveling dovetails directly into your financial budget. We’re not believers in building a spreadsheet to track every penny you spend - too stressful and time-consuming. But, we did insist on setting a broad monthly budget, to include average nightly housing costs, meals, entertainment, and travel between places. Once you establish this budget (largely driven by how much money you’ll be using from savings or making working remotely), you can actually plan your travels. When we were staying in more inexpensive apartments, we knew we had more cash for food and entertainment. If our housing and transportation costs were high in a given month, we’d do more cooking at home.

In Cape Town while traveling for a year

In Cape Town while traveling for a year

Step 2: Wrap-up Pre-Travel Admin Loose Ends  


Once you figure out how you’ll finance your travels, you need to wrap up those pesky administrative loose ends. These are the things that, while seemingly small, can potentially derail your travels or cause you huge headaches while overseas. Though certainly not an exhaustive list, here are some of the key admin tasks you’ll need to complete before departure:


  • Renew or order a passport

  • Break your lease (if renting)

  • Rent or sell your home (if owning) 

  • Buy a travel medical insurance policy (don’t want to be on the hook for thousands of dollars if you get malaria somewhere!) 

  • Confirm a plan for where you’ll live when you return (no fun wrapping up a trip and not having anywhere to go…) 

  • Move your household items into storage

  • Set up a mail scanning or forwarding service 

  • Sell or store your car and update your auto insurance

  • Make sure you’re up-to-date on all shots for places you plan on traveling (e.g. get your “yellow card” for yellow fever)

  • If you require regular medication, secure a year’s prescription (or confirm ways to get more while traveling) 

  • Identify a close friend or family member to troubleshoot Stateside issues that may arise while traveling (never know what emergencies can pop up!)

  • Related to the above, consider granting a trusted individual power of attorney

  • Write a will (macabre, yes, but critical if you have any assets) 


Hopefully the above list provides some guidance and a foundation for your own unique admin requirements. Whatever you end up identifying as your critical admin tasks, we highly recommend building a checklist with no-later-than dates for completion. This will keep you organized and serve as a sanity check to make sure you don’t forget anything. 


Step 3: Broadly Outline Your Whole Year


A year is a long time to travel, and a lot can change. It’s silly to make a dinner reservation before you leave for your 300th night abroad. Instead, make a broad outline of your entire year on the road. This will serve as a framework for your travels without wasting your time making detailed plans that will inevitably shift. 


Some of the key “big picture” plans include:


Departure and Return Date 


These bookends will factor into your above financial plans and admin tasks. And, when you’ve defined the front and back end of your trip, you can begin to focus on the details of each individual leg. 


General Geographic Areas and Directions of Travel


Yes, your daily and weekly travel itineraries will inevitably shift. But, it helps to create a general outline. For example, you may want to start in South America before flying to New Zealand. This will drive considerations on available flights and associated costs. Alternatively, you may only want to explore Southeast Asia. This potentially means you only need to consider major flights to/from there and can minimize transportation costs while actually living overseas. 


Regardless of what you decide, a broad outline provides shape to your travels and drives the detailed planning you’ll conduct for each individual leg of the trip. 


Step 4: Book and Plan the First Leg of Your Travels  


With a broad outline set, you can get down to planning the nuts and bolts of the first leg of your travels. This is the detailed planning discussed above. At a minimum, for your first destination, you should:


  • If required, secure a visa for your first country (this may require a trip to an embassy in the States, buying one online, or simply paying for an entrance visa when you arrive)

  • If required, learn some key phrases in your first country’s native language (‘hello,’ ‘goodbye,’ ‘thank you’, ‘excuse me’, and ‘sorry, I don’t speak [insert language]’ all go a long way in establishing credibility with locals) 

  • Book your flight

  • Book your first lodging

  • Confirm how you’ll get from the airport to your first lodging


Unfortunately, many people overlook this final task. Traveling to a new country, especially one with a different language, can be pretty overwhelming. Arriving outside an unfamiliar airport, you absolutely don’t want to have a panic attack while cab drivers and vendors are yelling at you in a foreign language. 


Instead, from the comfort of your own home, confirm exactly how you’ll get from that first airport to where you’re staying. This may involve confirming Uber works in that country and where rideshares pick up in your destination airport, reserving a shuttle, or mapping out the public transportation you’ll take. Whatever route you choose, make sure to plan it in advance. 


Step 5: Book and Plan Subsequent Travels 


Once you’ve settled into life in your first location, you basically begin a planning rinse-and-repeat cycle. Within the context of your broad, year-long travel outline, each individual leg feeds into the next one. 


For example, after our time in Istanbul, we headed to Ukraine to visit Jenna’s family. From there, we decided to return to Turkey to see a different part of the country. While in Ukraine, we confirmed our next destination city (Izmir), found an AirBnB apartment in the city, booked a flight, and confirmed that we’d be able to get an Uber from the Izmir airport to our apartment. If we had instead tried building a detailed itinerary for our entire trip, we wouldn’t have had the opportunity to hear about how awesome Izmir is from people we met in Istanbul and update our travels accordingly! 


For the rest of our time, we repeated the same cycle. We’d get to a new place, explore, meet people, and get recommendations for cool places to see next. Then, we’d take those recommendations and build a detailed itinerary for that next step - all within the broader bookend of our defined return date. That’s also how we ended up spending a month and a half camping and traveling through Namibia, a leg of our journey 100% inspired by people we met in South Africa who raved about the country. 


Step 6: Be Flexible!

Last but not least, be flexible! Even the best laid plans can fall apart, and surprises (some good, some less so) inevitably pop up on the road. When you travel for a year, you have to embrace some element of the unknown. Bumps in the road are just unavoidable. But, if you take a flexible approach to things, you can translate any situation into a happy little accident!

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Affiliate Disclosure


We’ve included affiliate links on this page. If you click on a link and end up buying something, we may receive a commission (without adding any costs to you). This helps us pay the bills, and we only promote products and services that we personally use and wholeheartedly endorse. Thanks so much for the support!


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