How to Plan a Trip Around the World

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Planning for long-term travel is hard. Even for a list-loving Virgo like me.

When we agreed to embark on an 18-month journey around the world, I became totally obsessed with finding any and all information that could help us plan the BEST. TRIP. EVER.

At some point, I lost count of how many articles I read and websites I bookmarked while on a quest that, I’m pretty certain, took me to the end of the internet and back.

So what did I learn?

The struggle is real, people. Maintaining your energy and excitement for this crazy adventure, while also tackling a growing to-do list and managing all of the responsibilities of your “normal” life, is a legitimate challenge. It’s an emotional roller coaster of highs and lows, and with so many critical decisions to make and tasks to accomplish, it’s easy to experience a wicked case of travel fatigue before you ever hit the road.

Fortunately, we quickly discovered that the key to our success – and sanity – was surprisingly simple: stay focused on the big picture, stop obsessing over the minutiae and take this process one step at a time.

Step 1: Make the Commitment

The first step is the hardest, but it all starts here. For years, we’d longed to see the world. But until we made a conscious choice to act on that dream, we weren’t prepared to turn it into a reality. Whatever your motivation to travel may be, just make the commitment and don’t look back.

Step 2: Know Your Travel Style

Be honest about the way you like to travel, from accommodations and transportation, to your choice of destinations. This is the ultimate opportunity to push the limits of your comfort zone and experience new things, but be true to yourself and your interests. Knowing what makes you happy, and what doesn’t, will help you develop a more fulfilling itinerary and a more realistic budget.

Step 3: Build Your Dream Itinerary

Whether you call it a “bucket list” or not, most of us do have a running roster of dream destinations that fuel our fire for travel. Start there. These must-see places, activities and events can form the pillars of your chosen route, but don’t forget to make room for the unexpected. Some of our most anticipated and beloved stops are those we’d never even heard of before we started on this journey.

Step 4: Determine the Cost

Now that you know where you want to go, and how you want to travel, you can begin to determine how much it will actually cost you to take the trip of your dreams. The good news? The dollar is stronger than it has been in years. The bad news? Unless you’re fortunate enough to have an unlimited bankroll, this is where the tough decisions will need to be made.

Step 5: Develop Your Budget

There are two primary ways to fund your travels. (Neither of which includes a winning lottery ticket.) You can save money. Or you can make money. For most of us, the ratio will include a whole lot of the former and a little bit of the latter. Now is the time to realistically assess your monthly budget and determine your best strategy to cut back on expenses, live below your means and save every extra dime until you’ve met your financial goal.

Step 6: Set Your Departure Date

Make it official. Pick a departure date that provides you with a reasonable amount of time to reach your target budget. Other factors to consider? Try to accommodate any personal or professional obligations that are already on the calendar, and if you’re chasing summer, as many long-term travelers do, be sure your departure date aligns with the appropriate season for the first stop on your itinerary.

Step 7: Get Organized

Once the date is set, work backwards to create a comprehensive checklist tracking all of your critical travel and planning deadlines. Trust us. During the inevitable craziness of your final weeks at home, you’ll be happy you did.

Step 8: Work It Out

Will you work from the road? Quit your job? Or request a sabbatical from your current position? Your employment status could have a major impact on your trip planning, including where you travel, how fast you move around, and whether you’ll have a sustainable source of income while you’re gone. Don’t leave this up in the air. Make the decision early, so you can move forward accordingly.

Step 9: Provide for Your Pets

If you’re anything like us, the ability to provide for the care and well being of your pets in your absence is one of the few deal-breakers that could derail your adventure. So make it a priority to identify a caretaker. And then thank them every single day for their willingness to offer a safe, loving and temporary home to your four-legged family members.

Step 10: Book Your First Stop

Once the major decisions have been made, it’s the perfect time to take the leap and book the first stop on your trip. Want to walk on the wild side? Make it a non-refundable purchase. Risky? Maybe. But sometimes we need a big, grand gesture to shout, “I’m doing this… and there’s no turning back now!”

Step 11: Share the News

At this point, you’ve probably informed family and a few close friends about your plans to travel long-term, and you may be ready to start sharing the news outside of your inner circle. Brace yourself for the resulting response (including, but not limited to: shock, confusion, excitement, happiness, fascination, jealousy and denial), and try to have an “elevator speech” ready to go, to help you quickly summarize what you’re doing and why.

Step 12: Manage Your Possessions

What will you do with your house? Your vehicle? All of the personal items you’ve collected throughout the years? Ultimately, much depends on how long you’ll be gone and what your plans are for return, but this is a great opportunity to deliberately minimize the “stuff” that may be weighing you down both physically and financially. So sell what will help you fund your travels, donate what might bring value to someone else, trash the junk and save the items that matter most, making the appropriate plans for extended storage.

Step 13: Care for Your Health

No one wants to cut their trip short due to illness, so take steps now to address any potential – and preventable – issues. Visit your local travel health clinic to determine the recommended vaccinations for the places you plan to visit. Schedule appointments with a full battery of medical professionals, including your primary physician and dentist, as well as any relevant specialists (ideally, while you’re still covered by an employer-subsidized health plan). Then sign up for travel insurance and stock your medical kit, to ensure you’re protected on the road.

Step 14: Prepare the Paperwork

Make sure your passport is up to date, with plenty of extra pages for all of those new stamps. Research the entry requirements for the destinations on your itinerary and have a few extra photos made for online and on-site visa applications. On the home front, save digital copies of important paperwork (like your marriage and birth certificates, insurance policies, etc.) and assign a trusted friend or family member your power of attorney, authorizing them to act on your behalf in the event of an emergency.

Step 15: Organize Your Finances

When traveling internationally, and on a limited budget, don’t leave money on the table by paying unnecessary foreign transaction fees or missing out on the benefits of a great rewards program. Research your best options for credit cards and checking accounts, applying early enough to take advantage of the best available sign-up bonuses. Also a good idea? Meet with your accountant to determine whether any of your travel plans will qualify as a business expense, and if so, how to structure and manage your accounts.

Step 16: Decide What to Pack

Are you willing to check your bag, or would you rather stick with a carry-on? Are you packing for multiple climates? Or participating in any activities that require special clothing or gear? Don’t forget to consider your technology needs as well. Are you bringing a mobile office or planning to completely disconnect? If your travel dreams don’t include washing your clothes in the sink every other day, that’s perfectly fine. But when you’re limiting your possessions to what you can comfortably cart around the world, remember that every single item counts. So think carefully about what’s important enough to make the cut.

Step 17: Establish Your Communication Channels

Putting a solid plan in place to stay in touch from the road is a big deal, whether you’re connecting with clients or just regularly reassuring your parents that yes, you are still alive. If you’re traveling with a smartphone (and for so many reasons, you should), you’ll need to determine whether to sign up for a global plan, purchase an international SIM, or buy a local SIM for each destination. For face-to-face conversations, consider setting up FaceTime or a Skype account. (And build in time to hold a tutorial session for the previously referenced parents.) Then update your social media profiles and send the links to your personal and professional contacts, along with your preferred email address and phone number.

Step 18: Say Goodbye

In the end, the only thing left to do is say goodbye. Get around to updating that address book, so you can send everyone postcards from far and distant lands. Eat your favorite foods, so your last tastes of home are the best ones. Visit your favorite places. Love on your pup. Spend quality time with your family and friends. And throw yourself one hell of a goodbye party.

Because life as you know it is about to change forever.


There are 4 comments

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  1. Wendy

    Beautifully written – every topic. Had to stop from immersion for a moment to let you know! Loving everything about what you are doing ! Savor it! Now, on to the next segment……

  2. Lindsay Powell

    my sorority sister Rhys has just departed to travel the world solo for the next two years starting in Uraguay literally tomorrow So brave you guys are…she’s also climbed Everest and Kilmsmjaro…I doubt there is much she won’t do. I need to connect you two. She started a blog for this journey too. I envy your journey and had no idea you guys were going to be on the road that long…so glad you’re doing this for YOU before you start your family. Now our two weeks in Australia looks so weak! Love following you! Stay safe and write a book!

    • Jennifer Mikosky

      There is nothing weak about making it all the way to Australia! I love hearing about others out on the road… and super impressed by her accomplishments. Definitely put us in touch!

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