Planning a round-the-world trip can be overwhelming, but it doesn’t have to be. Asking yourself the right questions about budget, timing, destinations, and travel companions will help you tackle the hard stuff with confidence. Here’s everything you’ll want to consider — whether you’re planning a six-month RTW adventure or a shorter multi-country journey — plus a helpful checklist at the end to keep your trip on track.

For context, I’ve taken many long trips, including a five-month round-the-world (RTW) adventure that involved living out of a carry-on while visiting ten countries across Africa, Europe, Asia, and the Middle East. How did I make that happen? Let’s break it down.

Plan Your Travel Companions, Budget, and Level of Spontaneity

A big trip involves three major questions at the start:

• Do you want to travel with company, or would you prefer to travel solo?
• What’s your budget?
• Do you want to plan ahead, or do you want to make spontaneous plans on the go?

Who’s Going?

First, you’ll need to decide whether you want to travel with friends or family, on a tour, or solo — or some combination of these.

Why do you need to answer this question before any other? Because it’s going to impact every other part of your trip, from cost to overall planning. To take a deeper look at the advantages and disadvantages of companionship vs. traveling solo, check out this blog post.

What’s Your Budget?

The budget question is important for everyone (okay, almost everyone — I’m guessing that Taylor Swift could pull this off without glancing at her bank account). You need to know how long your cash flow will last, whether you can stay in five-star hotels or hostels, whether you’ll be visiting Iceland (crazy expensive) or Cambodia (a budget traveler’s dream). I made a very, very rough spreadsheet at the beginning of all of this — here’s a snippet:

What did I learn from this? Unless you’re a budgeting wizard, you will spend more than you plan. My advice? Make a budget and then add a third on top of it.

How Spontaneous Do You Want to Be?

Then there’s the question of whether to plan the whole trip out in advance or whether to be spontaneous. If you want to be entirely spontaneous, you can ignore the rest of this blog post! If you want to plan, however, here’s what comes next.

Step 2: Plan for Your Travel Style and Seasons

Now you have to answer a few more significant questions — and I’d say you’ll need to answer them in roughly this order:

• What’s your travel style?
• When are you going to travel?

How Do You Like to Travel?

It’s important to know how you (and your companions, if you have any) like to travel. This will require a bit of reflection and self-awareness. Here are some questions to ask yourself:

• Do you like to relax in one place for weeks on end, go to the same coffee shop, and get to know the vendors at the local cheese shop? Or would you prefer to cover a lot of ground, seeing new things every day?
• In general, would you prefer to visit big cities, the beach, or the mountains — or all three?
• What’s your traveling energy level, on a scale of 1 to 10 (with 1 being, “I just want to lie by the pool,” and 10 being “I want to go surfing first thing in the morning, then try out paragliding in the afternoon, and then find the hottest nightclubs where I can dance until 2am”)?

When Will You Be Traveling

Next, you need to figure out when you’ll be traveling. If you’re headed to Asia, you need to know whether you’ll end up in certain countries during rainy (or monsoon!) season. If you’re visiting northern Africa, you need to know if it’s going to be so hot that you’ll melt in the desert. If you want to see Paris, you need to know whether shops will be open (hint: if you care, don’t go in August). You get the picture — seasons matter for everything from weather and packing to crowds and costs.

Do You Have Must-Visit Seasonal Destinations?

Also relevant to the “when” question is this: are there seasonal things you’ve always wanted to do that only a big trip will allow? I’ve always wanted to see the tulips blooming in the Netherlands –that’s something that happens in April, and it’s been impossible for me to do in the past because of my work schedule. So I very specifically planned to be in Holland in the spring as part of my RTW trip.

Step 3: Pick Your Locations

Now comes what may be the hardest question of all, because it’s the first one that requires serious decision-making: where do you want to go? If you have a lot of time, you have a lot of choices. Here’s how I worked through the “where.”

Do you have any bucket-list places you’ve always wanted to explore?

For me, besides the tulips, Jordan’s Petra was a must-see.

Are there places where you want to visit friends or family?

I am fortunate to have people I love spread out over the globe, so that was another factor that I took into consideration.

If you’re traveling with other people, are there places that they really want to go?

I wouldn’t have ended up there on my own, but Iceland was my husband’s idea …

… and my mom and I decided to take a tour in Turkey.

Are there places that you know you’ll feel comfortable when you need a break?

Five months of travel is a lot! Sometimes it’s nice to land in a place that might be less work, perhaps a spot where you know the language, the culture, or the food. For me, that place was Greece, one of my favorite countries in the world. It was just what I needed after less-familiar spots like Morocco and Senegal and before the craziness of Egypt.

What’s nearby?

Sometimes you just need to make decisions based on proximity and flight paths (pro tip: do whatever you can to plan your trip so that you can make it from place to place on nonstop flights). It’s worth sitting down with a map if you’re going to be covering multiple continents — but note that proximity on a map does not equal ease of travel. Morocco and Senegal may be just one country away from each other, for example, but you pretty much need to travel via the airport in Lisbon to get from one to the other.

Is there anything that you absolutely must have?

Do you need good wifi to work remotely (in which case, you can cross Egypt off of your list)? Do you know that you may need good medical care? Will a full month of gray skies kill your mood? Assess your needs before you pick your places.

Step 4: Make a Round-the-World Travel Calendar

Once you’ve answered all of those questions, how do you make a plan? Well, first I make a calendar.

Yes, that’s a paper calendar. It’s old fashioned, it requires a pencil, it’s a bit messy. But if I’m making a plan that stretches out over five months, I need to be able to see everything laid out in front of me. My thirteen-inch computer screen just won’t cut it. So I plan on paper, and I have one sheet for every month.

Step 5: Book Stays & Flights

Book accommodations and tours.

I know that it has its detractors for perfectly good reasons, but I’m a huge Airbnb fan because I generally like having a kitchen, a washing machine, and some space. So I spent hours (days, if you add it all up) looking at listings. You need to know your priorities when you do this — for me, it’s nothing less than a 4.8, preferably a place with a view or a bathtub (or both!).

Book flights and long train trips

I try to do this on the early side. Car rentals, buses, and short train rides can usually be booked closer to the last minute, though if you really want to get those done in advance, feel free.

Load all of your plans into TripIt

Wow, do I love the TripIt app. This app is a one-stop shop for keeping all of my travel itineraries, and using it is a snap (they’re not paying me a dime for this free advertising, but since I don’t pay for the app, I’m still coming out ahead). Here’s what part of a trip might look like — so helpful to have all of this in one digital place.

Step 6: Procure Visas and Travel Documents

Whether you’ll need visas depends entirely on (1) what passport you carry and (2) what countries you want to enter. Doing this research ahead of time is key, since some countries’ visa processes can be long and laborious.

Also, make sure your passport is up to date! You’ll need at least six months of validity before it expires in order to enter most countries.

Step 7: Pack Your Bags for Your Round-the-World Adventure

I’m putting packing at the end, but that doesn’t mean it should be the last thing on your list. If you’re traveling with no more than a shoulder bag and a carry-on for five months, you need to have planned this part really well. It’s not an exaggeration to say that I spent at least six months thinking about and arranging my stuff. Here’s my master packing list (not including the cold-weather clothes that my husband kindly brought to Iceland for me), and here are my very specific reflections on the clothes I took with me.

Step 8. Final Round-the-World Travel Checklist

Want all of this in one handy place? Here’s a planning checklist that you can copy and work through at your leisure.

Have fun with the planning!

Further Reading: Plan Well, Enjoy Great Places

Ready to follow your travel dreams? From packing light to planning where to go next, these posts will help guide your journey:

• 🧳 The Definitive RTW Travel Packing List — See exactly what I packed (and left at home) for a five-month round-the-world adventure
• 👕 5 Months in a Carry-On: Clothes for RTW Travel — Wondering what clothes to pack? Here’s an amazing guide
• 🏠 Airbnb Pros and Cons for Long Trips — Thinking about staying in Airbnbs? Here’s how to decide if they’re right for you.
• 🌍 How to Choose the Best Airbnb — A step-by-step guide for finding great Airbnbs, wherever you may be headed.
• ❄️ The Best of South Iceland — Iceland is a highlight for many RTW travelers. Here’s how to make the most of it.
• 🌆 Fun Things to Do in Kuala Lumpur — Southeast Asia is on many round-the-world itineraries. Here’s how to enjoy Malaysia’s vibrant capital.

If you love the logistics of travel, you might also enjoy my other posts on travel planning, packing lists, and destination itineraries — perfect for making your next big adventure unforgettable.