Round the World Travel: The Complete Planning Guide

Week 6

This page is an archive of Week 6 content from BootsnAll's historical RTW contest and community challenges. While the original contest has ended, it remains a reference point for understanding RTW travel planning milestones.

What Holds You Back From Traveling?

What To Do With All Your Stuff While You're Gone

Leaving your belongings for RTW travel feels overwhelming but breaks down into simple decisions: sell the valuable stuff, store the sentimental items, donate/discard the rest, and handle the legal paperwork. Paying storage unit rent for a year costs thousands while your possessions depreciate. The better approach: before leaving, be ruthless about what actually matters and find homes for everything else. Most RTW travelers discover they didn't miss 95% of their stuff and end up selling more on return.

What Type of Person Goes on a RTW Trip?

RTW travelers aren't a monolith - they include 19-year-old gap year kids, 35-year-old burned-out workers, 65-year-old retirees, families with children, and digital nomads. People travel for radically different reasons: career breaks, relationship exploration, family bonding, spiritual seeking, or simple adventure. Dispelling myths about who "should" travel is essential - there's no wrong age, income, or motivation. Successful RTW travelers share flexibility and willingness to prioritize experiences over possessions rather than any demographic profile.

What is Your Why?

What is the reason you want to take a round the world trip? Is it something that you've really sat down and thought about? Have you come up with your "Why?" For most of us travel lovers, the initial answer is something along the lines of, "I want to see all the places I've dreamed about." But if y

What to Do With Your House When Traveling Long-Term

One of the biggest obstacles for people to overcome when taking off on a long-term, round the world trip is the housing situation, particularly for those who own. Some may feel completely tied down, but just because you own a home doesn't mean you are stuck. It doesn't mean you can't take a long-te

What to do With Your Job?

At this point in your trip planning, you probably have a plan together and have started researching heavily,  looking into costs of doing a trip like this, assessing your financial situation, and looking at possible routes. But what about job and career? For some, this part is easy. If you're one o

Where Do I Begin Planning a Long-Term Trip?

Where Does Wanderlust Come From

Where Should You Stay?

Accommodation choices define your daily experience and budget. Hostels offer sociability but often poor sleep. Hotels provide comfort but reduce interactions. Airbnb splits the difference. House-sitting is cheap if you plan ahead. Rooms in local houses offer authenticity. Luxury hotels exist if budget allows. Where you sleep matters: good sleep improves everything; bad sleep ruins days. Different accommodation types suit different travelers and trip phases - starting in hostels for community, switching to Airbnb for independence, occasional splurges on comfort. Budget travelers might need to prioritize cheap options; mid-budget travelers can be selective.

Why They Went (Adam and Megan)

People leave comfortable lives for RTW travel for wildly different reasons - escape, exploration, relationship deepening, spiritual seeking, career breaks, or simple adventure. There's no single motivating narrative. Some travelers spend years planning; others book flights on impulse. Some seek themselves; others already know themselves and want to challenge those assumptions. Understanding that RTW travel motivation varies widely helps you identify your own why without forcing a narrative that doesn't fit. Your reason for traveling is valid whether it's escape, adventure, learning, or just wanting a break from normal life.

Wine Tasting Around the World

If wine is one of your guilty pleasures, then why not plan a trip around visiting some of the world's great wine regions?