Travel Mistakes We Made in 2025

Ask A Nomad – December 2025

Earlier this month, a group of 7 of us nomads, former nomads, and soon-to-be nomads met up on a call. Four continents were represented, with a special shout-out to Brad, who called in at 3:00 am Thai time, and Kat, author of Fifty & Free, new to our nomad commuity.

This call was the first time many of us globe-trotters met up IRL (sort of). We swapped travel stories, tips, and our biggest travel fails of the year (from full-time travelers who definitely should have known better.)

Don’t Make These Travel Mistakes in 2026

Sharing our hard-won lessons, so we can all be forewarned in 2026. Here are our epic travel fails of the year:

Linda Jackson, author of Shellphone Chronicles — calling in from Suva, Fiji

• 🚫 Don’t transpose the date sequence (month/day vs. day/month) on your visa, applying for your extension a month late.

• 🚫 Don’t depend on your mail to reach the United States when countries are refusing to mail to the States because of new tariffs.

Claire Polders, author of Wander, Wonder, Write — calling in from Buenos Aires, Argentina

• 🚫 Don’t underestimate the importance of Black Friday in South America, and be without a place to stay in the city.

Kasia Gurgul — calling in from Victoria, Canada

• 🚫 Don’t go to the wrong airport and miss your flight.

• 🚫 Don’t fly directly from sea level to the highest altitude capital in the world and suffer from altitude sickness.

Fun Facts:
Highest capital in the world: La Paz, Bolivia. Lowest capital in the world: Baku, Azerbaijan

Brad Yonaka, author of Odyssey & Meaning — calling in from Phuket, Thailand

• 🚫 Don’t ignore constantly changing visa regulations and requirements, thereby sending your wife to another country.

• 🚫 Don’t get caught without enough passport pages, especially during government shutdowns.

Teodora Gaydarova, author of The Local Insider — calling in from somewhere in Europe

• 🚫 Don’t go to cities, like Barcelona, where the rental situation is becoming absurd. Otherwise, you could end up sleeping on your friend’s floor (and kissing your friendship goodbye)!

Erin Michelson, author of Nomad Life — calling in from Barcelona, Spain

• 🚫 Don’t go to the airport at 3:00 p.m., when your flight is at 3:00 am. Start talking in military time.

• 🚫 Don’t mix up your passports. Pay attention to which passport goes with which visa application.

Kelly Benthall, co-author of Benthall Slow Travel, participated even though she couldn’t join the call. Hats off for the supreme effort.

• 🚫 Don’t plan your travels aspirationally; rather, plan for the travelers you actually are. If you continually think ‘we can totally do that,’ you may burn out.

🚫 #1 Epic Travel Fail of 2025

We won’t tell you, because Linda swore everyone on the call to secrecy, but trust me—it wins the prize for epic fail of the year.

Note: To get the inside travel scoop, be sure to join January’s call.

Join Us in January: Ask A Nomad on Jan. 7 @ 12:00 pm EST

Join the party and meet up with your favorite nomads and travel writers on the next Ask A Nomad call.

• Save the Date: January 7, 12:00 pm EST Substack *LIVE* event.

• January topic: Our nomad wish for 2026

• Meet Up RSVP: Get call details here

Join us, nomads, on January 7 @ 12:00 noon EST. If you’re interested in travel and remote work, you are invited. All are welcome! 🦋

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Christened “Wander Woman” by National Geographic, Erin Michelson has traveled to 130+ countries & all 7 continents. She is a professional speaker and author of the Nomad Life™ series of curated trips and travel guides, including the #1-ranked Explore the World with Nomads.

Curious to learn more about nomad life? Get the guide “Explore the World with Nomads: 50 Practical Tips, Interviews & Insights.”