E016 - How to Travel Like a Boss!

This week on Across The Peak, Rich and I discuss how to travel like a boss! We talk about travel planning, safety and security considerations, and what you need to stay healthy.

Intro Stuff

Rich’s Drink: Backbone Bourbon

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Justin’s Drink: Wiseacre Brewing’s Gotta Get Up to Get Down Coffee Milk Stout

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The Show: Why You Should Travel

  • Challenge yourself! Challenge yourself to become more resourceful and resilient.

  • Change your perspective and challenge the assumptions you have.

  • Travel helps you appreciate your own life and the luxury it affords.

  • Traveling with someone else helps to build and strengthen personal bonds.

  • Travel promotes experiential joy:

    • Anticipatory joy - looking forward to the experience

    • Experiential joy - enjoying the experience in the moment

    • Post-Experiential joy - the memory of travel will last a lifetime

  • Have an adventure, do something crazy, get outside your comfort zone!

  • Escape and relax.

  • Celebrate! You are only guaranteed RIGHT NOW; tomorrow is a hope at best. Don’t put travel off for tomorrow.

Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.
— Mark Twain

Planning Considerations

  1. Where are you going?

    • Does it require vaccinations?

    • Will you need a visa?

  2. Why are you going there? Is this a business trip, personal trip, or other?

  3. What are you bringing?

    • Can you get by with less stuff?

    • Do you need to bring work stuff?

    • Are you traveling with a firearm?

  4. How are you getting there?

  5. Where are you going to stay?

  6. Who is paying for all this stuff?

    • What about rewards clubs? We think you should consider them but don’t get married to them for the points! Rewards clubs can suck you into brand loyalty that can make you blind to other experiential opportunities.

Take only memories, leave only footprints.
— Chief Seattle

Transportation: How are you Getting Around?

Trains and Rail Passes

Air Travel

Passports: if you don’t have one, GET ONE!

City Transit: What you need to know

  • Transit routes/maps

  • How/when you pay (cash, card, tokens, tickets, etc.)


  • Pay attention to insurance and licensing requirements

  • Know if you need a collision damage waiver (CDW)

  • Know if your credit card has supplemental collision coverage

Other Travel Considerations

Money, money, money!

  • Less is not more, more is more, but you can travel on the cheap.

  • We prefer to use local cash rather than credit cards.

    • Local cash is fun!

    • Avoid exchanging money at the airport exchange kiosks.

  • You may want to call your bank before you travel so you can access your money and lines of credit

Phones, electronics, and technology.

  • Universal Travel Adapters: This is an absolute necessity in most countries. We really like THIS ONE.

  • Phones: have the stuff to keep your phone charged

  • Wi-Fi and VPNs

    • Use caution with local Wi-Fi

    • Be reluctant to login to your accounts or pass your credit card number on public Wi-Fi

    • If you must use Wi-Fi, use a Virtual Private Network; we really like THIS ONE because it is secure, easy to use, and inexpensive.

Safety and Security

Sleeping, Eating, & STaying Healthy

Sleep - Refer back to Episode 7 for more information on how to get a good night’s sleep. To maximize your sleep consider traveling with:

Health/Hygiene - Be prepared for some traveler’s diarrhea.

Be a traveler, not a tourist.
— Anthony Bourdain

Justin’s Top Five Travel Tips

  1. Learn a little bit of the language: Hello, goodbye, thank you go a long way in the native tongue.

  2. SMILE! Get your head out of your smartphone and look friendly.

  3. Get comfortable getting out of the tourist traps - ask where the locals eat, drink, and hang out.

  4. Bring less stuff - optimize your packing, emphasize non single-use items, and go light!

  5. Justin's Planning Process: Plan loosely, have some things in mind but be prepared to change plans at a moments' notice. Don't get married to the itinerary.

Book of the Week

Europe Through the Back Door: The Travel Skills Handbook by Rick Steves

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Justin Carroll