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BoldlyGo – Travel Well. Live Boldly

128 Countries Later: Caroline Lupini’s Points & Miles Fueled Digital Nomad Life (Ep. 122)

In this episode of Revolutionizing Your Journey, DeAndre sits down with Caroline Lupini to unpack what life really looks like as a full time traveler who has explored more than 128 countries.

They take you inside her transition from a traditional engineering career to building a location independent lifestyle powered by points and miles. Caroline breaks down how she chooses destinations, balances work while constantly moving, and structures her travel around opportunities that maximize value and experiences.

The conversation goes deeper into the realities behind the lifestyle, from handling taxes, health insurance, and logistics on the road to building routines that make long term travel sustainable. Caroline also shares how community, flexibility, and intentional planning play a key role in making this lifestyle work long term, along with the personal growth that comes from seeing the world through a completely different lens.

 

Key Highlights:

  • Caroline’s transition: She moved from engineering into full time travel by leaning into points and miles opportunities.
  • Destination strategy: Travel decisions are driven by points value, personal goals, and events like conferences.
  • Nomad reality: Remote work requires structure, planning, and constant adjustment while traveling.
  • Life logistics: Taxes, insurance, and mail handling are essential systems for long term travel.
  • Community matters: Connections and flexibility help sustain the lifestyle and unlock new opportunities.

 

Resources:

 

Interested in Financial Planning?

 

Need Global Travel Insurance? We recommend World Nomads

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

 

Connect with DeAndre & Taryn: 

 

Connect with Caroline Lupini: 

 

Publishing Tags: Revolutionizing Your Journey, DeAndre Coke, Caroline Lupini, Digital Nomad Lifestyle, Points and Miles, Travel Hacking, Remote Work Travel, Full Time Travel, Travel Strategy, Location Independent, Travel Rewards, Credit Card Points, Nomad Life Tips, Travel Podcast

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Bakir Djulic April 16, 2026
Written by Bakir Djulic

Bakir is a marketing manager with over a decade of experience in the variety of industries. Before receiving his Bachelor’s Degree in English Language and Literature, Bakir’s passion for information technology resulted in him starting his career as an IT clerk. After graduating from college, he embarked upon the journey in the digital marketing world, combining his passion for writing and his extensive knowledge in the IT industry. Bakir’s wide range of interests have resulted in him taking on various positions such as Social Media Specialist, Content Specialist, Account Manager and Copywriter. His mantra is ““Everything is learnable” and he works hard to stay up-to-date on the latest, constantly changing digital trends. When he isn’t working, you will find Mr. Djulich spending quality time with friends and family, reading a book, or exploring the latest from the tech and gaming industry.

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