CINDY SHEAHAN

CINDY SHEAHAN

Cindy is a "50+ vagabond, mostly-solo backpacker having adventures and getting lost and found across the planet." Her first foray into solo travel was at the ripe old age of 55. She has stayed in hostels to villas, housesitting, AirBnBs, lived in her campervan Tilly & Workaways on 3 continents. The entire time, remote managing 16 rental apartments in Denver.

Full-time World Traveler at Planet Earth
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About this Panelist

I’ve e stayed everywhere! From hostels to Tuscan villas, housesitting, stayed in a zillion AirBnBs, lived all summer in my campervan, Tilly, and done Workaways - meeting people and making friends all over the world. The entire time, I’ve remotely managed 16 rentals in Denver - some of them Airbnbs or rented to travel professionals.


In 2016 I took a leave of absence from my job as a software and sales trainer and joined two friends to backpack an incredibly gorgeous and rugged 130-mile hike in Ireland – The Kerry Way. After that, I stayed in Europe for 3 more months and visited the Amalfi Coast and Greece with friends, then traveled solo (for the first time!) to Portugal, Morocco, and Spain, staying in hostels, having adventures and meeting people from all over the world.


I was a changed person… I returned home after 4 months to my job in Denver but couldn’t get the travel bug to stop biting. So…I quit again for good in December 2017 and headed out to continue traveling – spending 4 months exploring Southeast Asia: Laos, Cambodia, Vietnam, Malaysia and Singapore, Nepal, and Bali.


In the summer of 2018, I tried housesitting in Tuscany at a 15th-century villa. Then, I explored the Croatian coastline, checked out ancient Montenegro, flew in a balloon in Cappadocia, paraglided in Madagascar, worked in an orphanage in Nepal, walked the Portuguese Camino, housesat in Australia … and haven’t stopped yet!!


In the summer of the pandemic, I bought a VW campervan and headed to the east coast of the USA. I (safely and carefully) visited friends and family, drove along the Blue Ridge Highway, kayaked with the ponies of Chincoteague, and hiked the gorgeous state of Maine.


In the fall I flew to Mexico. I enjoyed Oaxaca, Guanajuato, and Mexico City, renting a tiny studio apt in Coyoacan – Frida Kahlo’s neighborhood, and then headed south to Columbia. I spent 3 weeks in a Spanish immersion school and then adventured around Medellin, Bogotá, Jericó, and more!


Wow! The things I’ve seen, experiences I’ve had, the people I’ve met, and places I’ve been have been amazing, humbling, and magical. Being a digital nomad and working remotely is better than you’d guess!

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