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This site documents our journey of combining our flexible work arrangements with our love of travel into a full-time, best-of-both-worlds adventure of a lifetime!  Our goal is to spend enough time in each destination so that we can ‘live like the locals’ – get immersed in the local culture, cuisine, and climate – and have experiences that can’t be captured in a typical weekend visit.  We rent fully-furnished condos and houses through sites such as Airbnb and VRBO along the way.  We focus on cities known for great food and experiences.  Great wine doesn’t hurt either!

While the main goal of our site is to share our ‘work-ation’ experiences with family and friends, we also would like to provide tips for other practical nomads, travelers, and vacation rental owners.  Who knows what new business opportunities may materialize based on this unique journey?


Pavilion Bar, Charleston

Our Itinerary

Our past, present, and future adventures include:

Charleston, SC (Nov & Dec)

St Helena, CA just north of Napa Valley (Jan-Apr)
Chicago (May-July)
Santa Fe (Aug-Sept) with 1 week in Albuquerque for the International Air Balloon Fiesta (Oct)
Palm Springs (Oct-Dec) with visits to Chicago and NYC

Scottsdale (Jan-Apr) with visits to Hawaii and Chicago
Vancouver (May-June)
Chicago (July-Aug)
Montreal (Sept)
Alexandria, VA (Oct-Dec) with a 2 week visit to Chicago in Dec

Just booked!  Santa Barbara (Jan-Mar) (plans to stay on the east coast shifted with the toxic algae and Dave’s work schedule!)

We would love any ideas that you have for us on destinations as well!

More Background

We experimented a bit with the idea of traveling to warmer weather locations while still working last year when we spent a good portion of Dec and Jan in Grand Cayman followed by a month-long trip of a lifetime to Africa in Feb (that was ALL vacation, no work!)  By staying state-side I plan to have better more reliable internet access, can more easily travel for work if needed (though rare for me), and Dave can more easily fly to his consolidated hospitals shifts.

I sold the condo in Chicago (at a great price!), put all of our stuff into storage, and hit the road on Nov 1 2015 – perfect timing to escape the winter weather!  Ultimately we would like to purchase an inexpensive fixer-upper in a warmer weather location (and put our home improvement skills to work and get more bang for the buck), buy or rent a smaller place in Chicago, and split our time between the destinations.  In the interim, we will enjoy the financial freedom of paying for only one destination at a time – and no home improvement projects that have consumed MUCH of our time and energy in Chicago for the last 7 years – Cheers to that!


-Cindy and Dave


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