Updated October 2022.
How would you like to spend two months at an Italian villa in Tuscany, living for free, in exchange for a couple of hours of work each day?
Um, yeah! Tell me how to make that happen, I thought. But before I dive into that, let me back up a bit…
Although I traveled extensively for work, I didn’t consider my six years of business trips ‘traveling solo’, as I was working and had a schedule to uphold. Yes, I was by myself and had to navigate cities, rent cars, figure out the subway system and eat dinner alone each night (which took some getting used to, but then was truly not a big deal whatsoever!) so I guess it’s technically traveling solo. During those trips, I began to extend my time in the cities where I was working to stay a little bit longer for fun – in Portland to visit the coast and the cool hipster neighborhoods, in Seattle to check out Vancouver and the San Juan Islands, in Florida to pop over to St. Croix in the Virgin Islands to visit my friend Rachel.
Extending these business trips made me see what a pleasure it was to travel alone. I was ready.
My first experience with long-term and solo travel was in September of 2016 – an incredible three month trip which began by hiking in the Amalfi Coast in Italy and seeing the amazing Pompeii ruins, then to Ireland (for an amazing 12 day, 130 mile backpacking hike with two friends on the Iveragh Peninsula through the many hued green hills and meadows of the Kerry Way)
…and next to explore glorious Greece – this six weeks of the trip traveling with various wonderful friends.
When all my travel buddies had expended all of their PTO vacation days and I was left on my own, I sat alone in my hotel room in Skiathos, Greece…took a deep breath, thought about it for a minute, and then booked a flight to Lisbon… and that began my solo travel! . I explored Portugal, Morocco and Spain, meeting amazing people along the way. I couldn’t have had a better time!
Once I was back at work in December of 2016 after this amazing and life changing trip, I couldn’t concentrate, couldn’t focus, couldn’t see myself plugging away at a job for another 10 years until the “usual” age of retirement. I wasn’t gettin’ any younger. I really felt that the time to travel was NOW – when I had good health and resources. I felt drawn to travel again…but how? How could I afford to quit my job, continue traveling and not go broke? I needed to come up with a plan as I had a very serious travel bug 🐞
A while back, my daughter Cara had turned me on to a website that changed my world: www.workaway.info. This site offers work exchange opportunities all over the globe. The listings let you know what kind of work you’re expected to do and for how long (Four hours a day? Five days a week?) and what you can expect to get in return as accommodations (a bunkbed with three other Workawayers? A cottage? A tent?) and any meals that might be included. And there are reviews from past Workawayers so you can read about their experience.
The options are so varied – you can work at a bed and breakfast in Prague. A ranch in New Zealand. A dive shop in Bali. A hostel in California. You can tutor adults in English in South Korea. Help small businesses with their social media in Barcelona. Nanny. Paint. Garden. Renovate houses. Pet-sit. Work at orphanages and schools. The list goes on and on. I love that you can research the options available before you decide to join, and becoming a member is only $38 for a year. I started digging in to the website to find somewhere that would interest me and provide a place to live and explore, while offering up a couple of hours of my time, energy and talent each day for room and board in order to make my money go further while traveling. That’s where I found this incredible opportunity as a caretaker at a villa!
In exchange for 2 hours a day of watering the grounds and tidying up the exterior I would be provided with a caretaker’s apartment at the top of a spiral staircase in a 15th century Italian villa in the Tuscan countryside. They were looking for a commitment of two months.
Yes.
Please?
So I contacted the owner of the villa (an Italian count, fer gawd’s sake!!) and he asked for two letters of recommendation and a little bit about me and why I was interested and a few weeks later, The Count (Agostino) asked me if I’d like to take August and September of 2018. Again…yes, please.
Sounds perfect…which led to me quitting my job (one more time!) in December of 2017 but this time for real. They weren’t surprised – I think they were wondering when ‘the other shoe was gonna drop’ after my first big trip ended, but my team couldn’t be any more excited for me and they were so supportive! 💜
This is all about saying yes. Granted, you need to have some financial resources in place, but believe me when I tell you that you can have a great time in Southeast Asia for about $1000/month. Paris? So expensive, everyone says. But I spent $40/night to stay in a little hostel and took the subway everywhere, spending only a coupla hundred dollars for the entire 4 days I was there. But what about airfare? It was less than $600 for a round-trip ticket to Paris from Denver. And there are loads of discount airlines in Europe (and Asia) that will get you from Point A to Point B for merely a song.
And what about my condo? I decided to rent it, completely furnished (dishes, pots and pans, linens, bed, Netflix, WiFi, all utilities included, etc) to travel nurses while I’m away. These gypsy souls take 12-week contracts around the country in order to work and be able to see the USA while doing so.
I live within walking distance of four or five major hospitals so it’s perfect! They are happy to find a nice clean place to live where everything is set up – all they need to do is bring their clothes and unpack! My personal stuff is in bins in the basement, and I’m making a couple hundred dollars above and beyond my rent which helps fuel my travel. Voila!
And now here I am in Tuscany (TUSCANY!!! Holy macaroni!!) living for freeeeee in a villa by just spending a couple of hours each day with a hose and a broom, picking up cigarette butts around the villa and watering a bunch of plants. 
Honestly. If you want something badly enough, you can make it happen!My next blog post will be all about the Villa – Villa di Corliano, in the San Giuliano commune (area) of Tuscany, just a short bus ride from Pisa or Lucca. This 15th century estate is ahhh-mazing! I’ll have photos galore, so watch for the next installment.
Grazie!
and Ciao!
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See you there! 😉
Travel is all about the gorgeous feeling of teetering in the unknown. Anthony Bourdain
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