Leah Wolf (left) and Ashley Lands (right), co-founders of Provincial Leisure. (Credit: Courtesy of Provincial Leisure)
How Two Childhood Friends Wound Up Living Their Italian Dreams
Ashley Lands and Leah Wolf are revitalizing a small Italian town through their travel business, Provincial Leisure.
In the summer of 2016, childhood best friends Ashley Lands and Leah Wolf were both at crossroads in their lives. Lands was learning to live with a chronic illness, dividing her time between her New York City job and frequent trips to Europe, where her condition seemed to always improve. Wolf, meanwhile, was living full-time in Italy with her children while going through a divorce. She found herself living in the small village of San Gregario da Sassola, located just outside of Rome. Around this time, the Italian government declared that thousands of towns across the country, Wolf’s included, were perilously depopulated – some were on the brink of total abandonment, while others were virtual ghost towns. Both craving a fresh start, Lands and Wolf began to seriously consider investing in the revitalization of one of San Gregario da Sassola. And that’s exactly what they ended up doing, by way of their travel and hospitality business, Provincial Leisure. The duo operates a number of nearby vacation rentals while pointing guests toward family-owned restaurants and cafes in town, and leading them on local day trips and tours. Diane Lane would be proud.
Here’s our lightly edited Q&A, from Ashley Lands The Story Exchange 1,000+ Stories Project.
How is your business different from others in your industry?
Our mission is to help small villages thrive while allowing locals to maintain their way of life. We achieve this through extensive research that allows us to target and attract the right visitors. Leah’s design expertise and my background in hospitality marketing combine to help us find the ideal customers — those who want to contribute, not just consume. We seek individuals who aspire to improve the community, not just enjoy a brief getaway.
Tell us about your biggest success so far.
My brother, Jason, recently pointed out something that made us all laugh – and made us all grateful. He visited Italy shortly after we opened our third rental property in 2023, and returned this summer. At dinner one night, he exclaimed, “I can’t believe it. There’s so much food now!” We were puzzled and asked, “Food?” He explained, “When I first came, the cafes didn’t even have sandwiches. Maybe a pizza for dinner. Now, every cafe and bar is serving meals all day. This wasn’t here the first time I visited.”
It might seem funny to measure success by food, but it’s very Italian. Historically, food signifies economic growth and prosperity. The businesses here are expanding, and people are thriving. This kind of progress helps places like San Gregorio da Sassola move into the next generation.
What is your top challenge and how have you addressed it?
Recently, we had to inform investors – who were eager to join us – that we weren’t quite ready for their involvement yet. This journey has been about learning to operate on Italian time. Coming from New York City, the cultural shock was eye-opening. I struggled to understand how things worked – it’s a different world here. Through nearly two years of experience, I now grasp why Italy holds so much untapped potential. You can’t succeed without the support of the locals and the community, and understanding them is crucial to accessing the right resources.
Have you experienced any significant personal situations that affected your business decisions?
Suffering from chronic illness. At first, you’re terrified you’ll never become successful again, and it’ll all come crumbling down because your health won’t hold. You wonder why you had to go through it in the first place. And I know for a lot of us, at times, you wish you didn’t have to keep going at all.
The flip side of that is, you learn how resilient people are. You realize that real struggle makes you seek deeper meaning in life. And you truly value life-long friendships, because many of the “fairweather” friends stop calling when you’ve declined too many dinner invitations. All of these things and more have made me the person that I am today.
What is your biggest tip for other startup entrepreneurs?
Starting is everything. I’ve seen so many incredibly talented individuals delay their dreams because they couldn’t take that first step. It’s natural to feel uncertain, to worry about failure. But remember, every journey begins with a single step — even if that step feels shaky or unsure.
Embrace the process, knowing that growth comes from pushing through challenges. Surround yourself with a team that supports you through thick and thin – people who believe in your vision, and who will cheer you on when doubt creeps in.
How do you find inspiration on your darkest days?
I have almost unwavering faith in my own abilities. Please don’t ask me if I can move a mountain – I will. The only other person I’ve encountered who is like this is Leah. We see a dilapidated house and envision it as a dream vacation home for someone. We see an abandoned cafe and know it could become the next big thing with a little love.
We both believe in ourselves. And it’s our favorite quality about one another.
What is your go-to song to get motivated on tough days?
I love music from the 1950s. Leah and I also make playlists together, which we jokingly refer to as “The Soundtrack of Our Lives.”
Who is your most important role model?
My role model is a combination of characteristics of everyone I love. No one on this planet is perfect. But each person, from the best to the worst, has something special to offer. This approach informs my lifelong philosophy about other people: Find that unique spark that defines them.
Instagram: @ProvincialLeisure
Check out our Advice + Tips for entrepreneurs starting-up
Watch our latest videos
Subscribe to our podcast