How do you Sell a Successful Short-Term Rental and Retreat Business? with Kerry Roy, Cerchio Del Desiderio Retreat

What actually happens when you want to move on from a business you’ve spent years building? And what does it really look like to take that dream of running a retreat abroad and live it out — with all the complicated, unglamorous bits included?

Kerry Roy is someone Sarah describes as glamping royalty and it’s not hard to see why. She was one of the earliest glamping pioneers in the UK, building Camp Couture from scratch on a 250-acre Yorkshire estate in 2012, growing it to 19 units plus pop-up bell tents, launching one of the UK’s most celebrated wedding festival venues, and running an annual campervan festival for thousands of people. All while planning her next chapter: an award-winning agritourism retreat in the mountains of Abruzzo, Italy.

In this episode, Kerry walks through the full arc of that journey: from the legal contract she insisted on from day one when the landowner wanted a handshake deal (a decision that protected her completely when it came time to exit), to the Covid timing that made selling Camp Couture both easier and more necessary than she’d anticipated. She’s honest about the financial realities of building on rented land: the high rent that meant weddings, not glamping, were what actually sustained the business, and the important distinction between selling a business and giving up an asset.

Then there’s Italy. Kerry is brilliantly candid about what running a hospitality business in a foreign country actually involves and it’s not the Dolce Vita fantasy.

From employment law that heavily favours employees (making hiring feel like a trap for employers), to bureaucracy that can’t be automated, quarterly financial reporting, bills still paid by queuing at the post office, and the sobering experience of having to walk away from a £40,000 legal dispute simply because she couldn’t fight a court case in Italian. She’d go back and do enormous amounts of it differently.

What’s particularly interesting is where Kerry has landed now: auditing her business forensically and discovering that 10 seven-night retreats would generate more profit than 900 individual short-stay nights, once costs and hours are properly accounted for. It’s a quiet but striking argument for rethinking the model entirely and a reminder that being ‘fully booked’ isn’t the same as being profitable.

If you’ve ever dreamed of running a business abroad, are thinking about your own exit strategy, or just want a genuinely unfiltered account from someone who’s been in this industry