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 for 15 years and seen all sides of it: this one is unmissable. And if you’re dreaming of the Italian Dolce Vita and want to take on a ready-made retreat site in Abruzzo, Kerry might just have something for you too. \--- Key Takeaways: - Always have a contract — even when the other party wants a handshake. Kerry’s insistence on a legal agreement from day one meant her exit from Camp Couture was clean, protected and on her terms. The contract should include ownership of structures, exit clauses and right of first refusal from the outset. - Think about your exit before you even open. It sounds counterintuitive, but building your exit strategy into the legal structure from the beginning — not as an afterthought years later — is what gives you real options when the time comes. - The asset and the business are two different things. Selling the business doesn’t have to mean giving up the asset. Kerry’s model of leasing the business while retaining the property is a genuinely useful framework for hosts thinking about stepping back without losing long-term value. - Running a business abroad requires deep cultural research, not just property research. Employment law, bureaucracy, banking, tax reporting and local staff expectations can be radically different — and those differences have real financial consequences that no amount of entrepreneurial mindset can compensate for. - Fully booked isn’t the same as profitable. Kerry’s audit revealed that 10 seven-night retreats would outperform 900 individual short-stay nights on profit — once real costs and owner hours are properly factored in. Know your numbers before you optimise for occupancy. - Building a business in a foreign country is possible — but go in with eyes wide open, not rose-tinted glasses. If you can’t conduct a legal or financial meeting in the local language, that gap will cost you, sometimes significantly. \--- Find out more about Kerry Roy and Cerchio Del Desiderio Retreat Kerry’s retreat in Abruzzo, Italy is available to lease — if you’re dreaming of taking on a ready-made Italian agritourism business, get in touch with her directly. Website: https://cerchiodeldesiderio.com/ Instagram: https://www.instagram.com/cerchiodeldesiderio\_retreat/ Facebook: https://www.facebook.com/profile.php?id=100063526805273# \--- **Do you have a marketing roadmap for your business?** No more winging it and feeling like you are in constant marketing chaos! Create your easy-to-follow marketing roadmap for the year ahead. My Direct Bookings Bootcamp is now available ON DEMAND! Let’s make this the best year yet for direct bookings! Head to my website for more info. \--- **What would you do with an extra £20k+ in your holiday business?** I've saved £100k in commission in 5 years by taking 100% direct bookings and now I show Airbnb hosts, holiday cottage and glampsite owners how to do the same. It is easier than you think to move to 70%+ direct bookings. If you currently rely on Airbnb or another online agent (OTA), take Sarah's FREE quiz here - it's time to give them the boot! \--- Connect with Sarah: Website Instagram Facebook LinkedIn \---