april, 9th 2026
What really happens behind the doors of a Tuscan villa?
Reading time : 5 min
If you’ve been following me for a while, you probably know that part of my work often takes me inside some of the most beautiful villas scattered across Tuscany. Sometimes they are just a few minutes from home, sometimes hidden deep in the countryside, surrounded by silence, olive trees, and that kind of light that only Tuscany seems to have.
And almost every time, I receive the same questions. How does it actually work to rent one of these villas? Where do you even start? And what is really behind the scenes of these places that, from the outside, seem simply perfect?
The truth is that over the years I’ve stepped into many of them, organizing tastings, sharing stories, pouring wines at sunset. But I’ve always done it from my side of the table, the wine side. I know how to create the experience once you are there, but I had never really explored what happens before that moment, everything that leads up to a stay that feels seamless and effortless.
Until a few days ago.
I met Annette Kelly here in Piombino, my little corner of the Tuscan coast that I call home, and what started as a dinner slowly turned into one of those conversations that you don’t want to end. As she began telling me her story, I realized very quickly that this wasn’t just someone working in villa rentals, but someone who had built her life around hospitality in a very deep and personal way.
Annette arrived in Italy in 1999 as a single mother of two, without speaking a word of Italian, making a decision that many people around her considered a little crazy. She moved her children into the Italian public school system and started building a life from scratch. Today, more than twenty-five years later, she smiles telling me that they probably feel more Italian than Irish, and you can sense the pride behind that journey, even knowing it wasn’t always easy.
Her path into hospitality came almost by destiny more than twenty years ago, when she started managing a large private estate hosting up to 24 guests, together with a smaller villa. Within a year, she knew she had found what she calls her calling, and what struck me the most while listening to her is that, even today, after all these years, she still speaks about her work with the same sense of joy and satisfaction.
Today she runs her business together with her son Scott, who has been by her side for over a decade, and there was something very natural in the way she described their relationship, how their different strengths come together and how much they genuinely enjoy working side by side.
As we kept talking that evening, over a seafood dinner that stretched into the night, it became very clear that although we operate in different worlds, we share a very similar way of looking at what we do. It’s about attention to detail, about caring for people, about creating something that feels personal and memorable rather than simply organized.
Because what Annette does goes far beyond renting a villa. She takes care of everything that happens before you arrive, and everything that unfolds during your stay. From managing properties for international owners to curating every aspect of the guest experience, from private concierge services to tailor-made itineraries that can range from vineyards and cooking classes all the way to helicopters and supercars, depending on what each guest dreams of.
At one point she said something that stayed with me: they love to make a wish come true.
And that is exactly where our worlds meet, because once you arrive in one of these villas, what truly makes the difference is not just the place itself, but what you experience inside it. A table set at sunset, a story behind a bottle, a moment that becomes part of your memory.
The next morning, sitting in front of a cappuccino before saying goodbye, we naturally found ourselves discussing how to bring these two worlds together in a more structured way.
So here is the simple part.
If you’ve ever thought about renting a villa in Tuscany, or even just felt curious about how it all works, now I finally know who to send you to. And on the other side, I’ll be there to take care of what happens once you arrive, the wine, the stories, the experiences around the table, what Annette beautifully calls “all about wine.”
To continue this conversation in a more open and relaxed way, we decided to do something together. We will host a live online conversation where we’ll simply talk through what it really means to rent a villa in Tuscany, sharing practical insights, timing, expectations, and also giving you a glimpse into what you can truly experience during your stay.
If this is something that has ever crossed your mind, you can sign up here. We’ll be live on LinkedIn, so you can and turn on notifications to join us live.
The conversation will also be available to watch later, so you can enjoy it at your own pace.
Who knows, maybe this is where your next trip to Tuscany quietly begins.
Thank you for reading and for being part of this journey.
Ciao,
Claudia 🍷
