Celebrating 25 Years of To Tuscany

In 2025, To Tuscany celebrates a significant milestone: 25 years of helping guests discover the authentic heart of Tuscany through carefully curated villa holidays. What began as a bold decision to embrace a new life in Italy has grown into a respected and trusted villa rental agency built on the principles of personal care, reliability, and a deep love for the region.

A Journey Rooted in Passion and Place

The story of To Tuscany starts with its founder, Sean Caulfield. In the late 1990s, Sean moved from the UK to Tuscany with his Italian wife, leaving behind a business and home to start afresh in the Chianti countryside. Raising their three children there and becoming part of a close-knit community gave Sean an intimate understanding of what makes Tuscany so special.  

“Living in Tuscany has been a lifelong education in the art of living well, through food, wine, language, community, and nature. The values I discovered here, of balance, beauty, and meaningful connection, are the same values I have always tried to bring to To Tuscany.”

This inspiration led to the creation of To Tuscany.

“To Tuscany started with a dream. While I learn't Italian, we stayed at a friend’s cottage in the Chianti hills and fell completely in love with the place. There was something magical about the landscape, the people, and the pace of life. We knew we had found something worth sharing.”

And so, the journey began, starting with the transformation of a restored winery into a welcoming villa. From the beginning, the mission was clear: to offer more than just a villa stay but to create meaningful, memorable holidays rooted in authenticity and great service.

Innovation and Resilience Through the Years

Those early years brought both challenges and opportunities. When online travel booking was still in its infancy, To Tuscany was among the first in the industry to launch an online platform with real-time calendars, setting a new standard for transparency and efficiency. Then, as the Euro was introduced in 2000, To Tuscany expanded its reach across Europe, adding multilingual support and building a strong presence in Germany, France, the Netherlands, and beyond. Today from our UK base, we’ve used that experience to grow into a multilanguage global agency recognised for excellence in customer care, with systems built entirely in-house and refined over two decades of experience.

Over the years, certain moments have defined the company's character, none more so than the pandemic. Working closely with villa owners, the team ensured guest bookings were re-arranged and handled with empathy and fairness. This period deepened the trust between To Tuscany and its partners, reinforcing a sense of shared purpose and resilience.

Looking to the Future

Today, the company continues to prioritise the needs of modern travellers. Recent developments include the upcoming launch of a new website and more flexible booking options, reflecting changing habits and a growing demand for adaptability. 

“We've grown, adapted, and made plenty of mistakes along the way, but always with the goal of doing better.”

Yet, To Tuscany's ethos remains unchanged: to provide beautiful, high-quality villas in inspiring settings, supported by personal service and expert local knowledge.

A message from Sean Caulfield

"Thank you to our loyal guests and villa owners. Your support and feedback have shaped us. To those discovering us for the first time, we look forward to welcoming you. We promise a beautiful stay deeply rooted in a place we love and know by heart."