
When people hear that we travel to Tuscany twice a year to visit villas, the first reaction is usually, “What a tough job!” While there is certainly no shortage of stunning views, beautiful countryside and incredible villas, not to forget the wonderful food and wine, there is also a huge amount of planning and hard work that goes into making these trips a success.
At To Tuscany, our villa visits play an important role in ensuring we continue to provide the expert knowledge and personal service our guests value so highly.
At To Tuscany, our villa visits play an important role in ensuring we continue to provide the expert knowledge and personal service our guests value so highly.
The Planning Begins
Twice a year, usually in March and then again in October or November, we head off to Tuscany for a week of villa visits. Once flights are booked, the real work begins.
The first task is deciding which area of Tuscany & Umbria we will focus on during the trip. Accommodation for the team needs to be arranged and then a detailed itinerary starts to take shape.
Although the trip lasts five days, we do not conduct villa visits on our arrival or departure days. This means we have just three full days to fit everything in, typically visiting around 18 villas or hamlets during the week. Careful thought goes into selecting properties that team members have not seen before, helping everyone expand their knowledge of our portfolio and experience different areas of Tuscany.
Once the villa list is agreed, routes are carefully planned to minimise travel time and make the most of every day. Our Italian Owner Team then gets to work, contacting each owner or keyholder to arrange access and make sure someone is there to meet us, open the doors and show us around.
The first task is deciding which area of Tuscany & Umbria we will focus on during the trip. Accommodation for the team needs to be arranged and then a detailed itinerary starts to take shape.
Although the trip lasts five days, we do not conduct villa visits on our arrival or departure days. This means we have just three full days to fit everything in, typically visiting around 18 villas or hamlets during the week. Careful thought goes into selecting properties that team members have not seen before, helping everyone expand their knowledge of our portfolio and experience different areas of Tuscany.
Once the villa list is agreed, routes are carefully planned to minimise travel time and make the most of every day. Our Italian Owner Team then gets to work, contacting each owner or keyholder to arrange access and make sure someone is there to meet us, open the doors and show us around.

Preparing for the Trip
Before we even set foot in any villa, there is plenty of preparation to do.
Each villa has its own information sheet, allowing us to check that all the information displayed on our website remains accurate and up to date. We review any issues that may have arisen during the season and ensure they have been addressed. Floor plans are also checked against our descriptions so that guests receive the most accurate information possible.
By the time we set off, every member of the team is equipped with detailed notes and ready to put their detective skills to work.
Each villa has its own information sheet, allowing us to check that all the information displayed on our website remains accurate and up to date. We review any issues that may have arisen during the season and ensure they have been addressed. Floor plans are also checked against our descriptions so that guests receive the most accurate information possible.
By the time we set off, every member of the team is equipped with detailed notes and ready to put their detective skills to work.
Life on the Road
Once in the area, we travel between villas in the trusty To Tuscany van, driven by one of our Italian colleagues who knows the region like the back of his hand.
At each villa, we are welcomed by an owner or keyholder who guides us around the property and answers any questions we may have. This is our opportunity to verify every detail, from bedroom layouts and facilities to outdoor spaces and special features that may not always come across fully on a website.
Of course, we also take plenty of photographs along the way. Not only do they help us update our records, but they also provide the wonderful content you often see on our social media channels.
While the days are busy, there is still time to enjoy one of the many perks of being in Tuscany. Evenings are often spent sharing delicious local food, whether that's a plate of homemade pasta, a traditional pizza or a glass of Tuscan wine while discussing the day's villa visits. These moments are a wonderful chance for colleagues to come together, swap stories and strengthen the teamwork that helps make To Tuscany what it is.
At each villa, we are welcomed by an owner or keyholder who guides us around the property and answers any questions we may have. This is our opportunity to verify every detail, from bedroom layouts and facilities to outdoor spaces and special features that may not always come across fully on a website.
Of course, we also take plenty of photographs along the way. Not only do they help us update our records, but they also provide the wonderful content you often see on our social media channels.
While the days are busy, there is still time to enjoy one of the many perks of being in Tuscany. Evenings are often spent sharing delicious local food, whether that's a plate of homemade pasta, a traditional pizza or a glass of Tuscan wine while discussing the day's villa visits. These moments are a wonderful chance for colleagues to come together, swap stories and strengthen the teamwork that helps make To Tuscany what it is.
Back in the office
We return with pages of notes, hundreds of photographs and lots of new information, all of which needs to be carefully updated across our systems and website.
Every visit gives us a deeper understanding of the villas we offer, helping us provide honest, personal recommendations to our guests. When a customer asks about a particular property, there is a good chance that one of our team members has stood on its terrace, explored its gardens or admired the view from its pool.
Every visit gives us a deeper understanding of the villas we offer, helping us provide honest, personal recommendations to our guests. When a customer asks about a particular property, there is a good chance that one of our team members has stood on its terrace, explored its gardens or admired the view from its pool.

Why It Matters
These villa visits are one of the things that make To Tuscany different. Rather than relying solely on photographs and descriptions, we invest time in seeing our properties first-hand and building strong relationships with owners and local teams.
Yes, there are long days, detailed checklists and plenty of miles covered, but there is also something very special about experiencing our villas in person. The knowledge we gain allows us to offer genuine, informed advice and helps ensure our guests find the perfect villa for their Tuscan holiday.
And while we are hard at work, we certainly cannot complain about the office views! ️
Yes, there are long days, detailed checklists and plenty of miles covered, but there is also something very special about experiencing our villas in person. The knowledge we gain allows us to offer genuine, informed advice and helps ensure our guests find the perfect villa for their Tuscan holiday.
And while we are hard at work, we certainly cannot complain about the office views! ️
"Every villa has a story, and our visits help us tell it."
This article was written by To Tuscany to help our guests have the best possible experience during their stay in Tuscany. Explore our entire selection of villas or contact our holiday home specialists, who are happy to assist you.
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