La Dolce Vita: A Step-by-Step Guide to Renting a Villa in Tuscany

IL CORNELLO is the villa my family and friends rented this summer. We booked it through Tuscany Now & More – they were great to work with and we would use them again. Il Cornello is a centuries old former convent transformed into a nine bedroom luxury villa. All of the bedrooms had their own bathrooms except one that was right next door.

It may sound overwhelming to think about booking a villa in Tuscany for a family vacation, and that’s because it is.

Planning a trip like this requires a LOT of work…in my case, it took three years of planning although that was mainly thanks to Covid cancellations. However, even with those cancelled trips that bought us a lot of extra time, I continued to work on it month after month to make sure we had a successful trip for my group of 13 family members and friends that feel like family, with ages ranging from the mid 70s down to age 10.

We needed to make sure there was something for everyone! I think my planning paid off – I for one had an amazing time that I will never forget but I do credit a lot of that enjoyment to planning ahead.

You will never regret going to Tuscany – it is one of the most beautiful, inspiring places I have ever been and I really want to go back – something that I don’t often say.

Here is what I learned that I hope will be useful to you.

Note: I plan to feature the towns we visited, our activities (bike tour, wine tasting, etc), stand out restaurants and other details about our trip in a future post. Also there is a lot of information on my Instagram feed from our trip if you are looking for specifics.

And P.S. If you are enjoying this newsletter I hope you will forward it to others who have a love of all things travel with the occasional shopping suggestions.


We rented our house through a company called TUSCANY NOW & MORE. They have lots and lots of properties to choose from in all different areas of Tuscany and Umbria. I had a great experience working with them – their agents are very responsive and helpful and they stuck with us through two years of covid cancelled trips without raising the rates or charging us a cancellation fee. Even if you don’t plan on going to Tuscany in the near future but would like to go someday, you should sign up to receive their emails because they feature a different property or experience in each email. It is fun to look at all of them, watch the videos, and get a sense of where they are and what they offer. Most villas have concierge and housekeepings services as well – which is huge when you are flying blind as we were.


  • Pick your LOCATION – Tuscany and Umbria are very large regions of Italy – see the map below. Consider that certain villas may be remote and difficult to get to a town or village for essentials – it is important to think about what you want when booking. For example, do you want to be able to walk to a village? How far is the house from Rome? Florence? Distance to the closest grocery store? Some of the stores in the smaller villages do not open on Sundays so you will want to plan around that as well. There are certain details that the rental websites don’t mention that you may not think to ask so best to get all the information that you can up front.
  • Book a LOCAL TRAVEL AGENT – I used the wonderful Lucia Norrito with Tuscany Slow Travel. Words cannot convey how invaluable she was on our trip. She held multiple calls with me before our trip, made recommendations based on our group, and put together a daily itinerary for us.
  • TRANSPORTATION IS KEY: Book rental cars WELL in advance and (important!) you need to specify automatic cars which can sell out quickly in the summer months so book early. All of this planning requires a lot of back and forth so I cannot overemphasize the need to plan ahead. I would also suggest renting two cars for your group so that everyone has some independence if they want to do different things during the day.
    • Go to AAA and apply for an international drivers license – these are required to rent cars in Italy. It is an easy process but again, just one more item on the to do list that you will want to handle and cross off.
    • Be prepared for rough terrain getting in and out of your villa (this was the case with our villa — information we learned from the travel agent, not the website – they won’t tell you that!) and around Tuscany – you will likely want to book an SUV, especially if you have a larger crowd.
  • Make sure you check the AIR CONDITIONING situation – not all Tuscan villas are equipped with whole house A/C or in some cases any A/C — reach out to the villa rental company for a discussion on how the house is equipped (or not equipped) with air conditioning. I would recommend a “whole house” A/C if you can find it because it can get HOT in the summer. For those of you without restrictions on when you travel, I can only imagine that the Fall is the most beautiful time of year in Tuscany, and you wouldn’t have to worry about the A/C.
  • Double check the NUMBER OF BEDROOMS that come with the house – depending on your rate, you may be restricted from using all the bedrooms in the house. Although we didn’t need all of the bedrooms in our house, we opted to book the whole house because I didn’t want the stress of telling the kids not to go in this room or that room.
  • Choose a villa with a POOL, especially if you have kids with you. (And by the way, if you’re traveling with kids be sure to pack UNO, a football (boy moms are never without one), goggles, small pool toys, crafts, and other activities to keep them entertained.)
  • Choose a villa that has an option for HOUSEKEEPING AND CHEF SERVICES, and if you need it, babysitters – after a long day of sightseeing, you will want not want to cook or do laundry. The best thing after a day in Tuscany is coming back to the villa, opening up a bottle of wine, and having a delicious Italian meal. We used the villa housekeeping and cooking services several times on our trip. It was especially nice the first day we arrived and the day we traveled to Florence not to have to lift a finger. We also booked a babysitter to go out to the most magical dinner – more on that later.
  • Pre-order GROCERIES – traveling to Tuscany can be tiring. Make sure you have pre-booked the essentials such as breakfast, coffee, snacks, laundry detergent, and the most important essential: alcohol, so it is waiting for you when you arrive.
  • Schedule ACTIVITIES: As beautiful as the villas can be, you do not want to sit around all day. Be sure to check out the various towns and villages, tours and guides for the larger cities like Rome and Florence, bike tours, dinner reservations, car services – I refer you back to the local travel agent suggestion, as they can help you with all of this.
  • Set aside plenty of time ahead of your trip for FORMS, FORMS and more FORMS. Our villa required many forms as did the Italian government and the rental car company. None of them are difficult; just time consuming.
Italy is My Boyfriend, by Annette Joseph: I loved this book written by American author, influencer, food stylist, among other things, Annette Joseph, about her adventures in Tuscany while trying to purchase a second home. It is SO entertaining – I could not put it down.
The Val d’ Orcia is classified by UNESCO as a world heritage site and many claim these to be the most beautiful landscapes of Tuscany; these are best enjoyed from the pool or it’s adjacent shaded seating area. In true Tuscan style this breath-taking villa is set on a hilltop with a private cypress-lined access road, offering spectacular views of the unspoilt countryside – these very views have been long-standing favourites amongst Hollywood directors and seasoned writers searching for special inspiration. 
Here is our lovely local tour guide, Lucia, with Tuscany Slow Travel. She met us for lunch the first day and answered all of our questions (we had many), gave us tips and suggestions for the week, and finished planning the final details of our visit. She also stayed in touch with me the entire week, offering suggestions and answering questions like how far is to so-and-so? Is this town worth visiting? Where should we eat lunch? And on and on. I do not know what we would have done without her. She was so patient, kind and knowledgeable.
Lucia’s town of Sarteano
A fortress near our villa.
The view from the top.
Sightseeing in the village on the first day.
Lots of time was spent out here by the pool
Gifts from the villa owner.
The lovely housekeepers prepared this delicious spread for us the afternoon we arrived. (Not pictured: voluminous amounts of Italian wine.)
Patio on the other side of the house looking out at the tennis courts.
Thinks he’s Italian
Also thinks he’s Italian.
Simple but lovely bedrooms, most of them with beautiful views. All the bedrooms have their own bathrooms except for one and it is right next door.
Extra hang out room for the boys.
Pizza night.
The Chef got a few slight burns in the process.
Pizza Oven
Our Pizza Chef
Post-pizza swim
Coffee essentials.
Three sets of twin beds for kids and singles.
After dinner card games on the patio.
You could also play pool, tennis or ping pong.
That’s Amore. ❤️

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