Vignalsole, Radda in Chianti, Italy (Vrbo): We don’t like to stereotype any destination, but there are certain things that inevitably come to mind—things a traveler hopes will come true—when planning a holiday in the Tuscan countryside. Olive groves, vineyards, historic towns paved with cobblestones, and old stone houses are key among them. (We like to blame Under the Tuscan Sun for these clichéd expectations.) Luckily for us, when it comes to Vignalsole, all of these dreams can come true. This home not only ticks off every one of those boxes, but it also offers much more for any poor soul desperately in need of a summer vacation.
We’re pretty sure these are the views Leonardo da Vinci enjoyed in his childhood, ones that, if we may be so presumptuous, inspired the backdrops of his many fine ladies. Those women may have had gorgeous jewels, fancy frocks, and ermines, but only a modern Italian noble—or a traveler playing one—gets the luxury of frolicking in this pool during a hot summer afternoon.
Vignalsole is located just outside of Radda in Chianti, the seat of the Chianti wine region. Connection to the area’s renowned vino is one you should definitely exploit, just as the village did when it decided to change its name in 1911 from the simple, but wine-less “Radda.”
If you’re like us, you keep a running count of all the spaces where you can drink and dine en plein air when deciding which home you will rent for your next vacation. We’re only at the fourth photo, and the count is already up to 2.
If you couldn’t tell from this image, what you are looking at here is a genuine, 100-percent stone house. It’s a luxury generally only found in noble, old structures and one that Vignalsole takes to the extreme, with a rosemary bush-bedecked stone wall also circling the property.
May we present the third spot for enjoying an aperitivo outside. Thanks to these tall cypresses, this one offers some privacy and a little shade that is still on point with the very Tuscan theme. (Cypresses are almost synonymous with Tuscany at this point.)
Imagine all the gorgeous pastas and buffalo mozzarella salads you’ll whip up here—enough to convince you that you may just have a career as an Instagram food influencer. While even diva influencers must clean up after themselves or risk their mammas running after them with a wooden spoon, you should also make note that the house does come with a housekeeper to help ensure things stay in tip-top shape.
While this home isn’t as old as the region’s first settlers, who landed in the area as far back as 2,000 B.C., it still has plenty of wisdom in its historic walls. It has recently enjoyed a modern restoration, but the listing agent ensures that none of the “ancient features” of the home were changed.
Welcome to where you will eat for dramatic dinners when you want to pretend you are ruling over your very own ducato.
There are five bedrooms and four full baths in this home. What you do next depends on whether you’re more of the “let’s pack them all in” or the “I need to repair to the Italian countryside…alone” type. If the former, rest assured that the home comfortably sleeps nine. If the latter, welcome to your palace where you may sleep in a different room each night.
In addition to having all the delights of the Tuscan countryside at your fingertips, Vignalsole is also a short drive away from Florence and Siena, as well as all of the charming little towns in between that most tourists never get the chance to visit. One of those is the medieval town of Radda in Chianti just down the road.
We are all about the summer vacations right now because this world needs one big collective break. But if you’re in fall-planning mode, you will be happy to know that vineyards effectively make a moat around this home, surrounding it with their gorgeous vines that put on a colorful display once the weather starts to change.
For centuries Radda in Chianti was caught between Florence and Siena, with both cities vying for control. May we suggest you embrace that spirit and fight for control of the best lounger and the best bottle of local wine by the pool?
This area of the country is all about the views, which is why, rather than being the first in the house to claim the biggest bedroom, you should race around to determine which room offers the best scene from the window and then call dibs.
Vignalsole is basically the perfect Tuscan villa. It’s nestled in the Chianti hills surrounded by cypress trees, forests, and the vineyards that produce some of the best wine in the country. If that isn’t a recipe for a vacation that will make it into the family history books, we don’t know what is.
Book Your Stay: Vignalsole, Radda in Chianti, Italy: $1,000/night via Vrbo