In a nutshell
- We researched dozens of wineries across Tuscany and picked the 6 best places to stay on a vineyard — every one of them has a great location and seriously above-average reviews.
- Our absolute favorite is Borgo Sant’Ambrogio — on its vast estate in the Val d’Orcia, you’ll experience Tuscany at its most authentic.
- The most affordable option is Fattoria di Capezzana, not far from Florence — we ate at the on-site restaurant ourselves and can absolutely recommend it!
Borgo Sant'Ambrogio Resort
The Borgo Sant’Ambrogio Resort is a large 17th-century wine estate on the edge of the Val d’Orcia, the most beautiful Tuscan landscape there is. We can’t recommend it enough for your road trip through Tuscany.
The estate is surrounded by about 125 hectares of land with oak forests, wheat fields, olive groves, and vineyards. It doesn’t get more Tuscany than this!
On the grounds you can enjoy wonderful walks and bike rides — rental bikes are available on the property.
There’s a really beautiful infinity pool, a restaurant serving the estate’s own organic produce, and you’re just minutes away from Pienza, one of the most beautiful villages in the Val d’Orcia and one of the most beautiful places in Tuscany altogether.
Book Borgo Sant’Ambrogio Resort
Capanna Suites
The Capanna Suites is also on the edge of the Orcia Valley. Here the focus is entirely on wellness.
Every room reservation automatically includes 1.5 hours in the wellness area, which you can reserve on-site. You’ll have the wellness area — complete with a whirlpool, sauna, and chromotherapy shower — all to yourself.
The hotel is just a stone’s throw from Montalcino, the home of one of Italy‘s most exclusive wines, the Brunello di Montalcino.
It’s also produced at Capanna Suites, and you can taste it in the on-site wine cellar along with other Tuscan delicacies.
Palazzo Massaini
At Agri Palazzo Massaini, also on the edge of the Val d’Orcia, estate wine has been produced for 800 years. You can also pick up a bottle in the winery’s shop.
Set on around 300 hectares of land is the medieval palazzo that houses the reception, and not far from it two typically Tuscan country houses with multiple rooms: La Pieve and Cavarciano.
We especially recommend a room in La Pieve: it has a pool with sweeping panoramas over the landscape, and just six rooms and two suites in total.
A true standout is the stunning cypress-lined avenue leading up to the palazzo — the perfect Tuscany photo!
Castello di Fonterutoli Wine Resort
For six centuries, the noble Mazzei family has been producing Chianti wine at Castello di Fonterutoli.
This is no ordinary agriturismo — it’s a medieval castle in the tiny village of Fonterutoli.
The 16 rooms and apartments are spread across several buildings throughout the village.
So you won’t feel like a typical hotel guest, but rather like a genuine resident of a charming Tuscan village in the Chianti hills.
There’s a small trattoria, a café, a wine bar, and of course the sprawling Fonterutoli wine cellar: free guided tours are offered where you can taste the Chianti Fonterutoli.
Salvadonica
The Salvadonica is just half an hour from Florence, right in the heart of the Chianti region.
If you want to spend several days exploring Florence during your stay, this is a seriously great base for that. That said, the nightly rate is on the higher end.
Salvadonica consists of several buildings dating back to the 14th century and produces its own Chianti Classico, as well as olive oil and fresh fruits and vegetables.
In addition to the minimalist-designed rooms, there’s also a restaurant, a tennis court, and an infinity pool.
Fattoria di Capezzana
If you’re looking to keep costs down, Agriturismo La Fattoria di Capezzana is a fantastic option. It’s located about 45 minutes north of Florence, and we’ve been there ourselves.
Because this Tuscany winery accommodation is not in the Val d’Orcia or the Chianti region, it’s much more affordable. The landscape here is hillier, but equally beautiful.
Wine and olive oil have been produced on the Capezzana estate for 1,200 years.
The real highlight of the property is Restaurant La Vinsantaia. It has an outdoor terrace with an absolutely stunning vista over the vineyards and olive groves. We’ve sat there ourselves and can highly recommend it!
