Italy is my favourite country in the world. And if there is one region that helped cement this in my mind, it’s Tuscany. When it comes to choosing the best places to stay in Tuscany, it can be difficult to know where to stay.
Tuscany is every bit as dreamy and beautiful as you could imagine it to be. Think medieval hilltop towns, lush vineyards, friendly locals and delicious wine.
It’s a place I keep finding myself coming back to, for good reason. It’s an expansive area – about 23,000 square kilometres in fact – with so many villages and towns to visit. As soon as you’ve been hit with the Tuscan travel bug, you’ll find more and more places to add to your wish list.
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Hire a car
If time and budget permits, for your first trip, we recommend staying in Florence and at least one other town. This will give you a true sample of Tuscany.
Compare prices from all major car hire companies with SkyscannerMake sure you hire a car. This lets you zip around the countryside and enjoy the freedom of exploration and ensures you can choose any of the places to stay in Tuscany that you wish. Not just the ones near a train or bus station. I’ll never forget our first trip around Tuscany driving our trusty little Fiat 500. We’d have the top open, navigating tight country lanes and the most gorgeous green vineyards rolling out in front of us. I felt so alive.
Driving in Italy can be a little different to home. Before you head off, check out our driving in Italy guide with our top tips for a safe and enjoyable trip.
Now, where should you stay in Tuscany? It can be overwhelming with so many available options. To help you plan that dream trip, here are 5 tried and tested places to stay in Tuscany.
Agriturismo experience in Val D’Orcia
The Val D’Orcia region is known for its rolling hills, cypress trees and medieval hilltop towns. It’s the picture perfect image you’ve conjured up in your mind and the epitome of Tuscan charm. It’s no wonder this whole area has UNESCO World Heritage status.
The hilltop towns of Montalcino and Pienza are probably the most well-known and visited villages. As you’re driving through the hillside, nothing will prepare you for your first view of these mighty towns in the distance. Once there, you can spend hours wandering the cobbled streets, as church bells ring out and the scent of freshly cooked Tuscan pici pasta wafts through the air. You’ll be hard-pressed to resist the multitude of wine bars, serving the world famous Brunello.
Podere Spedalone
With beautiful views to be enjoyed, you’ll want an amazing place to match. Look no further than Podere Spedalone. Being an agriturismo, it sits within a working farm complete with crops and farm animals. You’ll be staying in a building that is nearly 1,000 years old.
The rooms are rustic yet comfortable. You can enjoy complimentary aperitivo whilst the sun sets across the valley. What better way to end the day than washing down a stunning wine with some cured meats, local cheeses and fresh mini pizzas?
For dinner, there is no need to drive into town. You can enjoy a home cooked meal which we imagine is exactly like our non-existent Italian Grandmother would have made! For an additional €35 per person, a 4 course Italian feast is offered. Of course, all the fresh ingredients come from the farm. Sitting around the long family table, you’ll enjoy sharing stories of your adventures with other guests. You’ll munch down on some of the best Tuscan food you’ll find.
After dinner, the cooks might even enjoy a bottle of wine with you, giving you insight into the local way of life. It feels like a family away from family. It’s such a great destination to immerse yourself in Tuscany.
Deluxe B&B in the Chianti region
The Chianti region is famous for its namesake wine. Located close to Florence, it’s an easy and delightful area to visit. Full of lush vineyards, forest areas and gorgeous small towns, it’s a picturesque area made for exploring.
Chianti was the first area we visited in the Tuscan countryside, and is what had us coming back for more. Towns like Castellini, Greve and Radda in Chianti each have their unique charm. You’ll experience so many memorable moments. You might spot a red Vespa lined up against the most beautiful rustic door frame creating the perfect picture. Drop into a vineyard or two to try the famous Chianti Classico. Or, spend a few hours learning the art of Italian cooking from some locals.
Looking to add more things to your Italian bucket list? Check out our 50+ things to add to you Italian bucket list.
La Locanda
Whilst you could choose to stay in the centre of one the towns, our recommendation is a deluxe B&B in the countryside. La Locanda is a 10 minute drive outside of Volpaia, a super small yet gorgeous village. It’s the perfect combination of being one of the best places to stay in Tuscany, and being something a hidden gem.
La Locanda is owned by Guido, a Roman who fell in love with Tuscany. He turned a run down farmhouse into a deluxe B&B with all the creature comforts of the modern world. You won’t run out of options for things to do in the surrounding area. Guido is the perfect host taking you through countless activities and road trips. The aperitivo in the afternoon is a real treat, with complimentary wine and snacks. The views are sensational, as you look out across the woods and see the towns of both Volpaia and Radda.
For dinner, you’ll find a few sensational restaurants in the nearby town of Volpaia. Guido will look after a booking for these and let you know what’s best to try on their menus too.
Agriturismo charm in San Gimignano
San Gimignano sits firmly on the tourist trail in Tuscany. Medieval towers dominate the skyline, it’s no surprise it was known as the Town of Fine Towers. In fact, between the 11th and 13th century, we learnt that there were as many as 72 towers across the skyline. That would have been quite a domineering sight back in the day!
Today, only 14 towers remain, but it still bodes for fascinating viewing. A UNESCO world heritage site, San Gimignano is located halfway between Florence and Siena. It also lies on the old pilgrim route of Via Francigena, which connects Canterbury to Rome. And before you ask about that route- we haven’t done it, but we’ve read many people enjoy the pilgrimage every year!
Torraccia di Chiusi
Torraccia di Chiusi is a great place to stay close by to San Gimignano. Located in the countryside, it has an amazing view back towards all those towers. The family country house will feel more like home once the owner, Donatella, takes you through the buildings and grounds. In a building more than 1,000 years old, you can feel the history all around you. They produce their own wine and olive oil on site, so you’re surrounded by stunning greenery and vineyards.
Like the properties above, they offer complimentary aperitivo with their local wine. For dinner, they serve up a delicious 4 course dinner for 25 euros each. This agriturismo is also located 40 minutes to Siena, so you can use this as a base for more day trips too.
The ultimate in Tuscan luxury
We enjoyed staying in each and every of the aforementioned places. They’re amazing, with wonderful staff and a ‘real’ Tuscan feel. If you want to take your Tuscan holiday to the next level of memorable, you’ll want to visit the town of Chuisdino. You can even adopt your very own Nonna like we did!
Borgo Santo Pietro
Jeff booked us a few nights at Borgo Santo Pietro to celebrate my birthday, and boy did he do well! Sometimes in life, you need to treat yourself, and this was a total ‘treat yourself’ moment. Of all the places to stay in Tuscany, this was totally next level.
Upon arriving up the perfectly manicured driveway, the first thing you’ll likely find is a car park full of luxury cars. If you’re like us, you’ll park your little Fiat rental between a Tesla and a Porsche. If this isn’t your usual scene, don’t be dissuaded. The staff here will treat you like royalty.
The property is made up of the main building and some surrounding villas. There’s a variety of options to suit your budget (admittedly the cheapest room is still way well above our usual standard).
The communal areas are something straight out of a Vogue magazine. Antique furniture together with fresh vases of flowers adorning every room make for a quaint setting. The sweet smell of lavender will follow you around everywhere.
Borgo Santo Pietro has so much to offer on the grounds, you don’t need to leave. There is a stunning infinity pool looking out towards the countryside. You could lay there all day and not tire of the view. There’s a cooking school, an artist in residence for all your painting school needs, and an on-site florist. These are a sample of the activities you can avail yourself of.
To top everything off, there is a Michelin star restaurant right on site. That’s right, you can dress up for an evening of utter foodie joy, and then stumble back to your room after a few glasses of Tuscany’s finest wine.
If you do find yourself wanting to step outside the gates, there are some great attractions nearby. The Abbey of San Galgano is a few minutes down the road. Here you’ll find the roofless remains of a 13th-century church. And if you’re in season, sunflower fields adorn the area. It makes everything even more beautiful.
Rooftop views in Florence
Florence is a must-visit destination for your first visit to Italy. There’s a reason that millions of tourists flock to this city every year. There’s a long list of must-do’s. The Duomo is an imposing building that is magnificent both inside and out. You must visit the Uffizi Gallery, to see works by Leonardo da Vinci and Michelangelo. Ponte Vechhio is the famous bridge. Finally, visit the Galleria dell’Accademia to see the statue of David.
However, in the peak seasons (July and August especially), it is bursting at the seams. Even in the shoulder seasons, it’s still very busy. And that even takes into account that there are more places to stay than anywhere else in Tuscany. To make the most of your time there, stay in the centre of the city. This is what I recommend for Venice too. You give yourself the best chance to get to the main sites as early as possible before all the day trippers arrive. In the evening, you can also experience the Italian way of life in a local piazza that isn’t buzzing with tourists.
Antica Torre di via Tornabuoni
Antica Torre di Via Tornabuoni is a wonderful place to stay in the city centre. The main drawcard for this hotel is the rooftop terrace that has a perfect view of the Duomo. It’s the perfect place for an afternoon aperitivo with an Aperol Spritz or two.
The location is fantastic too, it’s right on the river and an easy walking distance to most attractions. It’s also a short walk to the train station when you’re commuting.
Other tips to make the most of your Tuscany trip
- Whilst there are some towns you could commute to via train, I recommend hiring a car whilst you’re touring the Tuscan countryside. You should avoid having a car in Florence, given the city is within a limited traffic zone. If you need to pick up or drop off your rental, considering hiring it from the Florence Airport branch. Do this even if you have no reason to go to the airport (eg. Your inbound/outbound journey is via train). The airport is right near the main motorway taking you to the Tuscan countryside. You’ll have a much less stressful experience than if you book in central Florence and need to navigate those streets.
- A small car is worth considering. Tuscany is full of tight country lanes.
- Siena is definitely worth a visit. The Piazza del Campo is a famous square, which also holds a horse race twice a year. We have never stayed in Siena, opting to commute from the countryside for day trips. This has suited us well.
- The Leaning Tower of Pisa is also within Tuscany. It’s worth a quick stop to marvel at this structure (and be sure to get a few funny photos also). It’s just over a one hour drive from San Gimignano.
- If you’re not convinced with these options, find more places to stay in Tuscany at booking.com.
If you’re heading to Tuscany, why not explore more of Italy? It’s our favourite country in the world and the opportunities for exploration are endless. Read our other Italian articles here:
Want to eat at the world’s best restaurant? Find out what it’s like to dine at the world’s best restaurant.
A food lover who enjoys a city stay? Check out our 3 days in Bologna itinerary
.
Something by the sea? Read about our one week in Puglia.
Don’t forget the classics like Venice. We’ve got you covered with our best Venice recommendations too.
What do you think of our best places to stay in Tuscany? Have we missed your favourite? We’d love to hear below!
I love reading your adventures. So many wonderfully inspirational stories to inspire adventure!
Thanks Mave! Glad to have you along for the adventures!
These are gorgeous!!!! I love Italy however I haven’t explored it as much as I would love to. The three nonnas are too cute! 🙂
They were our favourite people we met in Tuscany. Just so giggly and content sitting outside watching the world go by. And so, so cute!
Just a question…”Why is it that Tuscany it’s always shown with Hills and Country…
What about our Beautiful Beaches???
We are full of the Mediterranean Coast!!!
Ok just wanted to ask…Thank You and
Buona Visita🌻🌻🏊🏖️🚣🚵⛷️🏞️🏔️🍷🍾
A very good question indeed! And I’ll try and answer it from our perspective, although it may not be true for all! When we’ve ever thought of Tuscany, it’s images of fantastic wine and a laid back country environment. Maybe that’s by having a Tuscan wine on the table at home in Australia? Or the way it is depicted in movies? For two Australian travellers however, the rolling hills of Tuscany are unlike anything we have at home. We have some great wine areas, but nothing like Tuscany. In fact, Margaret River here in Western Australia has some great wines and also has some magnificent beaches! So maybe it’s not even just a Tuscany issue 🙂