Can you imagine a more romantic setting for a vacation than the scenic rolling hills of Tuscany? Divided by rows of arrow-straight Cypress trees and crowned with walled medieval towns, Tuscany is the place that inspires dreams and bucket lists. 

Of course certain hilltop towns in Tuscany can also be inundated with hordes of tourists that ruin the vibe, especially in summer. If you head to southern Tuscany, you can avoid the masses and experience the delights of the best Italian wine and food. But where to stay in Southern Tuscany is the question.

Wine tasting in Montepulciano, swirling and sipping the robust Vino Nobile while nibbling on local Pecorino cheese from Pienza and sampling some boar ragu with shaved truffles is a little slice of heaven. So where you stay depends on what you want to spend your time doing.

Volterra from the outer walls

Where to Stay in Southern Tuscany

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I consider Southern Tuscany as the area south of Siena, with the most well-known towns being Cortona (famous for its role in Under the Tuscan Sun), Montepulciano, Montalcino, Montefollonico, Monticchiello, and Pienza. Toward the coast, you will also find the hot springs in Terme di Saturnia, the bucolic Val D’orcia (Valley of the Orcia river), and the beach community of Maremma.

Here are a few suggestions of where to stay in Southern Tuscany that offer a variety of different experiences.

Locanda Rossa

Locanda Rossa pool

Perfect for a short stay for those that want to hit the beach and the hot springs after a busy few days touring Rome or Florence, Locanda Rossa offers a calm respite near the coast. This converted farmhouse and outbuildings offer luxury in a casual setting. Locanda Rossa offers farm-to-table dining, pasta-making classes with the chef, a spa and fitness room, a relaxing outdoor pool, and rental bikes for exploring the surrounding countryside.

Unlike other agriturismos in the area where the décor is a bit more farmhouse-rustic or thrown together from an assortment of old furniture, the rooms in Locanda Rossa have an elegant and luxurious feel. If you want more space and privacy, there are also stand-alone villas on the property.

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La Foce

La Foce Chiarentana building

If you want to stay in the Tuscan countryside, but be a little closer to small towns, La Foce is halfway between Rome and Florence, in the hills of the Val d’Orcia. The Val d’Orcia valley is a UNESCO World Heritage site and what every American thinks of when you say “Tuscany.” 

The Villa is an Italian Historic House surrounded by formal Italian gardens, which have become world famous. These romantic gardens are divided into geometrical patterns, with travertine stairs that lead to the rose gardens and a wisteria-covered pergola – perfect for romantic strolls. 

In addition to the main Villa, there are independent farmhouses and apartments – perfect for groups if you are traveling with friends or extended family. These allow you to have fun together but still enjoy some privacy. Many have private or shared pools as well. Just keep in mind that most will require a full-week rental.

The restaurant offers farm-to-table cuisine from its own vegetable garden across the road and estate-produced olive oil. Nearby you can enjoy Vino Nobile and Brunello di Montalcino from local wineries. 

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Follonico building with plants in pots

Ideal for couples, Follonico is romance personified with six stylishly designed suites set in a lovingly restored country house. Set among the vines, Follonico is a working agriturismo and the eggs you have for breakfast come from the chickens and the vegetables were fresh-picked from the garden. 

Laying in the sun at the pool, you can look up at the neighboring hilltop towns of Montepulciano and Montefollonico. I would highly recommend heading into Montefollonico for dinner and getting to taste hot pasta tossed in a giant wheel of Parmesan cheese at Ristorante 13 Gobbi.

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La Bandita Countryhouse or Townhouse

switchbacks on road leading up to La Bandita country house

La Bandita Countryhouse is located at the top of a hill at the end of a winding road that looks like something from a movie set. This luxury bed and breakfast offers either private rooms or can be rented out for an entire group if you are traveling with others.

The property is also home to working sheep farms, grazing on the surrounding green pastures, and looked over by adorable sheepdogs. The property features outdoor dining areas, guestrooms with sweeping views, and an infinity pool overlooking the Val d’Orcia.

And if you prefer to stay in town, the owner also runs La Bandita Townhouse in the center of historic Pienza, which also has an excellent restaurant.

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Airbnb in Montalcino

Where to stay in Southern Tuscany - View of hills near Montalcino
View from Montalcino Airbnb

If you are like me and prefer staying overnight in town after the day-trippers have left, consider renting an Airbnb apartment in Montalcino or one of the other small towns. Montalcino is a little further off-the-beaten-track than Montepulciano so you will find fewer tourists. In fact, when the sun goes down the town is quiet and it really allows you to feel like you are living like a local.

We really enjoyed our stay at the “Panoramic Nest in Montalcino.” This apartment sits right on the outer ring of the city’s walls and includes a terrace that overlooks the valley – perfect for enjoying a glass of the area’s Brunello di Montalcino.

What to do in Southern Tuscany

Visit Villages

Assisi St Francis cathedral and statue
Assisi cathedral

Whenever you are doing some slow travel in Tuscany, you will want to take day trips into the surrounding towns and villages to explore. Walking the cobblestone streets, poking down narrow alleyways, peeking into churches, and enjoying the views from the city walls are all part of taking a trip to Tuscany.

Of all my favorite Tuscan towns, Pienza in Southern Tuscany is one of the best. The charm has not been worn away by the masses. It is cute, clean, and the epicenter for Pecorino cheese. Unlike the salty Pecorino we are used to in the United States, you can find creamy young Pecorinos as well. 

Lunch at Podere il Casale

View of Pienza from Podere il Casale

Just outside of Pienza, on a farm overlooking the road made famous by the movie Gladiator, you will find Podere il Casale – and you may even encounter some friendly burros along the way. I would highly recommend that you make a reservation in advance for lunch or at least a cheese tasting. 

This organic farm also offers cooking classes, truffle hunting, and cheese-making demonstrations. The outdoor seating overlooks the valley with absolutely stunning views. You can take your time enjoying your food and wine, watching the farm’s peacocks strut past. 

Take a Wine Tour

roses at the end of the row of grape vines in a vineyard

Visiting wineries in Tuscany is not as easy as popping into tasting rooms in Napa. Tastings need to be prearranged and reserved in advance. Many wineries are located down winding dirt roads and can be hard to find using Google Maps. Really the best way to have a full day experiencing wine is with a wine tour. This is why taking a Tuscany wine tour is really the way to go.

We took a private wine tour with Tuscan Organic Tours and can’t recommend them highly enough. The owner, Giacomo, is tightly tied into the slow food and organic farming movement in Tuscany. Your tour will not just include wine tastings, but he will give you the history of the area and tell you more about the landscape and environment.

With so many choices for wine tasting, we told Giacomo what we liked and where we were staying, and he arranged a perfect day. We focused on the Montepulciano region and visited wineries both in town and in the countryside. He also taught us how to experience a vertical tasting to be able to differentiate between vintages. Lunch in a lovely restaurant in Montechiello was a bonus!

Tuscan Organic Tours also just introduced a new Biodynamic Brunello wine tour in Montalcino. This tour is perfect if you are staying in Siena or Southern Tuscany. They will pick you up at your accommodations and then head down to Montalcino.

The first stop is at Podere Le Ripi, a biodynamic winery, where you will explore the vineyards, and cellars, and finish off with a vertical terroir wine tasting. You will then continue to Molino di Sant’Antimo for a guided tour of the wine cellar followed by a delicious homemade lunch paired with a selection of wines.

After lunch, you will pay a visit to the famous Abbey of Sant’Antimo and then end the day with a visit to Montalcino for a short guided visit before returning to your accommodations.

Wine Tasting at Podere Le Ripi

Glenn holding wine outside of Podere Le Ripi

There are approximately 250 wineries in the small Montalcino wine region, producing the legendary Brunello di Montalcino, as well as the more affordable Rosso di Montalcino and other Tuscan blends. While all the wine regions in Tuscany use the Sangiovese grape, each region has its distinct varietals and in Montalcino, the Brunello is the cream of the crop.

It will be impossible to visit all 250 wineries, but I would recommend putting Podere Le Ripi on your list. Owned by one of the brothers from the famous Illy coffee family, this winery offers the best I have seen in terms of a tasting and tour experience. Reservations are required, as you will be appointed your own host for your tour and tasting, and I would recommend pairing it with their wine-tasting and lunch option. They bring in food from a Michelin-starred chef that is absolutely fantastic.

Looking for more options?:

  • Don’t overlook the wine regions of Piedmont, which makes an excellent and not as crowded romantic getaway in the Italian countryside!
  • If you prefer the French countryside, maybe one of the best towns to visit in the Languedoc region in the South of France would be a better fit
  • For a real splurge, a few days in Lake Como is the perfect spot to celebrate an anniversary or special occasion!

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