Best Places to Stay in Tuscany for Wine Tasting

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Tuscany is quite a large wine region that extends from north of Florence down to Lazio in the south. It encompasses many medieval hillside towns and hamlets with dozens of fantastic wineries to visit along the way. 

Where to stay is a big decision. There are hotels, agritourism farms in the countryside, unique villas, and boutique hotels dotted throughout the area. These are the best places to stay in Tuscany.

» You will love these 18 Beautiful Towns in Tuscany and 14 Montepulciano Wineries to Visit in Tuscany.

Siena Tuscany Italy - best places to stay in Tuscany

After visiting the area many times, we’ve found some really lovely options that we recommend staying at when you’re visiting Tuscany for wine tasting.

All of them are affordable luxury and offer all the amenities you expect from this level of accommodations.

If you’re hitting up Italy as part of a larger trip to Europe, be sure to check out our 2-week Europe Itinerary.

Planning for an Italy wine trip? Here's more

Tuscany Villas

⇒ Looking for the perfect villa with the exact amenities you need? Try’s list of fantasic villas. You can filter and search to find your perfect villa.

A lot of visitors to Tuscany have a dream of staying in a villa in Tuscany. It’s something like a required activity.

If that’s the case, you won’t have a hard time finding a Tuscan villa. There are many prestigious estates throughout Tuscany that have been converted into vacation homes.

In many cases, these were family homes passed down through generations. They still have all the charm and rustic characteristics of the quintessential Italian villa.

Whether you’re looking to rent a villa for your entire family – to suit a family reunion, a summer holiday for your children, or just as a sprawling place to spend a few weeks of vacation in Italy, there is a villa perfect for you.

You’ll just need to decide if you want to rent the whole villa, or go with more of a bed & breakfast style where the owners are still around to help with planning and feeding you.

Agriturismo Ca 'di PesaLEARN MORE

When you’re in Tuscany for wine tasting, it’s only appropriate to stay in an agriturismo with a surrounding vineyard, winery, and cellar. This is a 2-bedroom self-catering accommodation with free WiFi, a balcony and a terrace.

The apartment at Ca di Pesa is located just 5 miles from Greve in Chianti, affording you easy access to all of the wineries of Chianti. The top features of the apartment are:

  • Location, location, location.
  • Kitchen with refrigerator and kitchenware.
  • Peaceful, tranquil environment with privacy.
  • Located on a working vineyard – wine tasting is available to book.
book here

Villa Medicea di LillianoLEARN MORE

Villa Medicea di Lilliano is a luxurious villa located in the area of Grassina, just 8 miles from the Florence airport. You can rent one of the exclusive rooms in the villa, or even rent the entire 5-room estate.

It’s obviously really popular for weddings and events. But it’s also perfect for a relaxing vacation. The top features of the villa are:

  • A garden and a terrace, plus free WiFi
  • All units come with a patio, a kitchen with dishwasher, an oven, coffee machine and kettle.
  • A continental breakfast is served each morning.
  • The villa has an outdoor pool.
book here


Villa Villa Lolù is a comfortable and relaxing retreat in Terranuova Bracciolini, which is a great central location for wine tasting in Tuscany. The house is decorated with traditional Tuscan decor and colors. There’s a lovely outdoor pool with lounge chairs and a great view. The top features of the villa are:

  • 4 bedrooms, 2 baths.
  • Kitchen with dishwasher, an oven, and BBQ.
  • The villa offers car rental service.
  • The owners are on site for any issues or to help with organizing.

book here

Tuscany Hotels

We usually prefer to stay in a Tuscany hotel when we’re in the area for wine tasting. There are some really fantastic places in Tuscany that offer great service, lots of amenities, and a central location from which to do wine tasting around the region.

We always prefer affordable luxury hotels with immense charm and that certain Tuscan feel, so that’s what you’ll find on this list – only the best Tuscany hotels at an affordable rate.

Villa Bordoni Luxury Boutique HotelLEARN MORE

The charming, upscale boutique hotel, Villa Bordoni is the perfect place to stay in Tuscan countryside because it’s tucked away in the hills on a beautiful property that really makes you feel like you’ve found a secret Tuscan hideaway, but it’s still close to the places you want to go.

Villa Bordoni’s accommodations are charming Italian rustic style. It feels like staying in a nice farmhouse. It’s cozy and comfortable.

Each room is uniquely laid out – no two are alike. They have a wonderful restaurant, beautiful landscaped grounds, a pool, and a cooking school. What’s not to love?

book here

Hotel Villa del Capitano Luxury Art & RelaisLEARN MORE

If you’re wanting to visit the wineries near Montalcino and Montepulciano, there’s no better location than the town of San Quirico d’Orcia. Our favorite hotel in the area is Hotel Villa del Capitano.

It’s a luxury boutique art hotel, just a block from the main town center. The hotel is very comfortable, with large, nicely appointed rooms and bathrooms. The staff is very helpful. We also highly recommend having dinner at the hotel’s nearby restaurant.

book here

Fattorio ViticcioLEARN MORE

Another accommodation option is to stay at a winery near Greve in Chianti. The location of Fattorio Viticcio can’t be beat, because it is so close to Greve, in case you want to enjoy a dinner or a wine bar in town.

You will also have a wine tasting included in your stay. Expect to find rustic vineyard charm.

book here

Castel Monastero HOtel & SpaLEARN MORE

Castel di Monastero

If you want to stay somewhere that gives you celebrity treatment and impeccable service, you must stay at Castel di Monastero, located in a 10th-century medieval hamlet.

The amenities are endless here, including a gourmet restaurant, tennis courts, cooking classes, luxurious rooms, a wine cellar and bar, full service spa, and a tea room.

Castel di Monastero is often fully booked, but there are other comparable hotels in the area to check out. You really can’t go wrong with any of these high-class hotels.

book here

Poggio Casciano

Ruffino Winery

Opening in March to guests, Ruffino Winery offers unique accommodations in their Poggio Casciano renaissance estate. It’s everything you want from a stay in Tuscany.

The views are incredible, the estate is incredibly – it feels a bit like staying with a member of the royal family. They have a pool for guests, an outdoor terrace where breakfast is served, and a sprawling estate vineyard.

Perhaps best of all, the location is perfect, just a 30-min drive from the Florence airport, and a great launching point for the rest of Chianti to the south.

⇒ Contact Ruffino Winery for information about the opening and to book a stay.

Tuscany Farm Stays

Along the lines of a villa, Tuscan farm stays are a popular accommodation type. A farmstay can be quite luxurious and relaxing. For a list of great Tuscany farm stays, check out the information available from If you’re wanting to get a true feeling for how it is to live in Tuscany, these are the best places to stay in Tuscany.

farm stays

How Many Days in Tuscany Is Enough?

Tuscan Countryside view of Villa

To fully appreciate the wine culture and indulge in tastings without feeling rushed, we advise you to dedicate at least 3 to 4 days to the region. This timeframe allows you to explore the famous wine-producing areas, such as the Chianti Classico region and Montalcino, and visit several wineries.

This timeframe also allows for a more relaxed pace, enabling you to enjoy leisurely meals paired with excellent local wines and perhaps even participate in wine-related events or festivals that may be taking place during your visit. Ultimately, the specific duration depends on your personal preferences and how deeply you want to delve into the world of Tuscan wines.

Frequently Asked Questions on Where to Stay in Tuscany

Are there budget-friendly accommodation options in Tuscany?

Renting a villa provides a more private and immersive experience. Villas often come with stunning views, private pools, and the opportunity to experience the Tuscan lifestyle in a relaxed setting.

Can I find luxury accommodations in Tuscany?

Tuscany boasts luxurious villas, boutique hotels, and upscale resorts. Cities like Florence and Siena are known for their high-end accommodations with exceptional amenities.


These are some of the best places to stay in Tuscany. Depending on the exact location you wish to be in, you can choose one of these great options for your next Tuscany trip and be sure you’re getting great value and a comfortable stay.

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Best Places to Stay in Tuscany for Wine Tasting

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