Where To Stay In Tuscany? Top 6 Places To Consider.

Tuscany is one of the best, most romantic places to stay in Italy. It’s got the enchantments of Florence, gorgeous rolling wine country, and even seaside resorts. There really is so much to choose from when it comes to where to stay in Tuscany, which is why we’ve written this post to try and help you out!

Tuscany is easily one of our favourite places. Not just because we love the vino (and how affordable it is) but also because it’s home to utterly incredible architecture, like the Duomo in Florence and the Leaning Tower of Pisa. 

The best area to stay in Tuscany depends a lot on whether you’re a history buff, a connoisseur of local produce, or somebody who craves the sanctuary of untouched nature. To try and help you narrow down your options, we’ve summarised what we like best about 6 different parts of the region, each one offering a slightly different experience under the Tuscan sun.

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Important Considerations For Choosing The Best Place To Stay In Tuscany

Before we deep dive into the best areas to stay in Tuscany, here are a few points to keep in mind before booking a hotel or a B&B:

• Are you travelling with or without a car? It’s much easier to stay in a big city like Florence that has good transport links if you’re not planning on renting a car in Tuscany. If you are planning to hire a vehicle, you’ll probably find better deals and more tranquil accommodation in the countryside.
• Do you want to stay in a hotel or an agriturismo? Hotels are generally found in cities and come with more mod cons and in-house amenities. Agriturismo places tend to offer more authentic rural experiences (often on a farm) but with fewer services.

• How many days do you have? I recommend 7 days. This will give you more time to travel around and open up your accommodation options. If you only have 3 days, I would stay in Florence and do a day trip into the Tuscan countryside.
• What time of year are you visiting? If you’re hoping to squeeze in some summer beach time, it makes sense to stay somewhere on the sea like Viareggio or a short drive from the coast like Pisa.
• What’s your budget? Florence is one of the most expensive cities in Italy. So if you’re on a budget, you should try and stay in a smaller town or somewhere more rural. It may be less convenient, but you’re guaranteed better value for money. 

Where to stay in Tuscany Italy

#1 Florence: Best Place To Stay In Tuscany Without A Car.

Location

Florence is the capital of Tuscany and the region’s largest city by far. It’s situated relatively far away from the coast, but it’s ideal as a stop-off as part of a wider Italian itinerary. It’s basically where to stay in Tuscany without a car. There are quite a few tours that leave from here to explore the Tuscan countryside and towns. Plus some amazing wine tasting tours.

Why stay here

Florence is simply gorgeous! The very first time we visited, we instantly fell in love with the beautiful buildings, the incredible collections of art, and the overall elegance of the place. True, it’s always busy, especially during Easter and the summer holidays. But that just means a little more pre-planning to avoid the worst of the crowds.

An ideal place to start a Tuscan itinerary, Florence is a great base for first-time travellers because it’s full of attractions. Priceless works of art like Botticelli’s Birth of Venus and Michelangelo’s Statue of David stuff the packed museums. While the streets overflow with unforgettable architecture like the Cattedrale di Santa Maria del Fiore and Palazzo Vecchio.

The city is undoubtedly a top contender for where to stay in Tuscany for honeymoon couples. It’s filled with elegant restaurants and picturesque places where you can canoodle as the sun sets. We had some lovely evenings here, dining by candlelight and enjoying the golden hour from the Piazzale Michelangelo.

Another of our favourite things about Florence is that even if you don’t have time to get into the countryside to sample local produce first-hand, the city has a couple of amazing markets. Mercato Centrale is a good starting point, but we found that Mercato di Sant’Ambrogio has more of a traditional vibe. You can buy some great Italian souvenirs or gifts from here.

For longer stays, you might opt to stay somewhere less busy and expensive, but for short stays, Florence is very convenient. Plus, if you don’t want to rent a car, you can always just hop on a tour to the countryside for a day to visit vineyards and medieval hilltop towns.

Things to do in Florence

Florence with kids can be a great experience as well.

• Visit the iconic Cathedral of Santa Maria del Fiore.
• Climb Giotto’s Campanile for awesome views over the whole of Florence.
• Walk the 14th-century Ponte Vecchio across the Arno. many of the walking tours of Florence will have this included.
• Explore the immense collection of Renaissance artwork at the Uffizi Gallery on a guided tour. Or the masterworks at Academia Gallery.
• Watch the sunset from the Piazzale Michelangelo.

Pros & Cons of staying in Florence

Pros	Cons
– Tons of stuff to do – Good connections to other cities – No car required	– Expensive accommodation and restaurants – Almost always full of tourists

#2 Siena: Best Place To Stay In Tuscany With A Family.

Location

Siena is about an hour’s drive south of Florence, with both a train and a bus linking the 2 cities together. Containing a population of just under 55,000 people, it’s much smaller than either Florence or Pisa. And it certainly felt less frenetic to us than those two metropolises!

The countryside surrounding Siena is filled with fantastically preserved little towns. We were particularly awestruck by Monteriggioni, whose sturdy walls have survived since the early 1200s. And San Gimignano, which has pillar-like towers that can be seen thrusting upwards into the sky from miles around.

Why stay here

Siena’s combination of city comforts and quieter atmosphere make it perfect for families. There’s still plenty to see, but there’s not quite as much queuing and jostling as in Florence, which works well with younger kids.

Charming and authentic, Siena is home to some incredible buildings that have stood largely intact for hundreds of years. This is why the historic centre has been listed as a UNESCO World Heritage Site. 

Topping the list of things we did here was climb the dizzyingly high Torre del Mangia. It was a tiring 400 steps to the top. But it’s much taller than anything else in the city (and has been since 1348), so the view was truly glorious. Siena Old Town with its top attractions is part of all guided tours.

We were also wowed by the intricate mosaic floors in the city’s fabulous Cathedral. These are only uncovered for a couple of months every year (usually over the summer), so make sure to check the official website if you want to see them. The rest of the time, you’ll just have to settle for sculptures and reliefs by Michelangelo and Donatello – not exactly to be sniffed at!

Siena is also one of the great places to stay in Tuscany for day trips. There are multiple day tours from Sienna to San Gimignano and other parts of Tuscan countryside. We based ourselves here on one of our more recent Italian holidays, and it was very convenient to reach a lot of super cool medieval towns like Volterra as well as Chianti vineyards by car. Just make sure to check up on the parking situation at your hotel before booking.

Even though Siena itself isn’t quite as impressive as Florence, it is much more affordable. That’s worth bearing in mind for larger families as well as travellers on a budget. It’s definitely more wallet-friendly to stay in Siena and visit Florence, for instance, rather than the other way around.

If you only have 3 days in Tuscany, we’d probably skip Siena, just because it’s not quite as breathtaking as Florence. On longer itineraries, though, you mustn’t miss it! For a fulfilling Tuscany road trip, I recommend 7-10 days.

Things to do in Siena

• Enjoy the gothic splendour and artistic masterpieces of Siena Cathedral.
• Explore the Palazzo Pubblico and the Torre del Mangia in the Piazza del Campo.
• Drive north to Castello di Brolio for a wine tour in stunning castle grounds.
• Drive south to the Crete Senesi to see the most famous view of the Tuscan countryside.

Pros & Cons of staying in Siena

Pros	Cons
– Great base for day trips  – Relatively cheap city accommodation – Good for families	– Not as much to see as Florence – No parking inside the city walls

#3 Chianti: Where To Stay In Tuscany For Wine Tasting.

Location

Chianti is where to stay in Tuscany for wine – especially if you’re big on red wine. Sandwiched by Florence and Siena, it’s a good base for exploring both cities, as well as the vineyard-coated hills between them.

People have been fermenting grapes into Chianti wine since at least the 14th century. Today, the vintage is a protected Italian product that must adhere to specific grape and ageing requirements, especially the more prestigious Chianti Classico.

Why stay here

First off, the wine! The region has many vineyards that can be visited, scattered throughout the rolling countryside. One of our favourite was Poggio Amorell, an estate just outside Castellina in Chianti. The winery has a stunning terrace where you can sample various wines accompanied by panoramic views, cured meats, cheese, and bruschetta.

And that’s another reason to stay in Chianti: the food. It’s the perfect wine pairing with delicious delicacies such as finocchiona (a type of salami made with fennel) or even just the local olive oil with freshly made bread. No better place to take a cooking class! Or a wine tasting tour.

Chianti’s location between 2 powerful Italian city-states meant it was the site of many battles between Florence and Siena. The result? It’s filled with fortified villages, many of which have preserved a lot of their original character.

There are quite a few to choose from, but our personal favourite was probably Montefioralle. Essentially just a couple of narrow streets lined by stone houses with tiled roofs, it’s small but perfect. Pop in for a short spell and just soak in the ambience.

There are B&Bs spread throughout Chianti, but we’d recommend heading to Greve for accommodation. It’s a little larger than Castellina and Montefioralle. It also has more artisan shops, wine bars, and restaurants where you can sample the local produce.

Cute old towns, tasty food, and fab wine – these 3 things add up to our perfect romantic getaway. We’d 100% rate Chianti near the top of special places to stay in Tuscany for couples and honeymooners. If you are spending a lot more time in the countryside than Italian cities, make sure you figure what to pack for Italy accordingly.

Things to do in Chianti

• Check out the imposing castle and charming church of Castellina in Chianti.
• Wander the winding streets of Montefioralle.
• Pop into a wine bar in Gaiole, the reputed birthplace of modern Chianti.

Pros & Cons of staying in Chianti

Pros	Cons
– Plentiful wine tasting – Jaw-dropping scenery – Romantic vibes	– A car is essential to get around – Not as many facilities as in Florence or Siena

#4 Val d’Orcia: Best For Charming Towns.

Location

Another place to drink in the amazing Tuscan campagna and top-shelf wine, the Val d’Orcia, lies on the opposite side of Siena from Chianti. The region is basically one big UNESCO World Heritage Site, so expect a lot of fantastic architecture. 

We learned while staying here that despite looking like an all-natural beauty, Val d’Orcia was carefully designed along Renaissance ideals. It’s about an hour’s drive away from Siena, the city-state that masterminded the appearance of the agricultural land and hilltop towns for maximum aesthetic effect. Pretty wild! That was back in the 14th and 15th centuries, but a lot of it has remained unchanged since that time.

Why stay here

Val d’Orcia is quintessential Tuscany, with rolling hills topped by solitary cypress trees and, once in a while, a picturesque hilltop settlement. Some of the most beautiful towns in Tuscany are in this region, including places that are renowned for their wine and cheeses.

One of the most famous is Pienza. This place has a UNESCO citation all of its own because it was completely rebuilt by Pope Pius II to fit his philosophy of an ‘ideal city.’ We can’t tell you whether it was ‘ideal’ to live in Pienza back in the day, but it’s pretty awesome now! Built from beautifully coloured stone that glows in the sun, it features a palace, a cathedral, and many shops selling the local culinary speciality, Pecorino cheese.

Drive about 15-20 minutes east from here, and you’ll come to Montepulciano, on the edge of the Val d’Orcia. Before visiting, we mainly knew the name from its proud wine heritage, and there’s no shortage of enotecas where you can try it, each one occupying a gorgeous historic home.

Both Pienza and Montepulciano are reasons enough on their own to stay in Val d’Orcia, but they’re just two of the many cool towns to explore! Having said that, we wouldn’t necessarily go for accommodation in either of these places. 

For our money, San Quirico d’Orcia is the best option. Although this historic town only has a population of about 2,500 people, it contains quite a few super cute lodgings. From a location standpoint, it couldn’t be better, just off the main road to Siena and smack in the middle of Pienza, Bagno Vignoni, and Montalcino.

Things to do in Val d’Orcia

• Try the wine at Montepulciano while admiring the Renaissance architecture.
• See Pienza and sample the local Pecorino cheese.
• Stop off in the historic centre of Montalcino to try the local vintage.
• Relax in a spa at Bagno Vignoni, a town famous for its thermal baths.

Pros & Cons of staying in Val d’Orcia

Pros	Cons
– Wide open countryside – Beautiful small towns – Delicious wines	– A car is essential to get around – Quite a long drive from Florence

#5 Pisa: Best For Mixing History And Beach Time.

Location

About an hour and a half west of Florence, Pisa is often overlooked as a place to stay in Tuscany. Most people just turn up here for a half day to see the Leaning Tower. While that’s perfectly fair, it misses out on the fact that the city is well-placed for people who want to throw in some beach time during their Tuscan escape.

The city is only about 15 minutes by train and 30 minutes by car to the resort town of Viareggio, as well as having numerous well-serviced beaches within reach.

Why stay here

Where else would we start but with the iconic Leaning Tower?! A favourite for silly holiday photos, it’s quite possibly the most famous building in all of Italy.

Despite the wonky appearance, the campanile was stabilised many years ago by the city authorities, so we were able to climb the tower’s 250+ steps and enjoy the panoramic view from the top.

But Pisa is more than just a single tower with faulty foundations. It’s also a city filled with medieval and Renaissance architecture to be explored on a day tour. Several of the most impressive examples are right next to the Leaning Tower, in the so-called Piazza dei Miracoli (Square of Miracle). 

Begun in the 1000s, the Duomo di Pisa’s fabulous, four-tiered loggia struck us as unique, even after our visits to the many impressive Florentine cathedrals. The Romanesque-gothic baptistery, meanwhile, lays claim to being the largest in Italy and has incredible acoustics –try them out yourself with a sneaky yodel or two!

There’s also a very grand burial monument called Camposanto lining one side of the square, featuring sculptures and frescoes decorating the elaborate architecture.

While the structures in the Piazza dei Miracoli were undeniably awesome, we also found the area super touristy. As an antidote, we headed into the heart of old Pisa, which had a lot more local flavour. True, it does not have the same noteworthy sights as Florence, but the whole atmosphere feels more authentic and lived in.

Overall, we prefer to stay more in the heart of Tuscany rather than in Pisa, which isn’t particularly convenient for visiting Florence or the region’s wine country. Still, it is an option to consider if you want to base yourself somewhere less obvious and/or closer to the beach.

Things to do in Pisa

• Climb to the top of the Leaning Tower of Pisa.
• Test out the acoustics in the Baptistery of St John.
• Explore the palazzi along the Arno River.

Pros & Cons of staying in Pisa

Pros	Cons
– Iconic attractions – Close to the coast	– Fewer famous sights – Poorly located for exploring Tuscany

#6 Viareggio: Where To Stay In Tuscany For Beach.

Location

The Ligurian Sea laps the shores of Viareggio, a city that has been a coastal town since Roman times but was only really put on the map in the 18th and 19th centuries. It was during this period that it started to become a popular seaside spot, first just for the well-to-do and later for the wider public.

From Florence, it’s about an hour and a half by direct train, so you don’t need to rent a car if you plan to just camp out on the beach here. The whole place has good tourist infrastructure, having catered for domestic and international visitors for many decades now. 

Why stay here

Viareggio is one of the best towns to stay in Tuscany, Italy if you’re after a beach resort-style break. The sandy shore stretches for miles, and there are plenty of public and private places to choose from where you can go for sunbathing and swimming. The whole city is full of restaurants, bars, and shops, so there’s no need to worry too much about finding refreshments, regardless of the time of day.

Strolling along the promenade, we passed quite a few art nouveau and art deco buildings from the early 1900s, back when this place was seen as a bit more exclusive and fashionable. These buildings have held up surprisingly well over the past century and lend a bit of substance to what is otherwise a decidedly lightweight city, at least in terms of culture.

Having said that, there is one unmissable stop for culture vultures in the vicinity of Viareggio: the Villa Puccini. A little way out of town but easily reachable using public transport, it’s the former summer home of the great Italian composer Giacomo Puccini. Located in Torre del Lago, it’s now a museum recounting the musical maestro’s life and work. During the summer, the town even throws an opera festival for him.

If you’re coming from somewhere that doesn’t have the luxury of Italy’s sandy shorelines, it’s definitely one of the best places in Tuscany for a well-serviced beach holiday.

Things to do in Viareggio

• Lie on the golden sand and work on your tan.
• Stroll along the seafront promenade, exploring the various cafes and shops.
• Make a pilgrimage to the Villa Puccini at Torre del Lago.

Pros & Cons of staying in Viareggio

Pros	Cons
– Sandy beaches – Loads of convenient amenities	– Tourist-oriented city – Very few places of historical significance

Where To Stay In Tuscany: The Wrap-Up

Honestly, this is one of our favourite parts of Italy, so we have quite entrenched views about where to stay In Tuscany. While Florence is amazing and super convenient, we’ll probably end up choosing Val d’Orcia for our next trip purely because it’s so beautiful – and we love the wine! 

Having said that, all the places we’ve listed here have their pros and cons. As long as you think ahead about the kind of transportation and trip you want, it shouldn’t be too hard to pick the perfect place.

Planning a trip to Italy? Here are some more guides to help you plan your trip –

Italy Itinerary: The classic two-week Italy Itinerary

Italian cities: Rome in 4 days, One day in Florence, 2 days in Venice, Visit the Vatican City, Rome or Florence

Italian regions: Amalfi coast itinerary for 4 days, Lake Towns in Northern Italy, Lake Como in 3 days, Cinque Terre

Souvenirs: Good Souvenirs from Italy

Packing Guide: Packing checklist for Italy

Food in Italy: 21 of the Best Local & Traditional Italian Food you must try

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