Where to stay on a luxury holiday in Tuscany
So, you’ve decided to treat yourself to a luxury holiday in Tuscany. You’ve got a rough idea of how you’re getting there, and you can already taste the local wine. Now comes the part where you need to choose your home base.
Tuscany is not a one-size-fits-all region. It is a vast, beautiful patchwork of medieval hilltop towns, world-famous historic cities, rugged coastal strips, and quiet, vineyard-draped valleys. Where you stay can set the rhythm of your luxury holiday.
Are you looking to step out of your front door straight into a bustling piazza for a morning espresso, or do you want to wake up to absolute silence, with nothing but rolling hills and olive trees as far as the eye can see?
To help you find your perfect location, we’ve broken down the absolute best destinations in Tuscany for a luxury holiday. Grab a coffee (or a glass of Chianti!), and let’s explore where you should set up camp for your luxury getaway.
Luxury Holidays to Florence
The capital of Tuscany, Florence, is one of the world’s most iconic cities. The historic centre of Florence was declared a UNESCO World Heritage Site in 1982 and attracts millions of tourists each year. Home to the Duomo, Uffizi Gallery, Palazzo Vecchio, Ponte Vecchio, and the Palazzo Pitti, it is a city renowned for culture and Renaissance art and architecture.
Florence is also a city of beautiful gardens; the Iris Garden, Bardini Gardens, Rose Garden and Boboli Gardens all provide an opportunity for peace and tranquillity in this astonishing city during your luxury holiday.
Tips for navigating Florence on a luxury holiday
It is easy to explore the heart of Florence on foot. Its historic centre covers an area of approximately 5 square kilometres, so everything is within easy walking distance. Many of these central streets are also pedestrianised during the day, so going on foot is your only option.
If you need to rest those legs or want to explore a bit further afield, Florence does have a tram network. This connects the city with the airport and with those neighbourhoods outside the historic centre. Contactless payments are accepted on board.
Accommodation and dining recommendations in Florence
If staying overnight in Florence, there are plenty of accommodation options on offer, suitable for all budgets. These include hotels in Florence, B&Bs, as well as Florence apartments.
It’s worth spending at least one night in Florence on your luxury Tuscany holiday, if you can. That way, you can also make the most of the city’s wonderful bars and restaurants.
One of our favourite classic eateries in Florence is Cibreo. The owners have expanded, now offering a formal restaurant, a more informal trattoria, and a café. This is fine dining whilst still retaining a relaxed feel. Or, head to Regina Bistecca to sample Florence’s most famous dish, the Bistecca alla Fiorentina. This is a thick, T-boned steak seasoned with salt and pepper and grilled. Simple but delicious!
Alternatively, sample Florence’s cucina povera and try the Pappa al Pomodoro (a stew made with stale bread, tomatoes and herbs) or Ribollita (a soup made with stale bread, kale, carrots, tomatoes and other vegetables).
Luxury Holidays to Siena
Siena is also famous for its art and architecture. The beautiful Piazza il Campo which is home to 102 metre tall Torre del Mangia is iconic as is Siena’s stunning Duomo. The Duomo’s striking black and white marble façade is as stunning as its interior. Inside, there are incredible frescoes by Pinturicchio as well as works by Pisano, Donatello and Michelangelo. And don’t miss what is beneath your feet. Much of the floor will probably be covered up but there should be sections of the beautiful mosaic open for you to view. More artworks are on display in the Museo Civico in the Palazzo Pubblico, in the Museo dell Opera, in the Complesso Museale Santa Maria della Scala and elsewhere.
However, Siena is also probably most famous for its palio. This horse racing event takes place twice a year, once on 2 July and again on 16 August. Each time, jockeys and horses from ten of the seventeen contrade (wards) of the city of Siena complete to be the first to cross the finishing line. The race is a bareback ride that makes it way around the Piazza del Campo three times. The winner is the first horse to cross the line, even if he does so without his jockey!
Tips for navigating Siena on a luxury holiday
Siena is a very easy city to discover on foot, especially as the historic centre is a Limited Traffic Zone (ZTL). In fact, it will only take 25 minutes to walk from one side of the historic centre to the other. However, if coming by car, this does beg the question on where to park.
The good news is that there are plenty of parking areas. There is free parking at Il Campino and on Via Laterina adjacent to the cemetery. Free parking is also available on the roadside at Strada di Malizia and on Viale Mario Bracci. The latter is a little further out though so you would need to then catch the number 10 or 17 bus into the centre.
There are also paid car parking facilities at the Il Duomo car park on Via del Nuovo Asilo, at Il Campo on Via di Fontanella and at Santa Caterina. Escalators from here will connect you to the historic centre. Or you could opt to park at Siena’s train station or at the Fortress car park, both of which are a bit cheaper.
Car park prices can vary a lot although you will find that all parking is free on public holidays. However, despite the number of car parks, due to the sheer number of visitors to Siena, parking is not always easy, particularly in peak periods. As a result, you may also want to consider coming by bus or train.
The train station is at the bottom of the hill in Siena. However, there is an escalator from the station to Via Vittorio Emanuele II and from here it’s a short walk to the historic centre. Alternatively, you could catch a bus from the station to the historic centre instead.
The bus service managed by Autolinee Toscane has numerous routes to the surrounding neighbourhoods, with buses running every 30 minutes. There is also a Pollicino service which runs every fifteen minutes.
And, if coming to Siena from Florence using public transport, then the bus is actually the quickest option. Tiemme run two different bus services from Florence to Siena – the Rapida (fast bus) and the Ordinaria (slow bus). These take 1 hour and 15 minutes and 1 hour and 30 minutes respectively to reach their destination. And Flixbus also run a bus service between the two cities.
Once in Siena, another option rather than using public transport is to opt for the bike sharing service in the city – Si Pedala. There are bike stations strategically located around the city and over 200 cycle routes to enjoy near this UNESCO World Heritage city. Simply download the Weelo app to use the service.
Accommodation and dining recommendations in Siena
If staying overnight in the city, you can opt to stay in a hotel in Siena, B&B or a Siena apartment. Those staying overnight will need to pay a tourist tax. This varies dependent on the type and standard of accommodation as well as the time of year. Typically, it is between €1.5 and €5 per person per night. We recommend opting for a Tuscany villa in the Siena countryside though.
If you want to sample some typical Sienese cooking, then our favourite restaurant in Siena is the Ristorante Santa Caterina da Bagoga. Also worth a try is Osteria le Logge. We recommend ordering a hearty bowl of pici pasta, followed by one of Siena’s sweet treats. Ricciarelli biscuits are a popular dessert in the city. Or the Panforte di Siena is a rich, honey-based cake most commonly enjoyed at Christmas. If you’re in a hurry, and looking for food on the go, then head to Pizzicheria de Miccoli. It’s a visual feast as much as anything but we think their ricciarelli biscuits are some of the best we have ever tasted!
Luxury Holidays to Pisa
Pisa is synonymous with its Leaning Tower! However, there is so much more to Pisa than just the Leaning Tower. Even in the Piazza dei Miracoli, there is so much more to see, not least the Cathedral and Baptistry. Pisa also has a rich maritime history; it has been a centre for learning for centuries thanks to its university, founded in 1343, and it was the birthplace of scientist Galileo Galilei. Check out our guide to spending 48 hours in Pisa for more information.
Tips for navigating Pisa on a luxury holiday
If arriving at Pisa airport and heading into the city, you can either opt for a taxi or, alternatively, take the PisaMover shuttle. This connects Pisa airport with the Pisa Centrale train station. It runs every day from 6 a.m. until midnight, with departures every 5 to 8 minutes. The journey time is just 5 minutes. Pisa does have a second train station – Pisa San Rossore – which is actually closer to the Leaning Tower, however not all trains stop here.
If hiring a car in Pisa, then you will need to find parking in Pisa outside the ZTL. The free park-and-ride on the Via Pietrasantina is a good option. Alternatively, there are also free car parks on Via Pratale and on Via Paparelli, both within walking distance or a quick bus ride to the historic centre. There is also metered parking along some of Pisa’s streets and paid car parking options such as those on Via Cammeo, Via Vecchia Barbaricina and at the Piazza Vittorio Emanuele.
Once in Pisa on your luxury holiday, you will find that it is a small, easily walkable city. However, if you do get tired, there is a local bus service. Or, another option is to get about on two wheels. Bike rentals are available at Pisa Centrale train station. Or there is a bike sharing scheme with stations throughout the city. However, this isn’t the most user-friendly and arguably not worth the effort if only in Pisa for the day.
Accommodation and dining recommendations in Pisa
Expect to eat well in Pisa. Because of its position near the sea, Pisa is well known for its seafood dishes. Some of the most famous include the delicious spaghetti con le arselle (clams), stuffed mussels, salted cod and anchovies. You should also make a point of trying Cecina (a thin, salted flatbread made with chickpeas) and torta coi bischeri (or pilgrim cake as it is also known, that dates back to the sixteenth century and which is made with pine nuts). If opting for a pizza, ask for the Pizza Pisana which is topped with tomato sauce, capers, anchovies and cheese.
Enjoy an aperitivo in Pisa at either Viavai Café, Arno Vivo or La Gallina Nera. Then head to one of our favourite restaurants in Pisa on your luxury holiday. Fish lovers should head to Branzo or Offish whilst meat lovers should enjoy Cantina Vasari or Capodimonte. Or for local dishes, opt for Osteria dei Cavalieri, La Pergoletta, Il Mercante or Michelin-starred Erbaluigia.
Luxury Holidays to San Gimignano
UNESCO World Heritage Site, San Gimignano, is most famous for its towers. So iconic are they that the town has even been affectionately nicknamed Medieval Manhattan. In reality, only 14 of the original 72 towers are still standing today. And only one of these is open to the public – the 54-metre-high Torre Grossa – which stands in the Piazza del Duomo. It’s definitely worth making the climb to the top of this tower to enjoy the stunning views.
The towers aren’t the only architectural gems to admire in San Gimignano on your luxury holiday. The rest of the town is filled with several more superb examples of Romanesque and Gothic architecture.
Probably the next most important building after the towers would be its cathedral, the Church of Santa Maria Assunta. Step inside to discover the magnificent series of frescoes which line its walls. These depict stories from both the Old and New Testaments. The colours are incredibly bright and vivid, and yet these works have never been restored; these are the original colours as painted in the 1300s.
Tips for navigating San Gimignano on a luxury holiday
San Gimignano is easy to explore on foot. From one side to another, it’s probably only a 15 minute walk. And if you want to enjoy a walk along its perimeter walls, they’re only just over 2 km in length.
For those coming by car, there are a number of car parks immediately outside the walls of the town. These largest (and busiest) of these is P1 Giubileo but there is also P2 Montemaggio, P3 Bagnaia Superiore and P4 Bagnaia Inferiore.
If coming to San Gimignano using public transport, then the nearest train station is in Poggibonsi. From here you will need to take either the number 130 or number 133 bus to san Gimignano. The journey by bus will take approximately 20 minutes.
Accommodation and dining recommendations in San Gimignano
San Gimignano has another famous claim to fame other than its towers and churches. Head to the Piazza della Cisterna and look out for the queues and you will have come across Gelataria Dondoli. The master gelato maker here has twice won the prestigious title of World Gelato Champion and the gelato here is certainly worth the wait!
Another famous export from San Gimignano is its wine. Vernaccia di San Gimignano is a white wine made using the grapes grown on the sandstone hillsides that surround the town. In fact, it’s the only really important white wine in Tuscany, since so much of the region is given over to the production of reds. Dante actually wrote about Vernaccia di San Gimignano wine in the Divine Comedy so you can be reassured that it comes highly recommended!
San Gimignano is also known for its saffron, pecorino cheese and its ham which has also been infused with saffron and dry aged. The production of saffron in this area has a long history. In fact, it was repeatedly used during the wars between Siena and Florence to pay off debts.
This San Gimignano apartment is well-placed to access the public transportation links to the town. Or, for larger groups, this San Gimignano villa will spoil you with views of the town’s towers from the idyllic setting of its private pool. Certainly, given how busy San Gimignano is, particularly in peak season, we recommend staying outside the town itself so that you can escape the crowds.
Luxury Holidays to Montepulciano
Montepulciano’s historic centre is filled with beautiful churches, impressive palaces, picturesque alleyways, and dreamy piazzas. Don’t be surprised if you recognise it as you explore its streets – the town was used to film the popular Twilight vampire series.
Start your visit in the main Piazza Grande, home to the Palazzo Comunale, which bears a striking resemblance to Florence’s Palazzo Vecchio. Visitors can climb the bell tower to enjoy the 360-degree views from the top. These stretch across the Val d’Orcia towards Monte Amiata and Siena as well as across to Lake Trasimeno in neighbouring Umbria.
Alternatively, enjoy the views over the surrounding countryside at the panoramic viewpoints in Vicolo della Mura or Vicolo del Leone, which comes a close second!
The Piazza Grande is also where you will find the Palazzo Nobili-Tarugi, the Cattedrale di Santa Maria Assunta and the Palazzo Contucci. The latter was once the home of Pope Julius III and then the Grand Duke Ferdinand, but is now where you can enjoy a wine tasting and cellar tour thanks to its ownership by a successful aristocratic winemaking family.
Tips for navigating Montepulciano on a luxury holiday
To do Montepulciano justice, you would need to spend 3 or 4 hours here on your luxury holiday. It’s an easily walkable town and the historic centre is pedestrianised. Cars are generally not permitted inside the city walls without a permit.
Driving to the town is relatively straightforward, but visitors do need to be aware of the ZTL (Limited Traffic Zone). There is plenty of parking on the edge of the town, outside the town walls. The parking areas next to the fortress and just outside the Porta al Prato are generally the most convenient.
If you are dependent on public transport, be aware that the train station is about 15 km outside the town, in Chiusi-Chianciano Terme. You will need to catch a bus from here to the historic centre, and these are few and far between. Alternatively, a taxi will cost between 30 and 40 euros.
Accommodation and dining recommendations in Montepulciano
Montepulciano is one of Tuscany’s most picturesque and charming towns. But arguably it is most well-known for it wine! The prized Vino di Montepulciano is a red wine awarded DOCG status that is made using Sangiovese grapes, whilst the Rosso di Montepulciano is a dry red wine also produced in this area. The town itself offers numerous opportunities to sample them all.
And, as you would expect, there are plenty of foods we recommend you sample in Montepulciano to accompany these wines. The hearty reds pair perfectly with the Chianina meat, the pici pasta and the Tuscan bread. Look out for products with the IGP and DOP certifications such as the Cinta Senese ham DOP or the Chianina beef IGP salami and bresaola. And end your meal with a sweet treat such as the almond cantucci dipped in a glass of Vin Santo, or some Tuscan ciambellini. Take a walk along the Via di Gracciano nel Corso if you’re looking to purchase artisanal food and wine to enjoy back in your villa in Tuscany.
Luxury Holidays to Lucca
Lucca is one of our favourite cities in Tuscany. It’s small enough to be able to explore in a day, but if you’re lucky enough to be able to spend longer there, then it’s the perfect base for your luxury holiday in Tuscany.
The city is nestled in the heart of Tuscany, within perfectly preserved walls that have been converted into a scenic 4 kilometre long pedestrian promenade, complete with trees, grassy banks and family-friendly playgrounds. Whether you choose to enjoy the loop on foot or on two wheels by bike, it’s a great introduction to this elegant city.
Inside the walls, Lucca’s wealth of historic churches have earned it the affectionate nickname, ‘the city of a hundred churches.’ Those religious buildings most worth admiring include the Duomo di San Martino, the Romanesque San Michele al Foro and the Basilica of San Frediano.
For the perfect view of Lucca, climb the iconic Torre Guinigi, topped with mature oak trees. Another must-see is the unique Piazza dell’Anfiteatro. This oval-shaped square traces the outline of a former Roman amphitheatre, perfectly preserving Lucca’s ancient past.
Otherwise, just take time to wander through Lucca’s charming cobbled streets, admiring its elegant villas and towers that typically date between the twelfth and sixteenth centuries.
Tips for navigating Lucca on a luxury holiday
Lucca is easily accessible by train with regular connections from both Florence and Pisa. The train station is conveniently located just outside the city walls, within easy walking distance of the historic centre
It is also possible to drive to Lucca. Just take note that the centro storico is a restricted traffic zone (ZTL). Parking outside the walls is recommended. However, once inside, the city is easily explored on foot or by bike.
Residents love to get about on two wheels, and there are a number of bike rental businesses in Lucca where you can hire bikes for your luxury holiday.
Accommodation and dining recommendations in Lucca
Lucca is an absolute haven for foodies. We are pretty confident in saying that there isn’t another Italian city equivalent in size that can boast as many good quality restaurants as Lucca has.
L’Angolo Tondo is our firm favourite. The quality of food here along with the service and the setting in the Piazza dell’Anfiteatro are all faultless. The adjacent Sotto Sotto comes a close second.
Alternatively, for traditional Tuscan fare in a warm, family-friendly setting, Buca di Sant’ Antonio is a top choice, especially in the Summer when outdoor dining is available.
Or for something incredibly innovative, head outside the city walls to Collegio Culinario. The setting of this restaurant may not look much but the food is imaginative and delicious.
Last (but certainly not least) we recommend Osteria da Pasquale. Many would argue that this steals the show with its exceptional food and warm, personal touch from the owner himself.
Luxury Holidays to Arezzo
Arezzo sits nestled in a southeastern corner of Tuscany. Dating back to the Etruscan era and later serving as a key Roman military outpost, it is steeped in history. Often overlooked by tourists, it is perfect if you prefer to discover a quieter, less visited city in Tuscany on your luxury holiday.
The star attraction in Arezzo is the Church of San Francesco, home to Piero della Francesca’s early Renaissance fresco cycle The Legend of the True Cross. However, there are a number of other churches in Arezzo also worth admiring. These include the Romanesque Santa Maria della Pieve, the 13th-century Church of San Domenico and the small but exquisite Church of Santa Maria della Grazie in the lower town.
With its sloped red-brick floor and lined with historical buildings and charming cafes, we think Arezzo’s square is one of the most attractive piazzas in Tuscany, and a must-see on your luxury holiday to Arezzo.
Tips for navigating the city Arezzo on a luxury holiday
Much of the historic centre of Arezzo is pedestrianised. However, if coming by car, visitors will find a number of car parks. We think one of the most convenient is that on Via Pietri. A series of escalators link this car park to the historic centre. However, there are plenty of others to choose from.
If coming by train to Arezzo, it’s important to note that it has 3 train stations – Arezzo, Arezzo Casello 1 and Arezzo Pescaiola. Choose the one simply called Arezzo as this is the closest to the historic centre. It is about a kilometre from here along the Via Guido Monaco to Arezzo’s main piazza. However, there is a bus service if you prefer.
Accommodation and dining recommendations in Arezzo
If staying overnight in Arezzo, there are plenty of accommodation options on offer, suitable for all budgets. These include hotels in Arezzo, B&Bs as well as villa rentals in Arezzo too. Whichever option you choose, you will need to pay a tourist tax. In Arezzo, the tourist tax applies to all accommodation but the amount depends on the type and rating of your hotel or holiday rental. Typically costs are between €1.50 and €3 per person per night, with those under 12 years old exempt from payment.
Luxury holidays to Chianti
If searching for quintessential Tuscan landscapes, opt for a luxury villa holiday in the Chianti region – or Chiantishire as it is affectionately known. Less than 60 minutes from Florence and Siena, its landscape is characterised by rolling hills planted with olive trees and vines, dotted with picture-postcard Medieval villages. Revolving around four main municipalities – Greve in Chianti, Radda in Chianti, Castellina in Chianti and Gaiole in Chianti – a luxury villa holiday in Chianti provides the perfect balance between relaxation and sightseeing.
Luxury holidays to the Tuscan coast
Tuscany may be most famous for its rolling countryside, but a luxury villa holiday on Tuscany’s beautiful coast allows you to discover a completely different side of this beautiful region. With over 300 km of stunning beaches in Tuscany to discover, choose between the wilder, rugged beaches of the south or the pristine beach clubs of the north.
Ready to find your perfect luxury villa in Tuscany?
Whether you see yourself sipping espresso in a bustling Florentine piazza, cycling along the historic walls of Lucca, or watching the sun set over the vineyards from your private infinity pool in Chianti, the perfect luxury villa is waiting for you.
We specialise in matching travellers with their dream Italian escapes. Browse our handpicked, exclusive collection of luxury villas in Tuscany today, and let’s start planning your unforgettable getaway.
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