Reset Password

Best Towns to Stay in Tuscany

Your search results
January 3, 2024

Last updated on January 28th, 2024 at 04:56 pm

Tuscany is a central Italian region. It is Italy’s most culturally diverse region and, for many foreigners, one of the best places to visit. The capital, Florence, is dominated by some of the world’s most famous Renaissance art and architecture. Tuscany is surrounded by a rich natural landscape that includes the craggy Apennine Mountains, the beaches of Elba, and the olive groves of Chianti. It has vineyards, well-kept towns with spectacular structures, and a leisurely lifestyle. Tuscany has a population of around 3.73 million people, making it a populated region.

Tuscany’s climatic conditions are varied and pleasant. If you’re in one of the towns along the gorgeous Tuscan coast, you’ll experience a light Mediterranean climate with hot, dry summers and mild winters; but, if you’re in the city’s core, you’ll experience a sub-light Mediterranean climate and a highland climate. The weather is one of the factors that draws thousands of visitors to Tuscany throughout the year. As a result, it’s a good idea to plan ahead of time and bring clothing appropriate for various climates. 

Tuscany is widely known for a wide range of things, many of which are vibrant and exciting. Its art cities, cultural amenities, and outdoor activities are some of the things that it is well-known for. Walking trails, biking routes, swimming activities, and a plethora of superb golf courses can be found all throughout the city, and this provides lots of opportunities to be active and to have fun. There are also art galleries, opera houses, music venues, historic towns, and UNESCO heritage sites to explore. There is no form of boredom, no matter where you stay in Tuscany.

Read Also Where to stay in Florence: our selection of Luxury Private Residences

There are different cities in Tuscany that you can explore where to enjoy your stay and some of which are:


Siena is likely Italy’s loveliest medieval city, and a trip worth making even if you are in Tuscany for just a few days. Siena’s heart is its central piazza known as Il Campo, known worldwide for the famous Palio run here, a horse race run around the piazza two times every summer. Movie audiences worldwide can see Siena and the Palio in the James Bond movie, Quantum of Solace.

Siena is said to have been founded by Senius, son of Remus, one of the two legendary founders of Rome thus Siena’s emblem is the she-wolf who suckled Remus and Romulus – you’ll find many statues throughout the city. The city sits over three hills with its heart the huge piazza del Campo, where the Roman forum used to be. Rebuilt during the rule of the Council of Nine, a quasi-democratic group from 1287 to 1355, the nine sections of the fan-like brick pavement of the piazza represent the council and symbolizes the Madonna’s cloak which shelters Siena.

Palio Dates 2024: Palio di Siena on 2 July 2024. Palio di Siena on 16 August 2024. 

best towns to stay in Tuscany

Where to Stay:

Villa Elsa

Villa Elsa Tuscany Villa near Siena

If you are looking a great location where to hold your family reunion, anniversary party or wedding Tuscan-style, Villa Elsa is the luxury villa you want to stay.

This is the luxury grand villa where Italian and foreign noble families celebrated. Located near Siena in the Chianti region, this luxury estate is now completely restored and features luxurious interiors and spacious areas for the whole family.

Villa Elsa can accommodate up to 32 guests if you rent the guest house. The rates indicated are for renting the villa for up to 26 guests. 



Pistoia is a little-known delight. It lies in the tourist heart of Tuscany, a stone’s throw from Florence, Lucca and Siena, but tends to get missed out by travellers. This isn’t completely surprising. The town is less grand than Florence, less ancient than Siena and less complete than Lucca, and its name doesn’t perhaps sound as pretty. Yet Pistoia is a gem. All the ingredients of an old Tuscan city are there – old walls, striped churches, frescoes, medieval watchtowers, arcaded piazzas – packed into a rather small centre.

Best towns in Tuscany by Haute Retreats

Tuscany Villas for Rent by Haute Retreats


It’s a colorful, vibrant city with soaring buildings, colossal palaces, and brilliant cathedrals. It runs parallel to the original Roman amphitheater’s outline. Lucca is totally contained behind its historic protective walls, which are topped with fantastic parking, allowing you to walk all the way around the city for gorgeous and spectacular sightseeing.

Lucca might be one of the best towns in Tuscany to stay in if you’re travelling with children. It’s small enough, and far less busy than Florence and Siena even in high season. As a plus, the city’s walls provide a green space to ride a bike or walk, and it’s always a pleasure to take a rest from sightseeing. Lucca is a very pleasant and friendly town that despite being discovered more and more by tourists, retains an authentically Tuscan feel.

Villas in Lucca

Best Towns in Tuscany | Haute Retreats


Read Also 5 Tuscany Villas for Rent with Tennis Court


This is also one of the most beautiful cities to visit in Tuscany. The city is brimming with medieval and Renaissance structures, lending it an aristocratic appearance, and the public squares are well designed to serve as event gathering spaces. It’s also recognized for its wonderful weekly market, which is great for buying and selling, as well as churches packed with art by Piero, Della, Francisca and a lively atmosphere that makes this town enjoyable. In addition, Roberto Benigni, a local icon, shot his Academy Award-winning movie Life is Beautiful in Arezzo.

Arezzo Italy Tuscany

Arezzo Italy

Villas in Arezzo and nearby


It’s a hill town with various museums and ancient monuments, as well as lovely, narrow alleyways that evoke a Tuscan ambiance.

Volterra is a charming town situated in the province of Pisa, not far from Florence, Siena and the coast as well. It is well known for its Etruscan origins and for the many remainsbelonging to this era.

Stroll down the historical center, step back in time and enjoy the timeless atmopsphere that surrounds the town: taste its typical products and visit the handicraft workshops, where you’ll find many ideas for souvenirs from Tuscany, especially alabaster hand-made objects, which Volterra is famous worldwide for.

Volterra Tuscany |Haute Retreats

Volterra, Tuscany


Cortona is a delight to explore. With its picturesque winding passageways draped with washing lines and hanging baskets of roses and sage, it will leave you with an eager sense. Markets are places you would enjoy visiting, especially on weekends. There are lots of beautiful scenes for your view. And also, there is the Garibaldi square and the Santa Maria cathedral in a medley of red wines and lampredotto sandwiches.

Montepulciano, Tuscany

RELATED Tuscany Villas: Most Beautiful Interiors


This village is known for its eponymous, full-bodied red grape variety. Many people come to see this town because of its natural beauty. Close-knit alleyways wind their way up to the city’s heart, where the piazza grande gleams with marble and travertine wonders. There are also slanting tiled roofs that flow down into the pine like a river.


Read More The most beautiful Italian Villas Where to Stay


Another exciting place in Tuscany is Suvereto. Its located between the forests of Livorno province, which extend westward into the steep hills of Campiglia Marittima, and the grasslands and marsiliana reserve, which extend eastward. Travertine and rough-hewn stone buildings dominate the town’s center. Matteotti, a boulevard lined with slow-food gourmet restaurants and cell phone shops, is located in the heart of the city.

Barga Tuscany

Barga Tuscany


Barga is the most important hilltop town in Garfagnana, the area set in northwestern Tuscany in the province of Lucca, famous for its marvelous and varied landscape that offers hundreds of outdoor activities, exploring the territory and its surroundings.

If you intend to go to Garfagnana, Barga is one of those stops you absolutely cannot miss visiting! It has gained prestigious awards for the quality of its tourist services, like the Italian Touring Club Orange Flag and the Città Slow award. It has also been officially included in the list of One of the Most Beautiful Villages in Italy for its historical and artistic importance.

Florence, Tuscany

Florence, Tuscany, Haute Retreats


Florence, the capital of Tuscany, is a large city worth visiting or taking a tour of. The Uffizi Gallery is just one of the many attractions in this lovely city. The breadth and extent of this gallery’s collection is mind-blowing. It has works of notable 14th-century artists, as well as works that show the progression of styles and subjects.  If you are an art lover, this is the best place to visit or stay.

Villas and Private Residences in Florence and nearby, click here


San Gimignano, Tuscany, Haute Retreats

San Gimignano, Tuscany


San Gimignano

If you want to know or see what Tuscany was like in the Middle Ages, go to San Gimignano, a nearly untouched ancient village. It was once the principal pilgrim and commercial route to Rome, but as the route deteriorated in the late Middle Ages, new structures and constructions ceased, and the hilltop town was left to itself. In the city, you will discover some works by Domenico Ghirlandaio, Benozzo Gozzoli, and Benedetto da Mariano but most of the interiors have been decorated and reconstructed by artists. 


Visit our selection of  Tuscany Villas for Rent 

Tuscany Luxury Villas for rent | Haute Retreats

our Italian Villas for rent Italy Villas & Luxury Resorts | Haute Retreats

More importantly, you will love meandering down its small winding lanes and admiring the towers while admiring the completely intact 13th-century fortifications.  These are the beautiful cities to visit and explore in Tuscany, and I am certain that you will love them when you visit.

Contact us and let us create an itinerary and arrange experiences during your stay in Tuscany. 🙂


Have you ever been in Tuscany?

Which town did you like the most?

Tuscany Villas for Rent by Haute Retreats

Contact Haute Retreats to plan a trip, our team of expert travel designers can recommend the best villas, luxury resorts, restaurants and activities for your interests.

  • Advanced Search

    Ages 13 or above
    Ages 2 to 12
    Under 2 years
  • booking form Haute Retreats
  • Contact us:


  • WhatsApp 24/7 + 39 333 206 5514

  • Toll Free From USA and Canada

  • + 1 888-279-6444

  • elite club program by Haute Retreats
  • Follow Us

  • trust pilot