Tuscany is home to some of Italy’s most distinctive cities, each with its own history, atmosphere and rhythm. From Florence and Siena to Lucca, Pisa, Arezzo and San Gimignano, discover six places to include in your Tuscany itinerary, with ideas for what to see, what to experience and how to combine cultural visits with the surrounding countryside and local food traditions while staying in a luxury villa in Italy.
Florence is Tuscany’s cultural capital and a natural starting point for discovering the region. In its centro storico, the Cathedral of Santa Maria del Fiore and its terracotta dome dominate the skyline, while the Uffizi Gallery brings together works by some of the leading artists of the Renaissance. From there, a walk towards the Arno River leads to the Ponte Vecchio and its long-established goldsmiths’ workshops.
Beyond its museums and Renaissance architecture, Florence offers plenty to experience as a family. The Boboli Gardens provide space to explore outdoors, while the climb to Piazzale Michelangelo rewards visitors with splendid views over Florence and the surrounding hills. Food is equally important to the city: markets, traditional trattorias and cooking classes offer different ways to discover Florentine cuisine, from ribollita and pappa al pomodoro to bistecca alla fiorentina.
Among our villas in Florence, Villa Verena and Villa Viti offer two places from which to explore the city and its surroundings.
Siena has retained a distinctly medieval character. At its centre, Piazza del Campo forms the heart of the city and provides the setting for the Palio, the historic horse race held twice each summer. Nearby, Siena Cathedral stands out for its striped marble exterior and richly decorated interior, while the surrounding streets and historic buildings form part of a centro storico recognised as a UNESCO World Heritage Site.
The city also has a strong culinary identity. Local specialities include pici, thick hand-rolled pasta traditionally served with simple Tuscan sauces, as well as panforte and ricciarelli. Beyond the city walls, vineyards and rolling hills make Siena an ideal gateway to the surrounding countryside and an easy addition to a wider Tuscany itinerary.
Villa Assunta and Casale Delle Stelle make it possible to combine visits to Siena with time spent exploring this more rural side of Tuscany.
Lucca stands apart for its remarkably well-preserved city walls. Today, the broad, traffic-free ramparts form a tree-lined circuit around the historic centre, making cycling or walking along them an ideal way to explore Lucca. Along the route, views open over gardens, church towers and the rooftops below.
Inside the walls, Piazza dell’Anfiteatro follows the oval footprint of the ancient Roman amphitheatre that once occupied the site. From here, narrow streets lead towards churches including San Michele in Foro and San Frediano, passing cafés, local shops and beautiful old buildings along the way.
The compact scale of the centre makes Lucca particularly easy to explore with children, while its quieter streets offer a contrast to the popularity of Tuscany’s larger art cities. Villa Marco and Casa Felice offer two options for staying in the area.
Pisa is inevitably associated with the Leaning Tower, one of Italy’s most famous landmarks, but the city rewards visitors who venture beyond its best-known monument. Piazza dei Miracoli brings together the tower, cathedral, baptistery and Camposanto in one remarkable ensemble of historic buildings and remains the obvious starting point for a first visit.
Beyond the square, the atmosphere changes. Walks along the Arno River pass colourful façades and historic palazzi, while Piazza dei Cavalieri introduces another chapter of the city’s architectural heritage. Exploring these quieter streets reveals a more understated side of Pisa, shaped by its university and everyday Tuscan life as much as by its iconic landmarks.
Pisa is also well placed for exploring western Tuscany and can easily form part of a broader Tuscany itinerary. Villa Rivela and Villa Sybille offer two options for staying in the surrounding area.
Arezzo offers something special for travellers interested in art and local life. Its artistic heritage is particularly visible in the Basilica of San Francesco, home to Piero della Francesca’s celebrated fresco cycle The Legend of the True Cross. Piazza Grande, surrounded by medieval and Renaissance buildings, forms the architectural heart of the town.
Arezzo is also renowned for its antiques tradition, with a large market held each month in and around Piazza Grande. Away from the crowds of Florence and Siena, the city can feel like a hidden gem for visitors exploring eastern Tuscany, while still offering a rich concentration of art and architecture.
The surrounding countryside adds another dimension, with vineyards, olive groves and traditional restaurants providing an introduction to regional food and wine.
Villa Maestani and Villa Rosadi offer two places to stay in the surrounding countryside.
San Gimignano is instantly recognisable by the medieval towers rising above its rooftops. Fourteen survive today, reminders of the rival families who once used them as expressions of wealth and influence. Together with the historic centre, they give the town one of the most recognisable skylines in Tuscany.
The centre is compact enough to explore on foot as a family, from Piazza della Cisterna to streets opening onto splendid views of vineyards and cypress trees. Its popularity means the main squares can be busy during the day, but quieter streets still reveal a more intimate side of the town.
San Gimignano is also closely associated with Vernaccia di San Gimignano, the local white wine produced in the surrounding countryside.
Villa Querano and Villa Astrale offer two options for staying in this part of Tuscany.
Villanovo’s collection extends across Florence, Siena, Lucca, Pisa, Arezzo, San Gimignano and Pistoia, as well as the countryside of Chianti and Val d’Orcia. Travellers can choose between staying within reach of Tuscany’s art cities or settling among vineyards, olive groves and cypress-lined hills.
Depending on the property, our villas in Tuscany feature a private swimming pool, landscaped gardens, house staff, private chefs and tennis courts. Larger properties provide additional space and privacy for holidays shared with family or friends.
Our dedicated concierge accompanies guests before arrival and throughout their stay, helping with practical arrangements as well as experiences suited to the region. Depending on the property and availability, this can include airport transfers, private chefs, food and wine experiences, cooking classes or activities for families.
