Lonely Planet Special 2026 / 3 İtineraries To Explore Florence And Tuscany / By Angelo Zinna / Publisher Lonely Planet

With cyprus-lined roads leading to rustic farm stays, awe-inspiring architecture in Florence and a countryside rich in treasures to fill your plate and glass, Tuscany is where travel dreams come true.

These three itineraries cover the highlights and hidden gems of Florence and Tuscany. Ranging in length from 10 to 12 days, these routes will take you all through this beautiful region and can be combined or extended by adding various stops. Whatever you choose, Tuscany is sure to enchant.

1. Tuscany’s incredible art cities: a 10-day itinerary

10-day itinerary
Distance: 300km (186 miles)

Starting and ending in the Tuscan capital, this itinerary will take you through some of the most impressive architecture the region has to offer, with well-deserved food breaks between historic sights. Get your fill of Renaissance art before cutting through picturesque landscapes in search of frame-worthy medieval scenes.

Florence: 3 days

Take some time in Florence to explore dozens of museums, galleries, churches and piazzas filled with Renaissance and contemporary masterpieces. Enjoy the city’s culinary delights and vibrant aperitivo scene before visiting less-crowded historic centers nearby.

Detour: Head up to Fiesole to check out the Etruscan archaeological sites and one of the best views of Florence (30 minutes by bus).

Next stop: Take a train from Santa Maria Novella station to Pistoia (35 minutes).

Pistoia: 1 day

Forget about queues in charming Pistoia, where striped Romanesque architecture adorns the quaint historic city center extending from Piazza del Duomo. Enter the barely lit Cattedrale di San Zeno and the nearby Antico Palazzo dei Vescovi before touring the underground tunnels to learn about the city’s history from a unique perspective. Then jump back on the train to reach nearby Lucca.

Detour: Head to nearby Prato to visit its Palazzo Pretorio or a contemporary exhibition at Centro Pecci (17 minutes by train).

Next stop: Take a train from Pistoai to Lucca (1 hour 20 minutes).

Lucca: 1 day

Enter the enchanting city center of Lucca via the Porta San Pietro and visit the many historic buildings and piazzas. Climb Torre Guinigi for a spectacular view of the city from its forested rooftop, then join the locals for their evening passeggiata (stroll) on the 16th-century walls that surround Lucca.

Next stop: Take a train from Lucca to Pisa (45 minutes).

Pisa: 2 days

Dedicate at least a few hours in Pisa to explore the UNESCO-listed Piazza dei Miracoli. Besides the excessively photographed Leaning Tower, there are fantastic pieces of Romanesque architecture to check out up close. Venture to the Parco Naturale di Migliarino San Rossore Massaciuccoli for a break from the city sights and a chance to spot the wildlife surrounding the estate formerly owned by the Medici.

Detour: Head to Peccioli for a tour of its urban art installations (45 minutes by car).

Next stop: Drive from Pisa to Volterra (40 minutes).

Volterra: 1 day

After a stop in the contemporary art hub of Peccioli continue all the way to Volterra, where Etruscan and Roman ruins surround the medieval core of the ancient city. Learn about alabaster carving in Volterra’s artisanal workshops before continuing onward via the Elsa Valley.

Detour: Make a stop at Andrea Bocelli’s Teatro del Silenzio, an open-air amphitheater built in the heart of the countryside (25 minutes by car).

Next stop: Drive from Volterra to San Miniato (1 hour).

San Miniato: 2 days

Take a couple of days to tour the Elsa Valley, stopping in San Gimignano for a sip of its famed Vernaccia wine, then continue through hamlets like Certaldo Alta and Castelfiorentino before concluding your journey in San Miniato, where you’ll sample mouthwatering white-truffle dishes.

Take your time – from here, Florence is less than an hour away.

2. A road trip through Tuscany: a 12-day itinerary

12-day itinerary
Distance: 300km (186 miles) 

The scenery changes as you drive south from Florence, crossing vineyard-covered hills, cypress-dotted landscapes and Etruscan-era borderland towns. This road trip of a lifetime takes you to world-class wineries, UNESCO World Heritage Sites and farm stays you’ll struggle to leave. Don’t forget your camera and prepare to taste some of the region’s best gastronomic specialties.

Greve in Chianti: 2 days

After a few days in Florence, start exploring the wine lands south of the city, journeying through the Via Chiantigiana, the picturesque road connecting Florence with Siena. Set up base in one of the many agriturismi (farm stays) near Greve in Chianti and go winery-hopping to taste one of the most beloved products in Tuscany.

Detour: On your way to Siena visit the fortified town of Monteriggioni, a historic stop on the Via Francigena (50-minute drive).

Next stop: Drive from Greve in Chianti to Siena (1 hour 20 minutes).

Siena: 2 days

Architectural highlights abound in the elegant city of Siena – take a couple of days to explore the city’s attractions, starting with the sloping Piazza del Campo and its Palazzo Pubblico. Admire the Duomo’s incredible pavement and enjoy the wealth of medieval art exhibited in the museums and cathedrals dotting the historic center of the former city-state.

Next stop: Drive from Siena to Pienza (1 hour).

Pienza & Val d’Orcia: 2 days

As you drive south towards the UNESCO-listed Val d’Orcia through the lunar landscapes of the Crete Senesi area, make a brief stop at the Abbazia di Monte Oliveto Maggiore before continuing to utopian Pienza, the “ideal Renaissance city.” Refuel with a plate of pici (a type of hand-rolled pasta) and some pecorino before further exploration of the picture-perfect landscapes and stone-built hamlets that have made the Val d’Orcia iconic.

Detour: Make a photo stop at the Cappella della Madonna di Vitaleta, between Pienza and San Quirico d’Orcia (15-minute drive).

Next stop: Drive from Pienza to Montalcino (30 minutes).

Montalcino:1 day

As you leave the Val d’Orcia behind, stop in the fortified town of Montalcino, the hilltop settlement home of the famed Brunello di Montalcino wine. Visit the Tempio del Brunello and surrounding enoteche (wine bars) before heading to the countryside for a tasting at one of the area’s historic wineries, such as Ciacci Piccolomini D’Aragona or Fattoria dei Barbi.

Detour: The Abbazia di Sant’Antimo is a worthy stop as you continue further south (15-minute drive).

Next stop: Drive 1½ hours from Montalcino via Abbazia di Sant’Antimo to Pitigliano.

Pitigliano & Città del Tufo: 2 days

This leg is a road trip within a road trip. Tuscany’s deep south is known for its towering hamlets built on tuff-rock formations inhabited since Etruscan times. The Città del Tufo area combines astounding archaeological sites with charming towns connected by twisting roads. Tour Sorano, Sovana and Pitigliano (also known as “little Jerusalem” due to the Jewish population that once lived here) and walk through the Etruscan-era caves and necropolises.

Detour: Recover from the long drive with a dip in the thermal waters of Saturnia (35-minute drive).

Next stop: Drive from Pitigliano to Orbetello (1 hour 20 minutes).

Orbetello: 3 days

Conclude your journey with a restful break on Maremma’s coast, exploring wild beaches and protected wildlife reserves near the town of Orbetello.

If time allows, extend your trip to tour the hidden coves of Monte Argentario and hop on the ferry to reach Isola del Giglio for a well-earned dose of Mediterranean sunshine.