Siena: Essence of Tuscany Tour 2025

DAY 1 - Arrival

Private or shared transfer from Florence Airport to a charming 3* hotel in Siena

How to explain the city of Siena? Talking about its history? Talking about the famous Palio? Choose the best way for yourself and start dreaming..

Arrival at the hotel and room accommodation.

Free time for dinner, overnight stay in hotel.

DAY 2 - Pienza and Montepulciano Day Tour

Breakfast at hotel.

Meet your guide with a short walk in front of the church of San Domenico in Siena.

Travel south out of town on one of the most panoramic roads of Tuscany, through the characteristic moonscapes of the Crete Senesi. Enjoy brief stops along the way for photo opportunities before visiting a quaint, non touristic medieval hamlet. Continue along this stunning landscape and reach the UNESCO heritage site of the Val d’Orcia, where you come across some of Tuscany’s most iconic postcard pictures.

Arrive to the beautiful, utopian renaissance town of Pienza, one of the first towns to be entirely planned out on paper by important architects of the time. These were called upon by Pope Pius II, the humanist pope who wanted to renovate his native town and bring it new splendor. Spend your leisure time exploring the Romanesque church of Corsignano or the ideal, Renaissance Cathedral and walk along the scenic route overlooking the valleys and hills beyond. Browse the pretty streets of this gem of a town or some of its many shops of local crafts and products.

Visit a local farm for a wholesome and refreshing lunch based mainly on the fresh ingredients produced on the farm. Here you can learn about the pecorino sheep cheese making processes, visit the farm animals and learn about the lifestyle of the area. Weather permitting, lunch will be served on a panoramic terrace, overlooking the valley below.

In the afternoon, visit one of the biggest and proudest of the Tuscan hill towns, Montepulciano. This town was first under the dominance of medieval Siena and then became an ally to renaissance Florence: here you can recognize the influences of both Republics in its architecture and art. Located on a steep hill, you can look over the ledge at the the Tuscany - Umbrian border. Visit the main square, Piazza Grande, and explore one of the many old wineries carved out of the ground below the city, taste the Vino Nobile that is produced by the many important and noble families live here. After a short walk around town with your guide, enjoy some free time in town.

On your journey back to Siena, you can admire the sky light up as the sun sets over the Tuscan hills and vineyards. Don't miss out on this incredible experience in the heart of Tuscany! 

Free time for dinner and overnight stay in hotel.

DAY 3 - Day Off

Breakfast in hotel and free time at disposal.

You will be able to relax and enjoy Siena.

Free time for dinner, overnight stay in hotel.

DAY 4 - Siena: walking through history

Breakfast at hotel and short walk to your meeting point, in front of the church of San Domenico in Siena, where you will meet your professional guide.

Tour begins by taking a look at the magnificent Basilica of San Domenico to admire its architecture and art, as well as the important relic that it contains, of the patron Saint of Italy and Europe: Saint Catherine, who was born in Siena. Then, exploring Siena’s medieval streets and squares and listen as your guide points out the most important historical buildings linked to the city’s main houses of power. Marvel at Rocca Salimbeni, housing the most ancient bank in the world, Monte dei Paschi, home to the main offices and an impressive collection of archives and works of art. Walk to Palazzo Tolomei, which is said to be the oldest private palace in Siena and see the imposing stone tower of Palazzo Chigi Saracini, a mid-12th century palazzo built by the powerful Marescotti family. Currently, this building is the seat of the prestigious Accademia Musicale Chigiana, a music school founded in 1923. Admire one of Italy's most beautiful piazzas, the Piazza del Campo built in the shape of a shell, with the impressive Palazzo Comunale or Town Hall with its imposing bell tower, the Torre del Mangia. This is the square that enjoys one of the most famous medieval tournaments, the Palio horse race, held twice a year by the city's Contrada neighborhoods and is to this day, the heart and soul of this magnificent medieval city. End the tour with a guided visit to one of the most spectacular cathedrals in Italy, the Siena Duomo (Cathedral), with its rich interiors that span the centuries. Your guide will escort you into this breathtaking monument to see impressive masterpieces by Donatello, Bernini and Michelangelo. Admire the exquisite Gothic architecture, the ancient pulpit, and visit the chapels. Walk below the naves and marvel at the Renaissance busts of popes and the intricate marble decorations and stained-glass windows.

Rest of day at your disposal.

Free time for dinner and overnight stay in hotel

DAY 5 - Monteriggioni, San Gimignano and Volterra Day Tour

Breakfast at hotel.

Then little walk to meet your guide in front of the church of San Domenico in Siena, at 9:30 am.

Travel into the Chianti hills and take a walk around Monteriggioni, a medieval fortress with a complete ring of city walls and turrets built in the 13th century and mentioned by Dante in his Divine Comedy: this was once Siena’s main bastion of defense against the armies of Florence. Enjoy its quiet and charming atmosphere browsing the alleys and shops of local crafts and products, or lighting a candle in the local church as the pilgrim's once did.

Continue to the fascinating town of San Gimignano, one of the most characteristic hilltop towns of Tuscany, with its many austere medieval towers that defiantly survived the centuries and are still proudly standing today. Recognized as a UNESCO site of world heritage, this city is a great testimony of medieval architecture. Walk along the ancient route of the Via Francigena, the main route that took all travelers and pilgrims of Europe to Rome and the Holy See. The bustling San Gimignano flourishes with artisanal boutiques of the local trades and stores, selling the towns famous ‘red gold’ or saffron spice as well as the Vernaccia white wine, so traditional and old that Dante mentions it in the 13th century.

After working up an appetite browsing squares, streets, churches and stores, visit a small family-run farm and enjoy a traditional Tuscan lunch prepared using the farm's own seasonal products. During lunch you will taste dishes prepared with saffron accompanied by the refreshing Vernaccia white wine. After lunch travel on on panoramic roads towards Volterra, the ancient Velathri, a city that harmoniously combines Etruscan and Roman ruins with medieval and Renaissance architecture, with the unavoidable modern buildings and furnishings. Visit a small, artisanal workshop and meet the craftsmen that have been working the local alabaster for decades. Witness this ancient art of sculpting this stone into precious masterpieces. Enjoy leisure time walking along the streets of the historical centre, visiting the town’s famous Etruscan museum or simply marveling at the millennia old Etruscan arch, the Roman theatre or the more modern monuments and shops in town.

Frre time for dinner and overnight stay in hotel.

DAY 6 - End of the tour

Breakfast in hotel and private or shared transfer to Florence Airport.

Bye bye Tuscany

PLEASE NOTE: the order of visits may change depending on the day of departure of the tour.