Tuscany in One Day
Italy has a charm like no other. Each region is a world of its own—diverse, deeply rooted, and full of beauty.
But Tuscany, with its ancient cities and carefully preserved town centers, feels like the soul of Italy. Nowhere else do medieval streets, Renaissance architecture, and timeless traditions blend together so harmoniously.
This tour was created to celebrate just that. It’s a journey into the heart of real Italy—where you’ll discover the stories, flavors, and faces of a land shaped by centuries of art, rivalry, and elegance.
A day dedicated to the historic centers of Siena and San Gimignano, two jewels of Italian heritage, followed by a drive surrounded by vineyards in the Chianti hills.
Siena and San Gimignano – UNESCO Gems of Medieval Tuscany
Siena is Siena—a city of undeniable character. With its striking red brick buildings, Gothic cathedral, and shell-shaped Piazza del Campo, it’s considered one of the most beautiful historical centers in Italy.
Its UNESCO World Heritage status is a testament to its remarkable urban design, unchanged through the centuries. The old city center is a celebration of human creativity and architectural expression, where every street tells a story.San
Gimignano, perched on a hilltop with a skyline of stone towers, is pure medieval poetry.
Listed as a UNESCO World Heritage Site since 1990, it was the sixth site in Italy and the first in the province of Siena to receive the honor.
Walking through its narrow lanes is like stepping back into the 13th century. Among its highlights are the Torre Grossa, the tallest of the remaining medieval towers, and the Collegiata (Duomo), where you’ll find breathtaking frescoes by Ghirlandaio in the Chapel of Santa Fina.
San Gimignano, Siena & Chianti Full-Day Tour
Departure from Florence – Private or Small Group Tour
Start of the Day – Florence to Siena
Your private English-speaking driver will pick you up at your hotel or villa in Florence (or elsewhere in Tuscany) in a luxury Mercedes vehicle, fully air-conditioned and extremely comfortable.
Your first stop is Siena. Upon request, we can arrange for a licensed guide to take you on a walking tour through the city’s most iconic sights:
- Piazza del Campo, home of the legendary Palio horse race
- The majestic Duomo, one of Italy’s greatest examples of Gothic architecture
- The winding alleys of the Contrade, each rich with history and local pride
Depending on the day, you’ll also enjoy a small tasting of a local delicacy, either in Siena or San Gimignano—a sweet or savory surprise to enhance your Tuscan experience.
Second Stop: Lunch in Siena or in the countryside
Driving in Chianti Countryside and scenic views
For lunch we’ll recommend you a local trattoria in the hear of centro storico di Sirena or vineyard in to a in the heart of the Chianti Classico region, where a traditional Tuscan lunch awaits combined with wine tasting
You’ll be welcomed with:
- A guided cellar visit, where aging barrels tell their own story
- A seasonal lunch with wine pairings, prepared with local ingredients
San Gimignano
After Siena and lunch, you’ll head to San Gimignano, famous for its medieval towers and charming stone streets. You’ll have free time to explore at your leisure:
- Visit the Torre Grossa for a panoramic view of the Tuscan hills
- Step inside the Duomo and admire Ghirlandaio’s Renaissance frescoes
- Browse shops filled with saffron, ceramics, wine, and handmade goods
- Don’t miss a taste of famous gelato, often voted among the best in Italy
Lunch is not included; wine tasting and cellar tour can be customized based on your preferences.
Return to Florence
After, your driver will take you back to Florence. You’ll arrive enriched, relaxed, and deeply connected to the land you’ve just explored.
Giuseppe’s Travel Note
This tour isn’t just a scenic drive through Tuscany—it’s an immersion in the region’s cultural and emotional heart.
Siena, with its proud traditions, breathtaking piazza, and preserved medieval identity, and San Gimignano, with its towers and timeless atmosphere, show two different sides of Tuscany’s greatness.