5-Day Tuscany Itinerary: Florence, Siena, San Gimignano, Chianti & Val d'Orcia

Description
Explore Siena, San Gimignano & Chianti
On the first day of your Tuscany tour, you’ll travel in comfort aboard a GT coach or air-conditioned minibus, guided by expert multilingual escorts. The day begins with a visit to the charming town of San Gimignano, where you'll have free time to explore its medieval streets and famous towers. Next, immerse yourself in the rolling hills of the Chianti region, known for its renowned Chianti Classico wines. Here, you’ll enjoy a wine tasting at a local winery nestled in the heart of the region. Continuing through Tuscany, you'll also have time to explore the historic town of Siena, rich in culture and beauty. The day wraps up with a visit to the picturesque village of Monteriggioni, before returning to Florence to reflect on the unforgettable sights, tastes, and experiences of the day.
Walking Tour of Florence
On day two of your Tuscany tour, dive into the artistic heart of Florence with a captivating walking tour led by an expert guide. This engaging tour allows you to explore the city’s Renaissance landmarks in a fun and unique way, from the iconic Piazza Duomo with the stunning Cathedral of Santa Maria del Fiore, to Piazza della Signoria with the grand Palazzo Vecchio. You’ll stroll across the historic Ponte Vecchio, a bridge that has been a marketplace for local artisans for centuries. The tour also brings you to the Uffizi courtyard and offers a close-up view of the remarkable Brunelleschi Dome and the golden ""Gates of Paradise"" at the Baptistery. With a monolingual guide based on your preferred language and earphones for groups over 15, you’ll uncover 2,000 years of Florentine history and culture. By the end of the day, you’ll feel like a true Florentine, immersed in the city’s art, architecture, and vibrant local life.
A day in the Val d'Orcia
On day three of your Tuscany adventure, embark on the Tuscany Wine & Hills Tour, where you'll explore the breathtaking beauty of the region’s landscapes and savor world-famous wines. Your day begins with a visit to the medieval village of Monteriggioni, where you can enjoy a delightful breakfast (not included) surrounded by ancient walls. Next, venture into the heart of the Chianti wine region, where you'll tour a winery, taste three different wines, and learn about the art of olive oil production. Continue to the picturesque town of Pienza, known for its architectural beauty and stunning views, before heading to Montepulciano, a Renaissance gem famous for its Nobile di Montepulciano wine. After visiting a second winery for a tasting of this esteemed wine paired with traditional snacks, enjoy scenic views on your journey back to Florence, filled with memories of Tuscany’s finest wines and landscapes.
Guided Tour of The Duomo Complex
On day four of your Tuscany tour, immerse yourself in the rich history and stunning architecture of Florence with a guided visit to the Duomo Complex. Accompanied by a licensed guide, you'll explore Florence's iconic Cathedral, Baptistery, and the Opera del Duomo Museum, uncovering the secrets behind these masterpieces. The tour begins with the magnificent Santa Maria del Fiore, known for its awe-inspiring Brunelleschi dome and beautifully intricate marble panels. Your guide will lead you through the complex, sharing fascinating stories about the great artists who shaped its design, including Michelangelo, Giotto, and Donatello. Using HD audio systems, you'll hear every detail as you explore the cathedral's interior, adorned with precious frescoes and sculptures. The journey continues with a visit to the Duomo Museum, home to masterpieces like Michelangelo's Pietà Bandini and Donatello's Mysterious Prophet. This is a must-see experience for anyone wanting to uncover the artistic and architectural gems of Florence.
Chianti Vespa Tour
On day five of your tour, get ready for an unforgettable half-day adventure through the scenic Tuscan hills on an original Vespa scooter. Feel the thrill of riding along quiet, picturesque roads surrounded by the stunning Chianti region’s rolling landscapes and charming medieval villages. Whether you're driving the Vespa or riding as a passenger, you'll have the chance to capture stunning photos of cypress tree-lined avenues and the idyllic Tuscan countryside. The journey also includes a visit to an exclusive winery, where you'll indulge in a wine tasting, savoring the local flavors amidst breathtaking scenery. The tour is complemented by a light lunch, making this a perfect way to immerse yourself in the beauty and traditions of Tuscany.
Included
- Travel by GT coach or air-conditioned minibus
- Expert multilingual escorts
- Wine tastings at three wineries in Chianti and one in Val d'Orcia paired with snacks
- Free time in San Gimignano, Siena, Monteriggioni, Montepulciano, and Pienza
- Monolingual Guided Tour of Florence
- Earphones for groups with over 8 participants
- Chianti & Nobile di Montepulciano wine tasting
- Guided tour of the Cathedral, Duomo Museum, and Baptistery with a licensed guide
- Hire of original Vespa scooter (automatic)
- Helmet, fuel, and taxes included
- Exclusive winery tour
- Light lunch only for the Vespa tour
Excluded
- Overnight stay
- Guided tour of Siena
- Vespa tour not allowed for children (0-12 years old)
- Food and beverages were not mentioned
- Gratuities
- Extras