Tuscany Art Wine Hills Exploration Self-Drive

Welcome to Italy. Upon arrival at Florence airport, collect your hire car from the rental office before driving to your hotel for check-in. Take some time to explore the city’s oldest streets, including a stroll along the Arno River and across the famous Ponte Vecchio. Overnight in Florence.

After breakfast at the hotel, begin your day in Florence with a visit to the Accademia Gallery, home to Michelangelo’s David—an iconic symbol of the city. Take time to appreciate this masterpiece up close and explore other notable works, including Michelangelo’s unfinished sculptures, to gain insight into his artistic process.

Following the gallery visit, enjoy some free time to wander Florence’s charming streets and sample a local lunch at your leisure. In the afternoon, continue exploring the city’s historic centre. Admire Brunelleschi’s Dome and the Baptistery’s renowned golden ‘Gates of Paradise’ in Piazza del Duomo. Stroll through the Uffizi Courtyard and revisit the Ponte Vecchio.

Conclude your day with a visit to the Uffizi Gallery, one of the world’s most celebrated art museums, where you can admire masterpieces by Botticelli, Leonardo da Vinci, Michelangelo, and Raphael. Be sure not to miss Botticelli’s The Birth of Venus and Primavera, among the gallery’s highlights. You will overnight in Florence.

After breakfast at the hotel, we suggest a day trip to Pisa, one of Tuscany’s most visited cities, renowned for its iconic Leaning Tower. Explore the stunning Piazza dei Miracoli, widely regarded as one of the world’s most beautiful monument complexes. Take time to admire the exterior of the Leaning Tower, the Cathedral, and the Monumental Cemetery, each reflecting Pisa’s rich architectural heritage. The Cathedral’s interior is open to visitors—please check availability if you wish to go inside.

As you stroll around this UNESCO World Heritage Site, soak up the atmosphere and capture memorable photos of the Leaning Tower, a symbol recognised worldwide. You’ll also learn about Pisa’s historical significance as a centre of knowledge and culture, home to the prestigious Scuola Normale Superiore, one of Europe’s leading institutions of higher education. Return to Florence for your overnight stay.

After breakfast and check-out, depart for the Chianti region, renowned for producing the prestigious Chianti Classico wine within one of Italy’s top DOCG areas. Driving along the scenic Chiantigiana wine route, you’ll pass rolling hills dotted with vineyards and olive groves. Keep an eye out for the Gallo Nero (black rooster) emblem, a symbol of the Chianti Classico zone, as well as charming hilltop towns, including Greve in Chianti.

Stop in a typical Chianti village where you have some free time to explore its quaint streets and browse local gourmet and souvenir shops. At the end of the day, we continue to your next hotel in Gaiole in Chianti for check-in and overnight stay.

After breakfast at the hotel, you have a full day to explore the Greve in Chianti area at your own pace. This is an opportunity to discover the local villages, vineyards, and countryside independently, allowing you to tailor the day to your interests. You might choose to visit nearby wineries, stroll through charming towns, or simply enjoy the peaceful Tuscan landscape. Overnight accommodation is in Gaiole in Chianti.

After breakfast, set off in your rental car for Siena, a city that flourished as a cultural and artistic hub during the Roman and Renaissance eras. Begin your visit with a walk from Salimbeni Square, home to Monte dei Paschi di Siena, Europe’s oldest bank, then continue to the impressive Siena Cathedral, a prime example of Italian Gothic architecture. Don’t miss Piazza del Campo, renowned for its distinctive shell shape and stunning architecture, as well as its historic Palio horse race held twice yearly.

After exploring Siena, drive approximately 45 minutes to San Gimignano, a medieval hilltop village famous for its 13th-century walls, stone towers, and charming squares. The area is also known for Vernaccia di San Gimignano, a notable white wine. Take time to wander the village and enjoy a gelato from one of its celebrated gelaterias before returning to your hotel in Gaiole in Chianti for the night.

After breakfast at the hotel, enjoy a day at your leisure in Florence. Use this time to revisit favourite spots, explore hidden corners, or simply relax and soak up the city’s atmosphere. In the afternoon, you will return your hire car at Florence airport, concluding your driving journey.