Timeless Tuscany: Cities, Wine & Scenic Wonders in 8 Days
Discover Tuscany at its most captivating, from legendary cities to postcard-perfect countryside, this itinerary blends art, history, wine, and authentic Italian lifestyle into one unforgettable experience.
Begin in Florence, the cradle of the Renaissance, where masterpieces and elegant squares bring history to life. Continue to Pisa to admire the world-famous Leaning Tower.
Travel through the Chianti countryside, with its rolling vineyards and olive groves, and enjoy a wine tasting near the medieval towers of San Gimignano. Explore Siena, a perfectly preserved medieval city centered around the spectacular Piazza del Campo.
Discover Arezzo, an authentic Tuscan gem rich in art and tradition, before ending in the Val d’Orcia, a UNESCO landscape of gentle hills, cypress-lined roads, and timeless villages such as Pienza and San Quirico d’Orcia.
Arrive in Florence, the jewel of the Renaissance, and settle into your 4-star hotel. Surrounded by timeless art, elegant architecture, and vibrant streets, Florence welcomes you with its unmistakable charm. Take the afternoon to relax after your journey or begin your first discovery of the city.
The evening is free to enjoy at leisure, whether indulging in a traditional Tuscan dinner in a local trattoria or simply soaking in the magical atmosphere of the city as it comes alive at sunset.
Start your day in Florence with a delicious breakfast at the hotel before meeting your expert local guide for an unforgettable walking tour through the heart of the Renaissance city. Along the way, discover true masterpieces and iconic landmarks, from Michelangelo’s David to the majestic Palazzo Vecchio and the renowned Uffizi area. Cross the legendary Ponte Vecchio, famous for its historic goldsmith shops, and pause at the playful Fontana del Porcellino, where tradition invites you to make a wish for good luck. After the tour, enjoy free time for lunch and continue exploring the city at your own pace.
Enhance your day with a visit to the monumental complex of Florence’s Cathedral of Santa Maria del Fiore, including the chance to climb Brunelleschi’s Dome. Discover one of the city’s most extraordinary masterpieces as you explore the interior of the Cathedral, admire its magnificent architecture, and stand beneath Vasari’s breathtaking frescoes depicting the Last Judgment.
The visit also includes Santa Croce, one of the most important churches in the city, known for its artistic heritage and historical significance. From the top viewpoints, enjoy spectacular panoramic views over Florence — a perfect highlight to an already unforgettable day.
After breakfast at the hotel, set off for a full-day excursion to discover two of Tuscany’s most charming medieval towns: Pisa and Lucca.
Begin your visit in Pisa, where you will enjoy free time to explore the world-famous Piazza dei Miracoli, a UNESCO World Heritage Site home to extraordinary landmarks such as the Cathedral, the Baptistery, the Monumental Cemetery, and the iconic Leaning Tower.
Continue your discovery through the lively streets of Pisa, including Piazza delle Vettovaglie and the elegant Borgo Stretto, a favorite area for both locals and visitors, perfect for a relaxed stroll among shops and cafés.
Enjoy free time for lunch at your leisure.
Inside the city walls, visit the Cathedral of San Martino, a stunning example of Romanesque style, and continue to Piazza dell’Anfiteatro, built on the remains of an ancient Roman amphitheater and still one of the most distinctive squares in Italy. Discover the archaeological site beneath the Church of Saints Giovanni and Reparata, then stroll through Piazza San Michele, dominated by the elegant Church of San Michele in Foro.
Admire also the Basilica of San Frediano, and take in the city’s skyline marked by the Clock Tower and the famous Guinigi Tower with its iconic rooftop oak trees.
At the end of the day, return to Florence for overnight stay.
After breakfast at the hotel, check-out and journey through the rolling Tuscan countryside towards Siena, with a scenic stop in the enchanting hilltop town of San Gimignano, renowned for its medieval towers and timeless atmosphere—an ideal introduction to the beauty of rural Tuscany.
Continue into the heart of the Chianti Valley, considered the soul of old Tuscany and home to world-famous wines, this region offers an authentic and deeply sensory experience.
Enjoy a guided visit to a local winery, where you will discover the traditions of Tuscan winemaking dating back to the 13th century. Take part in a tasting of fine regional wines and extra virgin olive oils, followed by a typical Tuscan lunch in a relaxed and welcoming setting.
In the afternoon, continue to Siena and check in to your 4-star hotel, with the evening at leisure in one of Italy’s most captivating medieval cities.
Start the day in Siena with breakfast at the hotel before meeting your local guide for a journey through the city’s extraordinary medieval heritage.
Begin your visit at the magnificent Piazza del Campo, the iconic shell-shaped square home to the Torre del Mangia and the imposing Palazzo Pubblico. This historic setting is also where the famous Palio di Siena takes place, the traditional horse race that brings the city’s districts to life in a unique and passionate celebration.
Continue through the elegant streets to Palazzo Tolomei, once the residence of prominent Sienese families, before reaching the breathtaking Cathedral of Siena. Together with its Baptistery, the Duomo reveals an outstanding artistic treasure, including Duccio di Buoninsegna’s Maestà and an early sculpture by Michelangelo depicting St. Paul.
In the afternoon, enjoy free time to further explore the city at your own pace. Overnight stay in Siena.
Arrive in Montepulciano and proceed to a charming villa or agriturismo, surrounded by vineyards and hillscapes, it offers a peaceful atmosphere and panoramic views, perfect for relaxation and an authentic rural experience.
In the afternoon, enjoy free time to discover this stunning Renaissance town, known for its elegant palaces, underground wine cellars carved into the rock, and the world-famous Vino Nobile. Stroll through Piazza Grande, the town’s impressive main square, visit the beautiful Duomo of Santa Maria Assunta, and admire the historic Torre di Pulcinella. From its panoramic viewpoints, enjoy unforgettable views over the Val d’Orcia and the surrounding countryside.
In the afternoon, transfer to Arezzo, where civil and religious architecture blend into a harmonious medieval setting. At its heart lies Piazza Vasari, a striking square built over the ancient Roman Forum and framed by remarkable buildings such as the Palazzo delle Logge by Giorgio Vasari and the Romanesque apse of the Pieve di Santa Maria.
Continue to the Church of San Domenico, home to the powerful wooden Crucifix by Cimabue, before visiting the Church of San Francesco, where you can admire Piero della Francesca’s famous fresco cycle The Legend of the True Cross. The tour also includes the Cathedral of San Donato, dedicated to the city’s patron saint, which overlooks the town from its scenic position.
At the end of the visit, return to your hotel in Montepulciano for overnight stay
After a relaxed morning, check-out and end of tour, as your journey through Tuscany and Central Italy comes to a close, leaving you with lasting memories of art, history, breathtaking landscapes, and authentic Italian experiences.
On request, private transfer to Florence or Rome airport for your departure.
The tour includes:
The tour does not include: