Best Things to do in Tuscany Road Trip in 3 Days

Tuscany, the stunning region in central Italy, is known for its rolling hills, charming medieval towns, rich history, and delicious wines. Whether you’re a first-time visitor or returning for another adventure, a road trip through Tuscany is a perfect way to explore its diverse beauty in just three days. Here’s your guide to making the most of your 72 hours in this captivating region.

Day 1: Florence – The Heart of Tuscany

Start your Tuscany road trip in Florence, the region’s capital and a city brimming with art, culture, and history. Florence is an open-air museum, with iconic landmarks, museums, and picturesque streets.

• Morning: Begin your day at the Piazza del Duomo, home to the Florence Cathedral (Duomo), the Baptistery, and Giotto’s Campanile. Don’t miss climbing to the top of the Duomo for panoramic views of the city.Afterward, explore the Uffizi Gallery, one of the most famous art museums in the world, showcasing works by Leonardo da Vinci, Botticelli, and Michelangelo. Allow a few hours to fully enjoy the masterpieces.
• Lunch: Head to Mercato Centrale for a delicious lunch. Enjoy fresh Tuscan specialties like lampredotto (a traditional sandwich), truffle pasta, or Tuscan steak.
• Afternoon: After lunch, stroll through the Ponte Vecchio, a historic bridge lined with jewelry shops, and head to the Piazza della Signoria, where you can admire the Palazzo Vecchio and replicas of Michelangelo’s David.Finish your day with a visit to Boboli Gardens behind the Pitti Palace. These Renaissance gardens offer stunning views of the city and are a peaceful retreat from the bustling streets.
• Evening: Enjoy dinner at one of Florence’s traditional trattorias, savoring dishes such as ribollita (a hearty soup) or bistecca alla Fiorentina (Florentine steak).

Day 2: Chianti Region – Vineyards and Hilltop Villages

On the second day, take a scenic drive through the Chianti wine region, famous for its vineyards, olive groves, and charming hilltop towns. The winding roads through the Chianti hills offer some of the most beautiful views in Tuscany.

• Morning: Start your drive from Florence and head towards Greve in Chianti, a picturesque town known for its wine and food. Stop at the Greve Wine Museum to learn about the history of Chianti wines.Then, make your way to a local winery for a wine tasting experience. There are many vineyards along the route that offer tours and tastings, such as Castello di Verrazzano or Castello di Ama.
• Lunch: Enjoy a light lunch at one of the local wineries or in the charming village of Radda in Chianti, where you can savor traditional Tuscan dishes paired with local wines.
• Afternoon: Visit Gaiole in Chianti and explore the medieval Castello di Brolio, which has been producing wine since the 12th century. The castle offers tours of its historic cellars and beautiful gardens.Afterward, drive to Castellina in Chianti, another scenic town with narrow streets, old stone buildings, and panoramic views. Don’t forget to visit the Etruscan tombs near the town.
• Evening: For dinner, head to a traditional Tuscan farmhouse and enjoy a home-cooked meal, perhaps featuring wild boar ragu or pappardelle pasta.

Day 3: Siena and San Gimignano – Medieval Charm and Wine

On the final day of your road trip, head south towards Siena and San Gimignano, two of Tuscany’s most well-preserved medieval towns.

• Morning: Start your day in Siena, known for its unique fan-shaped Piazza del Campo and the famous Siena Cathedral. Visit the cathedral’s beautiful interior and take a walk around the Piazza del Campo, which hosts the famous Palio horse race every year.If you’re interested in art, visit the Museo dell’Opera del Duomo, which houses works by Duccio di Guezzoli and other renowned artists.
• Lunch: Enjoy lunch in one of Siena’s traditional restaurants, and try pici pasta, a thick, hand-rolled pasta typical of the region, served with rich sauces like wild boar ragu or tomato and garlic.
• Afternoon: After lunch, drive to San Gimignano, often referred to as the “Medieval Manhattan” because of its towering stone towers. Stroll through the narrow streets and climb one of the towers for panoramic views of the surrounding countryside.While in San Gimignano, don’t miss visiting a local winery for a tasting of the famous Vernaccia di San Gimignano wine, a crisp white wine that pairs perfectly with local cheeses and meats.
• Evening: End your Tuscany road trip with a delicious farewell dinner in San Gimignano, enjoying a traditional Tuscan meal with wine in one of the town’s quaint restaurants.

Bonus Tips for Your Tuscany Road Trip:

• Driving Tips: Tuscany’s roads can be narrow and winding, especially in the countryside. Take your time and enjoy the journey. Ensure your car rental includes GPS, and be mindful of the ZTL (Limited Traffic Zones) in cities.
• Accommodation: Consider staying in agriturismos (farm stays) for an authentic Tuscany experience, where you can enjoy home-cooked meals and a relaxed atmosphere.
• Packing: Bring comfortable shoes for walking, as you’ll be exploring medieval towns and vineyard paths. Don’t forget a camera to capture the stunning landscapes and architecture.

With its mix of cultural landmarks, scenic drives, delicious cuisine, and enchanting hilltop towns, a 3-day road trip through Tuscany is a journey of a lifetime. Whether you’re savoring fine wine in Chianti or soaking in the history of Florence and Siena, Tuscany offers an unforgettable experience that will leave you longing to return.