Thinking of planning a road trip to Italy? Then drive around Tuscany, which is a stunning region that serves plenty of opportunities for food and wine-lovers. It is one of the most famous and beautiful regions of Italy, and for a good reason. Whether this is your first visit or you have been to Italy multiple times, the Tuscany region will take your breath away. From ancient cities and good food to cute cafes and vineyards, Tuscany has something to offer everyone. Road tripping in Tuscany is also one of the cheapest ways to travel to Italy, as you can see and do a great deal without putting skid marks on your wallet while enjoying an unforgettable road trip in Tuscany.
You can plan a 4-5 day trip to complete this Tuscany road trip itinerary, considering exploring each location to take in what each area of Tuscany has to offer. You can also book a cheap rental car or a caravan for your road trip. Our extensive Tuscany road trip itinerary will take you through Florence, Arrezzo, Siena, and beyond and offers a glimpse of the unique communities of this renowned region.
Start Your Trip from Florence
Being the capital of Tuscany and the birthplace of the Renaissance, Florence is the perfect place to begin your Tuscany road trip. While traveling around Florence, make sure to check out the famous “David” statue at Galleria dell’Accademia. Purchase online tickets in advance to avoid the queues. Next, head to Boboli Gardens- a beautiful ancient garden overlooking the city.
Also, check out the Duomo, which is the large Basilica in the center of town. Marvel at the art in the Uffizi Gallery, soak in the views from Piazzale Michelangelo, and more. Spend time walking the Florentine bridges such as Ponte Vecchio and relaxing with some gelato as you watch the sunset. The cafes and restaurants in Florence have everything food and wine-lovers could ask for.
Head to the Beautiful Town of Poppi
Just an hour and a half drive outside of Florence, Poppi is a beautiful little gem of a city and your first taste of Tuscan wine culture. Once you arrive, Be sure to stop at Brancaia Winery for a tasting. The charming town of Poppi has a magnificent Medieval castle and is surrounded by the National Park Foreste Casentinesi. It also features a well-preserved 13th-century castle that towers over the entire city. Explore the Castle of Counts Guidi during your time in Poppi. You can also check out Il Capanno, a restaurant that offers fabulous, authentic food with a casual atmosphere.
Explore Arezzo – Wealthiest City in Tuscany
From Poppi, drive south for just 45 min to reach the heart of Arezzo. It is a wonderful stop on your Tuscany road trip because there is so much to see and do. The entire region offers stunning views and is home to so many monuments, cathedrals, and monasteries. Arezzo is the wealthiest city in Tuscany due to its history in gold smithery. Some of the major city attractions include The Town Hall (Palazzo del Comune), Cattedrale di San Donato, and Monumento a Francesco Petrarca that are all worth visiting.
For the best viewpoints, visit the beautiful hilltop Arezzo Cathedral. The Basilica di San Domenico contains the 13th-century “Crucifix” painted by Cimabue, which is a wonderful work of art and a delight to the eyes.
Visit the Historic City Center of Siena
Located just an hour away from Arezzo, Siena is a beautiful stop on your Tuscany road trip itinerary. Explore the historic city center, which is a UNESCO World Heritage Site. The Duomo, also known as the Siena Cathedral, is arguably the most beautiful Duomo in Tuscany and a must-see here. Siena is also known for its Palio di Siena horse race that takes place bi-annually in the oval-shaped Piazza del Campo. For more tourist attractions, check out Palazzo Chigi-Saracini if you love palaces, or visit Saint Catherine Of Siena to know about its history. You can also visit Biblioteca Piccolomini or walk the Piazza del Campo.
Check out Colle Di Val D’elsa and San Gimignano
After your stay in Siena, head to the final destinations of your trip and explore Colle di Val d’Elsa and nearby San Gimignano. Colle Di Val D’Elsa is a beautiful city in the province of Siena. It is a truly medieval hilltop town in Italy and it is very well preserved. In Colle di Val d’Elsa make sure to visit Il Baluardo for a panoramic view of the city, the Palazzo Campana, and dine at the Officina della Cucina Popolare, Arnolfo, or Ristorante Pizzeria il Torrione.
While you are in Colle Di Val D’Elsa, take a short day trip to explore nearby San Gimignano. Just 25 minutes away from Colle Di Val D’Elsa, San Gimignano is one of the most visited towns in all of Florence and is also known as The Town Of Fine Towers. 14 towers remain out of the original 72, which was built in the 12th century, and they are a sight to behold. If you are looking for something a bit different, take a walk in the Riserva Naturale di Castelvecchio, or visit the Museo Della Tortura (Torture Museum), which showcases all sorts of historical facts about medieval torture.