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Hey, pirates! Are you a real Italy fan and want to explore the country on your own? How about touring in a rental car through Tuscany? This beautiful region of Italy is one of the most popular vacation destinations in the country and has a lot to offer in terms of scenery, cuisine and culture. Tuscany offers ideal conditions for a relaxing and restful vacation.
The city is synonymous with cultural and art cities, rolling hills, wine-growing and a coastline with wide sandy beaches and great nightlife. To bring you closer to the treasures of Tuscany, we have put together a short Tuscany tour itinerary. Of course, you can change the route as you wish. Our trip is merely intended to serve as inspiration.
If you decide to go on a road trip through Tuscany, you’ll need to determine whether to organize the trip yourself or join a guided tour. Guided tours cover all the well-known sights of the region. You can rely on experienced tour guides and have support in case of emergencies. Those who choose to travel independently won’t have a direct contact person in case of issues and may have to deal with language barriers. However, self-guided road trips offer the advantage of designing your route according to your own preferences. You only travel as far as you want each day. And if you find a town you particularly like, you can simply stay there a little longer. This level of spontaneity and flexibility is often lost when traveling with a larger group.
The amount of time you’ll need for your vacation in Italy depends on how much time you want to spend at each stop along the way. In general, a road trip through Tuscany can be comfortably completed in one week. The region is roughly the size of New Jersey. If you want to include a few relaxing beach days on the Mediterranean coast as part of your road trip, you should plan for a vacation lasting about ten to fourteen days.
Shopping: Most of the shopping facilities are located in Corso Italia and Borgo Stretto.
Breakfast: At Lilli (Via Aurelia Nord 15), get a large selection of cornetti (pastries) and other sweet baked goods, which are all homemade. Breakfast is available until 11 am, while Monday is a rest day. Lilli is also the right choice for an aperitivo. Alternatively, you can go to Enrico diagonally across the street.
Eating pizza: La Cereria is very popular with the locals, so you should definitely make a reservation. Treat yourself to a delicious stone-oven pizza and a tasty red wine. However, Tuesday is a rest day.
Eating fish: The best fish restaurant is La Nuova Rampa (Viale Gabriele d’Annunzio 74). Try Mare Caldo and afterward Pasta Pescatore, Pasta Astice, or Pasta Scampi. The portions are very large. You can easily share a portion. Monday is a rest day. It is recommended to make a reservation.
Snacks in a beautiful atmosphere: At Caffetteria Dantesca, you can sit outside in good weather and enjoy an affordable meal. The staff are very friendly, and there is great live music.
Leaning Tower at night: No crowds of people and simply peace and quiet.
It’s a lot of fun to drive along the winding roads or railways in Tuscany and watch the uniquely beautiful landscape fly by. However, there are a few highlights you definitely shouldn’t miss. For a ten-day road trip, a route from Pisa into the hinterland and back to the coast is a good option. You start in the city with the legendary Leaning Tower and drive from there to Lucca.
This elegant city on the Serchio River is especially known for its well-preserved historic old town. Here, you can also marvel at the Renaissance-era city wall. Take a walk along the town's distinctive fortress walls or make a detour to the Puccini Museum. From Lucca, the journey continues to Florence. Plan at least two days to explore this exciting city.
The Cathedral of Florence (Cattedrale di Santa Maria del Fiore)
The stone bridge Ponte Vecchio
Palazzo Vecchio
In the evening, immerse yourself in the nightlife of the city. Popular clubs in Florence include:
Universale Club
Tenax
Rio Grande
You leave Florence to visit the nearby Chianti region. A wine tasting in Gaiole in Chianti is, of course, a must. The next stop is Siena, the city with the famous Piazza del Campo. The Palio di Siena, a famous horse race, is held here twice a year. From Siena, you will soon reach the romantic San Gimignano, which is situated between the picturesque valleys of the Val d'Elsa.
The town's architecture has been declared a UNESCO World Heritage Site. Volterra is one of the most beautiful towns in the region. The Porta all'Arco from the old city wall dates back to the 4th century BC and has been preserved to this day.
At the end of this Tuscany tour, head for the Etruscan Riviera, stroll through the town of Cecina or relax by the Mediterranean Sea.
One of the hidden gems in northern Italy is the district of Figline Valdarno. The Palazzo Pretorio, the town hall palace, features a clock tower from the 13th century. Inside the building, you can admire the intricate terracotta statue, Madonna col Bambino tra i Santi Sebastiano e Antonio Abate (Madonna with Child between Saints Sebastian and Anthony the Abbot).
On a solo trip to Florence? Or does your Florence vacation package include a group getaway? Discover the best areas to stay in Florence below.
In addition to the well-known major cities, there are smaller towns that are particularly appealing to Tuscany travelers. One such place is Montecatini Terme, located halfway between Pisa and Florence. This town is not only known as a spa resort but also as a hub of Art Nouveau architecture.
Our Pirate tip: In the northern part of town, visit the impressive dripstone cave Grotta Maona during the summer months.
If you are planning your tour of Tuscany for the summer, put Monteriggioni di Torri si Corona on your list. At this medieval festival in Monteriggioni, which takes place over two weekends, you can experience knights' games and colorful costumes. You'll also get to try some delicious treats. Great fun - not just for fantasy fans.
Culture is, of course, a big part of Tuscany, but it’s not everything. Make sure to add (at least) one relaxing beach day to your Tuscany tour itinerary. The diverse coastal landscape offers something for every beach lover.
In the northern part of Tuscany, you’ll find the Riviera della Versilia with its fine sandy beach. It stretches for about 18 miles and is especially well-suited for families with children, as the sand slopes gently into the water. You can relax on a sun lounger against the stunning backdrop of the Apuan Alps while the kids play in the shallow water. Not only do the mountains create a picturesque view, but they also shield the area from chilly northern winds, providing you with perfect beach weather.
The southern coast of the region captivates visitors with its untouched natural beauty. A true classic is the Parco Regionale della Maremma, a protected nature reserve. The beaches of southern Tuscany are a hotspot for water sports enthusiasts, who enjoy ideal conditions there. Punta Ala is a well-known destination among sailing enthusiasts from far and wide.
Our Pirate tip: If you want to go swimming in southern Tuscany, head to Castiglione della Pescaia. This dreamy little fishing village features small coves and a romantic sandy beach, perfect for a tranquil seaside experience.
A little further south lies the Costa degli Etruschi (Etruscan Coast), a region known for its diverse vegetation. Here, you'll find a mix of golden sandy beaches and dramatic cliff formations along the steep coastline. Some of the most beautiful beaches on the Etruscan Coast can be found here, offering a stunning mix of natural beauty and relaxation.
San Vincenzo
Piombino
Marina di Castagneto
Alternatively, you can take a ferry trip and spend your beach day on the Island of Elba. Here, you’ll find one of the most beautiful swimming spots in all of Tuscany – Fetovaia Bay. The sea is crystal clear, and the trees reach almost to the water's edge. You can spend your leisure time on a natural white beach made of fine granite sand. This spot is especially appealing to vacationers seeking peace and tranquility. Not far from the beach, there is a surf school. If you’re a beginner wanting to try your first wave on a surfboard, this is the place to be. Advanced surfers also take on the waves in Fetovaia Bay, making it a great destination for surfers of all skill levels.
There are various transportation options for exploring Tuscany. Which one you choose depends on the time you have available and the level of comfort you want during the tour.
Traveling by train is a stress-free and environmentally friendly way to explore Tuscany. The railway connects all the major cities in the region. The well-developed network of Ferrovie dello Stato (the national railway) features several branches extending from the main line to Rome.
For summer travel, it’s advisable to reserve seats in advance to ensure a comfortable journey. Florence serves as the central hub of the region. From here, train lines run via Prato, Pistoia and Lucca to Viareggio, via Empoli, as well as Pisa to Siena and via Arezzo, Cortona and Chiusi towards the capital.
Our Pirate tip: One particularly scenic route is the line from Lucca to Aulla. Along the way, you’ll pass the picturesque Castelvecchio di Garfagnana and travel through a romantic landscape. It’s a breathtaking journey for those looking to experience Tuscany’s charm in a unique way.
After arriving in Pisa, you’ll pick up your rental car and head to the city. Check into your hotel and start your exploration. Pisa is world-famous for its Leaning Tower. On the Piazza dei Miracoli (Square of Miracles), you can visit the Cathedral, the Tower, the Baptistery, and the Camposanto cemetery.
Another masterpiece of Italian architecture is the Santa Maria Assunta Cathedral. Inside the Battistero, you can admire the hexagonal pulpit by Nicola Pisano. A unique highlight is the cemetery in the form of a monumental cloister.
Next, head to Florence. Leave your car behind and take the train from Montecatini to Florence and back (about a one-hour journey). Tickets cost around $3-4 per person per trip. It’s best to purchase round-trip tickets in advance to avoid long queues at Florence's train station. You can check departure times on the Trenitalia website.
Important: Be sure to validate your train ticket at the station!
Florence is considered one of the world’s most important centers of art. It is home to one-third of all Italian art treasures. Visit Santa Croce, the largest Franciscan church in Italy, which serves as the burial site for some of Italy's most famous figures in literature, art and history. Another highlight is Palazzo Vecchio on Piazza della Signoria, with a replica of Michelangelo’s David.
Other highlights here include the baptistery of San Giovanni, dedicated to Florence's patron saint, and the Palazzo Medici-Ricardi. We also recommend a visit to the Uffizi Gallery, the world-famous art gallery with works of European paintings. Afterward, you can take a leisurely stroll through the alleyways of the city downtown and end the day with a coffee shop in the Piazza della Repubblica before taking the train back to your hotel in Tuscany.
The journey continues to Lucca. With its beautiful medieval city walls, Lucca is also known as the City of a Hundred Churches. You can only enter the historic center, which is roughly a square mile in size, through one of the seven gates of the city wall. On your tour of Lucca, you can visit the market square. It owes its impressive round shape to its origins as a Roman amphitheater. Piazza San Michele, with the church of San Michele in Foro and the Palazzo Pretorio, is also well worth a visit.
And then it's on to the UNESCO World Heritage Site of Cinque Terre. Here, you have various options for exploring the surrounding area. You can discover the most beautiful places on foot or by boat, car and train (tickets are available directly on-site). In a car, you can reach the stunningly beautiful stretch of coast in around 1 1/2 to 2 hours.
Even today, it is still a wonderful little world of its own, which has managed to maintain its unspoiled nature with great tenacity, aided by its rough and untamed nature. Visit Monterosso, the western village of the Cinque Terre or Vernazza. It is perhaps the most beautiful village of the Cinque Terre, with its romantic harbor and old tower.
Afterward, you can visit the beautiful city of Siena, which is a work of Gothic art. It seems as if the clock stopped centuries ago. A winding old town with narrow streets lined with tall palaces made of rust-brown brick helps to reinforce this impression. The historic center is grouped around the Palazzo Pubblico, with its Torre del Mangia on the three ridges of the hill in the shape of a three-star. From here, you have a wonderful view of the famous Piazza del Campo.
Then, you should head to San Gimignano. Let yourself be enchanted by one of the most magnificent landscapes of hills, fields, countless vines and olive groves. You can recognize San Gimignano from afar by its towering towers. The Basilica of Santa Maria Assunta, the Palazzo del Popolo with the Museum Civico, and the Piazza della Cisterna, with its pretty fountain, are well worth a visit.
Your last tour takes you to the characteristic cityscape of Pistoia, which has its origins in the Middle Ages and the Renaissance. It shows how art can become a way of life. Stroll through the narrow streets, past ornately decorated buildings. Then, continue to the medieval village of Vinci, the birthplace of Leonardo da Vinci.
You can use the morning to buy some souvenirs. Please allow enough time for the journey to the airport and the return of the rental car.
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