This is the Perfect Tuscan Road Trip
Planning the ideal Tuscan road trip itinerary isn’t simple, but it’s well worth the effort. In fact, with cute little towns and bigger cities home to hidden gems, staying a few days is sometimes not enough.
I’ve prepared the perfect Tuscan road trip, which you should follow whether you stay in the region for a week, a month, or all year round, even during the Italian winter in December.
If you’re a digital nomad working remotely or simply on holiday in Italy, this road trip also applies to you.
This Tuscany itinerary is perfect for anyone dreaming of delectable Italian cuisine, spectacular sunsets, and Tuscan wines. Italy is simply one of the best places to visit in Europe, and you can’t leave without going on a Tuscan road trip.
After spending many months traveling throughout Italy over a number of years, I’ve put together this comprehensive guide to visiting the country.
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Table of Contents
- This is the Perfect Tuscan Road Trip
This is the Perfect Tuscan Road Trip
Explore Florence
There’s no better location to begin your road trip than in Florence, the capital of Tuscany, the Cradle of the Renaissance, and one of the world’s most popular travel destinations.
I recommend at least two full days in Florence to see all the major attractions and explore the most delicious local delicacies.
Admire the art in the Uffizi Gallery, enjoy the views from Piazzale Michelangelo, and shop for gold on the Ponte Vecchio.
After that, head to Mercato Centrale and get astonished by the Duomo. Of course, don’t forget to see Michelangelo’s David at the Galleria dell’Accademia.
However, if you want to create an itinerary for a Tuscany road trip, here are some important driving instructions: don’t pick up your rental car until the day before you depart from Florence.
The great thing is that you don’t necessarily need to rent a car in the city. You’ll be able to book many unique day trips from Florence that are worth the trip alone.
Limit your expenses by abandoning your vehicle until you’re ready to go into the countryside.
What to Do in Florence
- Uffizi Gallery – book your priority guided tour here!
- Ponte Vecchio
- Palazzo Vecchio
- David of Michelangelo
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Croce in Florence
Where to Stay in Florence
Hotel Santa Maria Novella
This 4-star hotel is nestled in Santa Maria Novella, one of the most central locations. It has multiple rooms that comfortably accommodate couples or families with children. All bedrooms have a private bathroom with modern amenities and free Wi-Fi. See availability and prices here!
Hotel Lungarno – Lungarno Collection
Lungarno Hotel is the ideal accommodation for travelers searching for comfort and luxury in a win-win location. Professional business services are available on-site, too. The rooms are bright, welcoming, clean, and spacious.
There’s a bar and restaurant downstairs. It is conveniently located near the train station and all major attractions, such as Ponte Vecchio and Palazzo Pitti.
See availability and prices here!
Plaza Hotel Lucchesi
If you’re interested in staying in an upscale hotel with a stunning view of Florence, Plaza Hotel Lucchesi is what you’re looking for. You can enjoy the premium location near the Arno River and Piazza della Signoria. Apart from that, the swimming pool on their rooftop is simply a feature you don’t want to miss out on.
See availability and prices here!
Drive to Lucca
The beautiful, laid-back Lucca is the ideal first stop on your journey around Tuscany. It’s also an excellent location to get used to driving and parking in Tuscan cities.
It’s not too big, not too little, full of great properties, and historical attractions. Moreover, finding a parking space outside the city walls isn’t difficult.
Take a break from all the sights and head to the Walls of Lucca and admire the Guinigi Tower. Also, don’t miss the San Frediano Basilica and indulge in some local delicacies you’ll love.
The typical dishes from Lucca are Veal Dish (Rovelline Lucchesi), Porridge (Matuffi), and the famous Egg Dish, Frittata di Vitalba.
Extra tip: I always use Discover Cars for renting cars on my vacations. It is a great aggregator that will help save up to 70% on your car rental. Get your deal here!
What to do in Lucca
- Guinigi Tower
- Walls of Lucca
- St Martin Cathedral
- Plaza del Anfiteatro
- San Frediano Basilica
- Chiesa di San Michele in Foro
If you find it easier, you can always go on a walking tour —it takes 2 hours, and you will see the most important attractions, background, and information.
Where to Stay in Lucca
Best Western Grand Hotel Guinigi
Grand Hotel Guinigi is a stunning 4-star hotel located right outside the Walls of Lucca. In addition to its great location and affordable rates, they have great amenities such as a sauna, meetings, game rooms for the kids, and even a charger for electric cars.
This is certainly one of the best options if you’re planning to spend a few days in Lucca.
See availability and prices here!
Hotel Alla Corte degli Angeli
Alla Corte degli Angeli is a lovely, old-world hotel that is located just within the city walls of Lucca and close to the cathedral. The amenities at Hotel Alla Corte degli Angeli include free Wi-Fi and well-appointed rooms with elegantly decorated walls. Frescoes on the walls add to the ambiance.
See availability and prices here!
Hotel Palazzo Alexander
Hotel Palazzo Alexander is nestled in the center of Lucca, very near Porta San Donato. Rooms are equipped with free Wi-Fi and air conditioning, should you plan a Tuscan road trip during the summertime. Most rooms here have traditional wooden floors and marble bathrooms.
The Palazzo Hotel, located just within the city walls of Lucca, offers a buffet serving fresh, local produce daily for breakfast. Lucca Cathedral and Guinigi Tower are only 10 minutes away by foot.
See availability and prices here!
Head Over to Pisa and Explore Every Corner of it
When on a Tuscan road trip, you’ll find the cities to be more and more enchanting by the day. Pisa is one of the towns you can’t miss, and you will find yourself in.
There are many things to do in Pisa, and it is a great place to enjoy a Tuscany road trip and stay for a few days.
It’s worth checking out the Campo dei Miracoli, a historic square with a cathedral and, naturally, the Leaning Tower of Pisa.
The Tuscan countryside offers wonderful views and great food that you’ll remember forever—in this case, joining a cooking class in Pisa is a great idea.
What to do in Pisa
- Camposanto
- Cattedrale di Pisa
- Piazza del Duomo
- Place des Cavaliers
- Leaning Tower of Pisa
- Battistero di San Giovanni
Of course, you can always tour Pisa’s most important buildings and landmarks on a guided tour. See more here!
Where to Stay in Pisa
Hotel La Pace
3-star Hotel La Pace is right in Pisa’s downtown. The property is just a 20-minute walk from the Leaning Tower and 80 meters from the train station. It has free Wi-Fi and a hearty breakfast buffet, too.
The hotel offers a variety of services and amenities, including a bar and a TV lounge where you can unwind after a long day away. Guests may also unwind in the hotel’s American bar or drink wine in the TV Lounge.
See availability and prices here!
Grand Hotel Duomo
The Grand Hotel Duomo is a 2-minute journey from the Leaning Tower of Pisa on foot. The bar on the roof terrace offers a panoramic city view. Air conditioning is standard in Grand Hotel’s rooms.
A large outdoor terrace with views of the city and tower and a more intimate dining area provide an ideal place to relax with a glass of wine. Grand Hotel Duomo is only 4 kilometers from Pisa Airport and 20 minutes by foot from the main train station.
See availability and prices here!
AC Hotel Pisa by Marriott
Unlike the other accommodations above, the AC Hotel is located 3 kilometers from Pisa’s old city and 4 kilometers from the Airport. It has a contemporary design and rooms equipped with a minibar.
The rooms have a stylish appearance and an elegant vibe. Every morning, guests may enjoy a buffet breakfast in the hotel’s dining room (recently renovated Technogym WiFi equipment).
In addition, there is a 24-hour fitness center (recently renewed with Technogym WiFi equipment) where visitors can relax and work.
See availability and prices here!
Stop by San Gimignano
San Gimignano is a town that you should definitely include in your Tuscan road trip. It is arguably one of the most iconic destinations in Europe.
The architecture is captivating, and there are many things to do when you visit the historic Tuscan town. The most picturesque attraction is Piazza della Cisterna, a triangular plaza flanked by medieval homes.
Lastly, the Duomo di San Gimignano is a church that dates back to the 12th century. Its chapel has frescoes previously made by Ghirlandaio.
Don’t leave without having a wine-tasting experience!
What to do in San Gimignano
- Tenuta Torciano
- Piazza della Cisterna
- Iglesia de Sant’Agostino
- Piazza del Duomo, San Gimignano
- Town Hall, Picture Gallery, and Great Tower
Where to Stay in San Gimignano
Relais Cappuccina
This lovely new four-star hotel, Relais Cappuccina, is a wonderful starting point for discovering Tuscany. 1.5 kilometers away, you’ll find Relais Cappuccina, a peaceful haven with a big outdoor pool and a high-quality wellness center set among rolling hills.
Relais Cappuccina is a lovely Art Nouveau villa. Enjoy spectacular views from your windows each morning and savor a nutritious, filling breakfast in the bright dining hall. All of Relais Cappuccina’s pleasant rooms come with contemporary comforts such as free WiFi.
See availability and prices here!
Leon Bianco
Leon Bianco is located right on Piazza della Cisterna, which is one of San Gimignano’s stunning squares. It is equipped with a relaxing terrace, perfect to enjoy after driving on your Tuscan road trip.
The restaurant serves a buffet breakfast, and the bar on the terrace serves alcoholic beverages during the summer. The hotel also has a fitness center, billiards room, and pool. You can reach the hotel by driving through Porta San Jacopo’s city gate.
See availability and prices here!
Locanda dei Logi
Locanda dei Logi, located 7 kilometers from Piazza Cisterna in San Gimignano, has free WiFi and a bar with a garden. Every accommodation has air conditioning, which is certainly something to consider. A minibar and kettle are available for guest use. Florence Airport is 43 kilometers from the property.
See availability and prices here!
Don’t Miss Out on Siena
Along the way, apart from visiting Pisa, Lucca, and other medieval towns that are worth exploring, Siena should also be on your Tuscan road trip.
Siena, a town in Tuscany’s central Italy region known for its medieval brick structures, is notable for its architectural variety. The Palazzo Pubblico, a Gothic city hall with a fan-shaped central square called Piazza del Campo located at the Campo, is one of the most important sights in Siena.
The city center features Torre del Mangia, a slender 14th-century tower with sweeping vistas from its distinctive white crown. The historic “contrade” (districts) of Siena extend outward from Piazza del Campo.
What to do in Siena
- Duomo di Siena
- Pubblico Palace
- Tower of Mangia
- Piazza del Campo
- Basilica Cateriniana
- Pinacoteca Nazionale di Siena
Where to Stay in Siena
Four Points by Sheraton Siena
The historic city walls are a 10-minute drive from the Sheraton Siena. The hotel offers free parking, a modern gym, and well-decorated rooms. For dinner, Four Points by Sheraton Siena has a sophisticated restaurant serving traditional Italian, regional Italian, and Tuscan cuisine. For breakfast, there is an international buffet.
The lobby has a stylish bar, a Fitness Center with Technogym equipment, and a sauna. Guests can unwind with a glass of wine in the conservatory beside it.
See availability and prices here!
Hotel Santa Caterina
Hotel Santa Caterina is a few minutes walk from Porta Romana and is within easy reach of many attractions. This small, cozy hotel is located at one of Siena’s medieval gates.
In 15 minutes, you can stroll through town to its heart. Rooms are designed in a traditional Tuscan style, and an en suite bathroom or a separate shower facility is available.
See availability and prices here!
Hotel Palazzo di Valli
The Hotel Palazzo di Valli is another gorgeous property in Siena. It dates back to the 18th century and is conveniently located 400 meters from the historic center. The hotel is set on a hill with 18-acre grounds. The city center is about a 10-minute walk on foot.
See availability and prices here!
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