Last Updated on October 26, 2023 by Ingrid & Alex

Planning the ideal Tuscany road trip itinerary isn’t simple, but it’s well worth the effort. In fact, with endless little cute towns in Tuscany as well as bigger cities that are home to hidden gems, staying a few days are sometimes not enough.

I’ve prepared the perfect Tuscan road trip you should follow whether you stay in the region for a week or a month and 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, and spectacular sunsets and Tuscan wines. Italy is simply one of the best places to visit in Europe and you can’t just 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 making a trip there.

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This is the Perfect Tuscan Road Trip

Explore Florence

7 days in Italy itinerary
Source: Pixabay

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 so that you can see all of 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 as 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 Gallerybook 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. There are multiple rooms that can all accommodate couples or families with children comfortably. All bedrooms have a private bathroom with modern amenities and free wifi. See availability and prices here!

Hotel Lungarno – Lungarno Collection

Lungarno Hotel is the ideal accommodation for all travelers searching for comfort and luxury in a win-win location. There are professional business services available on-site, too. The rooms are bright, welcoming, clean, and spacious. 

There’s a bar and restaurant downstairs and it’s conveniently located near the train station and close to all major attractions like 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

Lucca cathedral
The cathedral of Lucca, in San Martino square.

The beautiful, laid-back Lucca is the ideal first stop on your journey around Tuscany, and it’s 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, and finding parking 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 you find and book the best option for renting a car during your trip, helping you 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 get to see the most important attractions, along with 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.

If you’re planning to stay a few days in Lucca, this is certainly one of the best options.

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 to Porta San Donato. Rooms are equipped with free Wi-Fi and obviously air conditioning should you plan a Tuscan road trip during the summertime. Most rooms here come with traditional wooden floors and bathrooms made up of marble. 

A buffet serving fresh, local produce daily for breakfast is available at The Palazzo Hotel, located just within the city walls of Lucca. Lucca Cathedral and Guinigi Tower are only a 10-minute away by foot.

See availability and prices here!

Head Over to Pisa and Explore Every Corner of it

Italy honeymoon itinerary

When on a Tuscan road trip, you’ll find the cities to be more and more enchanting by the day. One of the towns you can’t miss and you will find yourself in is Pisa. 

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 some wonderful views and great food too 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 go on a guided tour of Pisa’s most important buildings and landmarks. 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 take a glass of 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 situated 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, as well as a more intimate dining area, provides 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

The AC Hotel, unlike the other accommodations above, is located 3 kilometers from Pisa old city and 4 kilometers from the Airport. It has a contemporary design and rooms equipped with as well as 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 to that, there is a 24-hour fitness center (recently renewed with Technogym WiFi equipment) where visitors relax and work.

See availability and prices here!

Stop by San Gimignano

San Gimignano, Italy

San Gimignano is a town that you should definitely include in your Tuscan road trip and is arguably one of the most iconic destinations in all of Europe. 

The architecture is captivating, and there are many things to do when you’re visiting the historic Tuscan town. The most picturesque attraction here 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 with frescoes previously made by Ghirlandaio in its Chapel.

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 to discover Tuscany. 1.5 kilometers away, you’ll find Relais Cappuccina, a peaceful haven with a big outside pool and a high-quality wellness center set among rolling hills. 

Relais Cappuccina is a lovely Art Nouveau villa. Each morning, enjoy spectacular views from your windows 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 has a fitness center and billiards room, as well as a pool. You can get to 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

Florence day trips

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. 

A slender 14th-century tower with sweeping vistas from its distinctive white crown, Torre del Mangia, can be found in the city center. 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. You’ll find free parking, a modern gym, and well-decorated rooms. A sophisticated restaurant serving traditional Italian, regional Italian, and Tuscan cuisine is available at Four Points by Sheraton Siena for dinner. For breakfast, there is an international buffet. 

A stylish bar with a Fitness Center with Technogym equipment, as well as a sauna, is available in the lobby. In the conservatory beside it, you may unwind with a glass of wine.

See availability and prices here!

Hotel Santa Caterina

Hotel Santa Caterina is a few minutes’ walk from Porta Romana and 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 with an en suite bathroom or a separate shower facility available.

See availability and prices here!

Hotel Palazzo di Valli

The Hotel Palazzo di Valli is another gorgeous property in Siena and dates back to the 18th century. It 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 way on foot.

See availability and prices here!

Other Italy travel resources

The perfect 7 days on the Amalfi Coast itinerary

An easy to follow 5 days in Amalfi itinerary

An ultimate Rome and Amalfi Coast 10 days itinerary 

How to get from Rome to the Amalfi Coast – a complete guide!

A perfect 2 days in Cinque Terre itinerary


Tuscan road trip itinerary

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