Europe Travel, Italy

4 Days in Tuscany | 4 Day Tuscany Itineraries

Ah, Tuscany. Italy’s spectacular (and wildly popular) region, home to medieval towns and stunning vineyards. When visiting this beautiful country, Tuscany is a must-see spot on your list!

From the leaning tower of Pisa to the beautiful architecture in Florence, to the medieval city of Siena and the many stunning vineyards sprinkled throughout the Tuscany region, there’s something for everyone here. And it’s a trip you won’t soon forget.

In this post, we’ll be sharing with you our exact 4 day Tuscany itinerary, tips on where to stay, all of the must-see sights, and the best way to travel between cities. 

Let’s start planning your trip to Tuscany!

READ MORE: Should You Visit Rome or Paris?

Jump To:
How to Travel to & Around Tuscany
Tuscany 4 Day Itinerary: Day 1 – Florence
Tuscany 4 Day Itinerary: Day 2 – Siena
Tuscany 4 Day Itinerary: Day 3 – San Gimignano
Tuscany 4 Day Itinerary: Day 4 – Pisa

How to Travel to & Around Tuscany

Both Florence and Pisa have international airports that you can fly into. You’ll then be able to take a train, bus or car to the other cities on this list (or anywhere else you’d like to visit). If you’re used to not taking any public transportation like many of us Americans are, you’ll find that train and bus travel is very common here and if you’re not renting a car, you’re likely to need to take one of them at some point during your trip.

If you’re planning on exploring the small towns of Tuscany or want to spend time in the countryside, you’d likely be better off renting a car so you’re free to see everything you want to see with ease!

READ MORE: The Ultimate Guide to Rome, Italy

Tuscany 4 Day Itinerary: Day 1 – Florence

Florence (Firenze in Italian), is the most populated city in Tuscany and the capital of the region. This iconic Italian city is home to painting masterpieces, incredible Renaissance architecture, and even the famed “David” sculpture by Michelangelo. 

With lots of ground to cover, you may find this is your busiest stop on your trip in Tuscany, and you may even want to spend two days here instead of just one. With historical statues and monuments everywhere, It’s like walking through a giant open-air museum!

Start your day off at the Galleria dell’Accademia where you can see incredible works of art by Botticelli and Da Vinci, as well as the famous David sculpture. Lines can get long here, even though it’s a small museum, so grab skip-the-line tickets in advance to avoid wasting time on your day in Florence! If you’re a major art fan, you might want to grab this tour ticket to see both the Academia and the larger museum, Uffizi.

Walk the city’s main streets and side streets, soaking up all of the Tuscan atmosphere and architecture. Then take a stroll through Mercato Centrale to shop for authentic olive or truffle oil, local cheese, or hand-made sweets to ship home. 

Next up, you’ll want to go see the Piazza del Duomo, home of the Santa Maria del Fiore Cathedral. This is one of the most iconic spots in all of Italy! Enter the cathedral (you can enter for free) and marvel at the incredible architecture. Or grab a ticket to climb to the top of Giotto’s Bell Tower or Brunelleschi’s Dome for amazing views of the city. Get your tickets in advance, especially during high season – we recommend this one!

From the Piazza del Duomo, you can do a quick 3-minute walk to the Piazza della Repubblica. This piazza is the site of the former Roman Forum of Florence, and it was the city center during the Roman Empire. Snap a picture of the beautiful carousel in this square, then continue walking to the Fontana del Porcellino. 

Stick a coin in the mouth of this bronze pig fountain and make a wish as it drops into the grate, if it falls through, your wish is said to come true! Then, as legend has it, if you rub the pig’s nose, you’re guaranteed to return to Florence one day!

Next, we have another piazza! Piazza della Signoria is close by and is home to the Palazzo Vecchio, a beautiful open-air museum showcasing stunning statues, Neptune’s Fountain, and the Uffizi Gallery.

Stroll across the Ponte Vecchio Bridge, one of the most iconic sights of Florence. This pedestrian bridge offers beautiful views of the Arno River, but keep in mind that it can get a little crowded.

Finish the day by watching the sunset from Piazza Michelangelo, back where you started. This is one of the best viewpoints of all of Florence, and an amazing way to end your day in the city. 

Where to Stay in Florence:

Golden Tower Hotel & Spa, new boutique hotel in the heart of Florence, this luxury hotel is the perfect place to rest your head after a busy day out in Florence. Enjoy being walking distance to the Basilica of Santa Maria Novella at the Ambasciatori Hotel Florence. Guests love the historic and convenient location!

HOT TIP: See all of Florence’s top sights with the Florence City Pass! You can check it out here.

Tuscany 4 Day Itinerary: Day 2 – Siena

Centrally located in Tuscany, Siena is famous for its medieval brick buildings and surrounding 1,000-year old wall. As a UNESCO-listed history center, this beautiful city should definitely be at the top of your list when adventuring through Tuscany.

In the summer, they also hold the Palio di Siena, a legendary horse racing competition and one of Italy’s most popular sporting events. Even without the horse races, you can still enjoy seeing the central Piazza del Campo di Siena. This 13th-century square has an iconic shell shape that’s split into 9 downward sloping sections that meet in the center for water drainage. This unique slope also creates a beautiful view of Siena from any angle! 

Next, head to the Pubblico Palace and climb the 400 steps to the top of the Torre del Mangia for panoramic views of the city and its surrounding countryside. This building also houses the city’s civic museum and you can enjoy beautiful works of art here.

Walk to the Piazza del Duomo where you’ll find the Siena Cathedral (or Duomo di Siena). This stunning Roman Catholic Church was built all the way back in 1215 and is the perfect place to admire the city’s ancient architecture. 

When you’re done wandering the beautiful streets of Siena and exploring all of its stunning buildings and squares, go to the Porta Camollia (Camollia Gate) at the north end of the city. Siena is one of the few cities in the world still surrounded by a totally intact medieval wall, and it’s so grand it’s definitely worth seeing!

Next, check out Palazzo Salimbeni, the world’s oldest bank. This 15th century Gothic-style palace overlooks a square that was designed by architect Partini that wanted to create something medieval and renaissance-style for the space. With hundreds of lights filling the interior and square, it’s truly something special to see at night.

Where to Stay in Siena

Stay right near the famed Duomo di Siena at the Il Battistero Siena, with some rooms even having lovely city views.  Just a 5-minute walk from the Torre del Mangia and the Piazza del Campo, the Villa del Sole Siena is another guest-favorite with a great location.

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Tuscany 4 Day Itinerary: Day 3 – San Gimignano

While a small town in Tuscany, this hilly Italian town just southwest of Florence has a lot to offer! Surrounded by 13th-century walls, this medieval town has a beautiful triangular square lined with ancient houses at its center, called the Piazza della Cisterna. Explore the old-world streets and take in the views of medieval towers – there are 14 of them – including the famous stone Torre Grossa, the tallest tower that still remains here. 

Known as Italy’s Medieval Manhattan, you can make your way through the city on foot or by vespa. From Torre Grossa in the Piazza delle Erbe, you can walk up the hill to La Rocca di Montestaffoli. This is the ruins of the 14th century fortress situated above the town. Here, you’ll find shady olive groves and beautiful views  of the rolling Tuscan hills. In the summer, there’s even an outdoor cinema here where you can watch movies!

Next, for wine lovers, you’ll want to learn about Tuscany’s best white wines at the Vernaccia di San Gimignano Wine Experience, the local wine museum. Or you can book a wine tour at one of the local wineries to have the full Tuscan wine experience!

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Where to Stay in San Gimignano

Set in a former monastery, Hotel La Collegiatais a stunning and unique property in the heart of Siena. You may also want to check out Hotel L’Antico Pozzo, a 17th-century convent situated on a narrow pedestrian street just a 4 minute walk from the city center, Piazza della Cisterna – a location that’s very popular with first-time visitors and seasoned travelers alike. 

Tuscany 4 Day Itinerary: Day 4 – Pisa

It might be an obviously touristy spot, but if you’re here, you have to go see the Leaning Tower of Pisa! This iconic tower built in 1372, was already leaning when it was completed. As a bonus, you can climb to the top for beautiful views over the rooftops of Pisa.

While you’re there, wander around the Piazza Dei Miracoli, which is the square where the Leaning Tower is.  

Here you’ll see beautiful architecture, the Pisa Cathedral and Camposanto Monumentale. All of the buildings are open to the public so you can check out the interiors as well. 

Explore the Camposanto, a massive cemetery built in 1277 next to the cathedral. It’s even said that the soil here came from Jesus’s place of crucifixion! Be sure to check out its stunning interior courtyard with regal columns and arches that feel like a step back in time.

Then, explore the charming cobbled streets of Pisa, do some shopping and walk along the River Arno. 

Don’t forget to enjoy all of the traditional Tuscan food to really soak up your experience in Pisa!

Where to Stay in Pisa

With it not being a huge city, most of the sights are concentrated in the Santa Maria area near the Leaning Tower of Pisa. This is where you’ll also find charming cobblestone streets, cute boutiques for shopping, and great restaurants.  If you want to explore on foot, or just be near the sights so you don’t have to take buses around, the Santa Maria area is an excellent choice. Check out The Rif luxury hotel for a relaxing, high-end experience or the Grand Hotel Duomo for stunning rooftop views and the AC Marriott Hotel Pisa for fantastic yet affordable accommodations.

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