Last Updated on July 7, 2024 by Tori’s VA
If you are planning a weekend trip to Tuscany, there are plenty of great things to fill your days with. From visiting cultural attractions to going on bike trips through the idyllic Tuscan countryside. Tuscany is a dream destination for so many and not without a reason.
There are endless rolling hills covered in vineyards and topped with hilltop towns overlooking it all. It is easy to get taken back to Medieval times as you stroll through old, cobbled streets with ancient stone houses closing around you, the delightful scent of Italian food cascading out of traditional trattorias, and warm streetlights in the evening casting shadows into old alleyways.
A weekend in Tuscany is doomed to be great. In this itinerary we will take you to some of the best towns in Tuscany. Including the region’s incredible capital city, Florence.
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Weekend in Tuscany Map
Where to stay in Tuscany
When spending a weekend in Tuscany, your best bet is to stay in Florence the entire weekend. Then travel from there. The places you will visit on this itinerary are quite close to Florence. So you can easily return to Florence at night. This is also a great excuse to have some nice Tuscan wine in Florence at night and get to know the city a little more. After all, it is known as the Cradle of Renaissance and it has a vibe like no other city.
When looking for where to stay in Florence, the historic center is great for easy access to all the main attractions by foot. If you want a more local vibe, the Oltrarno neighborhood is a favorite among return visitors.
Here are some of the best hotels to stay for every budget:
LUXURY: Palazzo Portinari Salviati Residenza D’Epoca
MID-RANGE: B&B La Terrazza Sul Duomo
BUDGET: B&B Alla Corte dei Medici
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How to get around in Tuscany
The best way to get around Tuscany for only a weekend is by renting a car at Florence Airport. This gives you the flexibility to see more places in a shorter amount of time. Otherwise, I suggest you book a guided tour from Florence for the second day of this 2 days in Tuscany itinerary. This way, you can see a couple of towns besides Florence. You can also use the car to explore more of Italy, which I cover in my 2 week Italy trip itinerary.
However, the organized tours do not give as much flexibility as driving yourself. Yet some private tours might give you some of the flexibility you want. If you opt for a tour, make sure you book it as early as possible to ensure that you get the tour options that you prefer.
Best time to go to Tuscany
Tuscany is a wonderful destination all year round. However, there are some differences between the seasons that you should consider before deciding what time of the year you prefer for a weekend in Tuscany.
Summer is the high season and gets very crowded and temperatures rise above 86 degrees Fahrenheit. If you find this too hot, you will be delighted with the fall and spring temperatures of around 68 degrees Fahrenheit in the daytime. It is also slightly less crowded as you avoid the big European holiday months of July and August. Yet, especially spring, is a very popular season especially for the temperatures and mild weather. Tuscany is especially romantic this time of year, so bring your special person and fall in love with each other and this magical place.
In the winter, Tuscany might get snowfall, though is hardly ever sticks. The temperatures are cool, but the holiday spirit will warm you. And it is the perfect time of the year to experience this incredible region in the festive season.
2 Day Tuscany Itinerary
Weekend in Tuscany Day 1
Spend your first day in Tuscany by exploring Florence. The capital of Tuscany doesn’t lack things to see and do. Make sure you start your day early with a good breakfast, because this day will be jam-packed with exciting experiences. Note that some of the below things must be booked in advance and will have a set entry time. Make sure you plan your itinerary early by purchasing tickets and tours so you can get the times you prefer. Otherwise, this itinerary is easy to swap around on things to make it work for you.
If you arrive early on the Friday, make your way up Piazzale Michelangelo for sunset.
Visit the Duomo
First, head to Florence’s most prominent landmark, the Duomo, also known as Cathedral of Santa Maria del Fiore. The impressive basilica is even more impressive on the inside. With beautiful, tiled floors, majestic columns, and stained-glass windows. Further, the cathedral is home to several masterpieces by Michelangelo, Giotto, and Donatello. Not to mention the impressive frescoes in the cupola. But more about them later.
The Duomo was built between the late 13th century and the early 15th century on top of a small church from somewhere between the 4th and 6th centuries. You can see the remains in the museum below the basilica.
You can climb the clock tower for views of the cathedral and the rest of the city for a fee. But I recommend spending your time wisely and instead climb the cathedral’s dome.
Climb the Cupola
The dome of Florence Cathedral is one of the highlights of the city and requires a separate ticket to climb. The 463 steps take you to one of the most spectacular views of Florence. But besides offering sweeping views of the city, the main highlight is on the way up.
Walking up the stairs you will get a closer look at the impressive frescoes inside the dome, painted by Giorgio Vasari and Federico Zuccari. The colorful paintings make up an incredible art piece and an excellent introduction to Florence’s reputation as an artistic hub.
You can book a tour or just book the dome climb.
See David in the Accademia Gallery
Depending on how hungry you get, go for lunch either before or after the Accademia Gallery. This is where Michelangelo’s masterpiece, David, is exhibited. While you will see him several places in Florence (and in other Italian cities,) this is the original and the one you want to see.
Besides David, there are several interesting art pieces by other Florentine artists. Among the most famous pieces you can see are the Coronation of The Virgin by Jacobo di Cione and Slaves by Michelangelo.
Book a guided tour to learn as much as possible. Or buy tickets in advance without a tour.
Go for a bike trip
Next, take a bike trip to explore the countryside around Florence. There are plenty of bike trips in Tuscany leaving from Florence. But I especially recommend wine tasting at a vineyard to get the Tuscan experience.
Cycling tours typically last 3 to 4 hours. And if you prefer e-bikes there are opportunities to book that too, saving you plenty of energy. If you prefer going on your own without a guide, you can rent bikes or e-bikes too. It is refreshing to get out of the city and get a taste of the Tuscan countryside.
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Stroll around the historic center
Round off your first day in Tuscany by strolling around the historic center and take in the incredible atmosphere of Florence. The entire historic center is a UNESCO World Heritage Site, so you can only imagine it is worth spending time there.
Make sure you cross the iconic Ponte Vecchio which was the only bridge that survived the bombings of World War 2 on the Arno River. Now, it houses jewelry shops and antique shops where you can find interesting items to bring home. You should also check out the bridge from the next bridge for a better view of it (it is such a cute bridge!)
There are plenty of restaurants, trattorias, and bars in the historic center where you can have a nice dinner accompanied by a nice glass of Tuscan wine. But make sure you do not go overboard with the wine as tomorrow you have another long day in Tuscany!
Weekend in Tuscany Day 2
Visit San Gimignano
Start your day by driving to San Gimignano, a medieval hilltop town near Florence that’s surrounded by vineyards. It does not get much more idyllic than this. It takes just over an hour to drive to San Gimignano from Florence. You can spend 2-3 hours walking around the town and grab a coffee and pastry taking in the ambience.
The main attraction in San Gimignano is climbing the 13th-century Torre Grossa, the highest of the remaining towers, for a bird’s eye view of the terracotta rooftops leading to endless rolling hills covered in vineyards. There were once 72 towers in San Gimignano and some reached an altitude of more than 50 meters. Only 14 of those towers have survived until today. Yet, the Tuscan town is nicknamed the Manhatten of Tuscany due to its medieval “skyscraper” skyline.
The Town Hall is home to exceptional frescoes by artists like Lippo Memmi and Memmo Di Filipuccio. Next door you find the majestic San Gimignano Cathedral whose interior is covered in 14th-century frescoes telling the tales of both the Old Testament and the New Testament.
San Gimignano’s oldest fort is Rocca di Montestaffoli. The remains are not that great, but if you have time, it is worth heading there for the views. Otherwise, getting lost in the streets, go shopping for local handicrafts, and taking pictures is a great way to spend the time in this traditional Tuscan town.
Discover Monteriggioni
Continue to Monteriggioni. This is a small (and I mean small) walled town on the way to Siena that you can easily see in an hour or less. It is a good place to stop for lunch and go for a stroll through the streets. The little hamlet was built in the 13th century as a frontline by the Sienese to protect their land from the Florentines. Now, it is considered one of Italy’s best preserved medieval towns and it is a true little gem.
There is a large public parking outside the walls where you can leave your car when walking into the interior of the walls.
End the Day in Siena
Continue your weekend in Tuscany with a final stop in Siena, which is another spectacular medieval city. Depending on when you arrive, there are several attractions you can see, but here are the top sights I suggest you choose from. First, the Mangia Tower on Piazza del Campo, Siena’s iconic shell-shaped square which is an attraction itself with plenty of restaurants and bars. The tower offers sweeping views of Siena and is found in the Civic Museum.
The Duomo in Siena
This is a good alternative combined with strolling through the old town if you get to Siena late. However, if you have time, the Duomo complex of Siena is a must visit, but it requires at least 2-3 hours to see everything. The cathedral dates back to the 13th century and is an exquisite example of Gothic architecture. But the basilica is not fully completed.
It is possible to climb up to the top of the church for city views, which is highly recommended as you get sweeping views of Siena including the Mangia Tower. The floors of the cathedral are covered in beautiful mosaics and stained glass windows bring warm light into the forest of columns.
Besides the cathedral, you will see the Museo dell’ Opera where several sculptures by artists like Giovanni Pisano. Beside other original art pieces from the cathedral, you can see Duccio di Buoninsegna’s impressive stained-glass rose window.
In 1999 the crypt was uncovered during restoration work. It dates back to the 12th century and you can see incredible medieval frescos there.
Finally, the Piccolomini Library is one of the most impressive places in the complex. The colorful frescos that cover the walls and ceiling depict Pope Pius II’s life and was built to protect the pope’s large book collection.
If you don’t get time to enter the complex, make sure you get a picture from the outside at least to see the beautiful building.
After a long day exploring Tuscany, head back to Florence, or continue driving south for a few days in Rome.
If you have more time
There’s many other incredible things to do and places to see in Tuscany. Here are some of my favorites.
- Take a cooking class in Florence
- Soak in the Saturnia Hot Springs
- Visit the Leaning Tower of Pisa
- Wine Tasting at Tenuta Torciano
- Relax in the parks in Lucca
Conclusion: 2 Days in Tuscany
Summing up a weekend in Tuscany is far from enough to see everything, but it sure gives you time to get a good taste of the art, the culture, and the food. And not to mention the wine! With careful planning, you get quite a lot done in only a weekend and if you feel like slowing it down a bit, feel free to skip any of the above-mentioned activities. That said, with this itinerary you get a great introduction to the best of Tuscany in only a couple of days and I am sure you will start planning your next trip to this idyllic Italian corner.
