Tuscany for the first time? 4 essential destinations to explore.

I. Firenze

Driving from Rome, through fields, vineyards, castle ruins, and narrow —almost alley-looking streets —we arrived to the beautiful city of Firenze (or Florence, in English), one of the most visited cities in Italy and the heart of Tuscany, known for its unique architecture, Renaissance art, and history.

Anyone who drives through its streets —first and foremost can literally drive anywhere they want in the world, due to the complexity of the one lane, two way street situation—will also be able to enjoy centuries old buildings, giving a time machine like feeling, transporting you to another era. I can totally imagine myself in a convertible with a scarf wrapped around my head, wearing cat-eyed sunglasses cruising through streets filled with designer boutiques, hidden gardens and sculptures peeking out behind colorful doors with stunning door knockers.

Although having a car is essential for a road trip—which is what we did— parking in this particular city can be somewhat tricky, and you can really get around without a vehicle.

After some searching, we arrived at our Airbnb for the first part of our stay. It was very spacious, with a quirky bathroom and like most Italian accommodations, it had windows that looked over to narrow alleys and internal courtyards where small balconies and clothes hanging out to dry added to the charm.

Il Duomo di Firenze.

We headed to the Cathedral of Santa Maria del Fiore, which is one of the top attractions of the city and a marvel of the Renaissance. Renowned for its dome, it’s typically called Il Duomo di Firenze. The cathedral stands out with its unique marble exterior in pink, green and white. Our original plan was to climb to the dome and check out the city views, however, at the time we arrived the line was overwhelming. So instead, we spent some time around la Piazza del Duomo and had a lovely lunch with a few spritz. The square is a beautiful place to explore, filled with souvenir stands, cafes, gelaterias and shops.

Galleria dell’Accademia.

Easily, this could have been one of the most anticipated sights of the trip, due to our obsession with Michelangelo’s David. One of the most famous sculptures of Renaissance art, it depicts the biblical hero that defeated the giant Goliath throwing one single stone at him. What stands out the most about this masterpiece is the level of detail in the anatomy of David; its muscles, veins, and posture, giving it a real life quality. It stands magnificently in the middle of a hall named after him, where we can all admire its grandeur, accompanied by other unfinished sculptures.

The museum houses many other works of art of the Renaissance period including religious paintings, altar pieces and numerous sculptures from various artist, highlighting Michelangelo’s legacy.

It is recommended to purchase tickets for this museum in advance and make a reservation to avoid lines and ensure a smooth entrance. I also found that their gift shop was great and brought a little bit of Florence back home.

Outside the museum, there were cool shops, and just a few steps away we found an enoteca with a street window serving Chianti Rose, the region’s specialty. These windows actually date back to the 16th century, and although there are fewer today, they still have a lot of charm and show a bit of history of the city. The window was part of a cute restaurant that also had some outdoor tables. We, of course, enjoyed our glass in the middle of the street while chatting and laughing.

Ponte Vecchio.

The night was young, and it seemed like every piazza was filled with people dancing to live music and just caught up in the magic of the city . As the sun sets, Ponte Vecchio transformed into an enchanting, kinda romantic place. The bridge is beautifully lit, casting a warm golden glow into the Arno river below. The bridge is filled with jewerly shops, art dealers and souvenirs stalls, a perfect blend of history and modern-day commerce. The area boasts some of the most elegant and high-end restaurants in Florence, where you can indulge in fine dining while enjoying stunning views. The bustling streets around the bridge often host street performances and add to the city’s vibrant atmosphere. One performance that stood out was an opera singer with a powerful voice echoing through the piazza providing an unexpected yet unforgettable touch of culture and drama.

Four Seasons Hotel Firenze

While in Florence, we got the opportunity to get to know the Four Seasons, and I must say, t’s one of the most luxurious and extravagant properties I have ever encountered. It is a palace-like experience, seamlessly offering historic grandeur and modern sophistication. The hotel occupies two beautifully restored historic buildings: 15th century Palazzo della Gherardesca and the Palazzo Nero. The property is surrounded by lush, expansive gardens, providing a tranquil oasis just moments away from the city’s top attractions. 

The interior design of the property is nothing short of spectacular, featuring polished marble floors, walls adorned with frescoes, imposing sculptures and elegant chandeliers. Guest rooms were spacious, with classic furnishings, marble bathrooms with deep soaking tub and every amenity you could possibly need.

We enjoyed refreshing mimosas, fresh fruit and chia pudding, along with a variety of breakfast selections at Al Fresco and Pool Tree Bar. Afterwards, we took a stroll through their private garden and enjoyed their outdoor pool, stunning works of art, a beautifully designed dome, exotic fruit trees, fountains and cute seating options scattered around the space.

II. Pisa

We continued our day and hopped into the car to embark on the next destination of our beloved road trip through Tuscany. Our first and brief stop was Pisa, where we got to see its iconic leaning tower. This freestanding bell tower of the cathedral is perhaps one of the most famous buildings in the world. Its tilt has made it one of the most recognized architectural oddities. Visitors can climb the 297 steps to the top for breathtaking views of the city. Currently the entrance is about 26,50 euros.

The towers construction started in 1173 and took almost 200 years for its completion. It began to lean shortly after construction due to a poorly laid foundation. Over time, the lean increased considerably. Efforts to correct the lean started in the 90s and in 2001 the lean was reduced at least 1.5 degrees and stabilized it to a safe level so it reopened for visitors.

The leaning Tower of Pisa is a white and grey marble structure with eight stories, including a chamber with seven bells at the top. The tower was designated a UNESCO World Heritage Site in 1987.

Around the tower, you will find plenty restaurants, souvenir stalls and pizza places.

III. Cinque Terre

As you travel from Pisa towards Cinque Terre, you’ll pass through the foothills of the Appenini. These mountains offer stunning views with forests, and winding roads.

Cinque Terre is a stunning stretch of coastline in Liguria, Italy —so far, my favorite place in the country. While this place isn't technically in Tuscany, it's a nearby region that's easily accessible during a road trip through the area. Its name translates to '‘five lands’’  in English, and it’s famous for its picturesque towns perched on cliffs overlooking the Mediterranean Sea. The region is known for its colorful tightly packed buildings, dramatic sea views, and charming atmosphere. You can explore the towns by train or ferry, and for the hikers, there is also a trail that connects all five towns.

The five towns of Cinque Terre are: Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso Al Mare.

On this trip we got the chance to explore Manarola and Monterosso al Mare.

Manarola

This iconic town is famous for its colorful stacked houses sitting on cliffs. It’s nestled in narrow alleys and surrounded by terraced vineyards, with shops selling linen, hats and jewerly. The town also offers breathtaking views from everywhere you look. We walked all the way to a park that provided incredible views of the water, boats and rock cliffs, where we saw people diving from the peak. Up here we found a street vendor and bought beautiful rings. Down at the bay, you can take the ferry to visit the other towns.

Monterosso al Mare

Monterosso is the largest of the five towns, and it has the most extensive beaches, making it popular for swimming and sunbathing. The town is divided into two parts: the old town, with its narrow streets and historic buildings, and the newer part, which has a lovely beach promenade. On the day we visited, it was the harvest moon, which we enjoyed from the beach after sunset.

IV. San Gimignano

The final stop of our roadtrip was San Gimignano, a medieval hilltop town between Florence and Siena. It’s famous for its towering medieval structures, historic charm and impressive well mantained architecture. The historic center is a UNESCO World Heritage Site, known for its well-preserved medieval streets, squares and buildings. Walking through town feels like stepping back in time, with narrow alley ways and charming piazzas.

We wandered the streets, explored its shops, tried a delicious restaurant and indulged in gelato before heading to Rome for the next part of the adventures.