• MONTEFIORALLE (Greve in Chianti)

Montefioralle, listed among the "100 Most Beautiful Medieval Villages in Italy," dates back to the 11th century and was once a key defensive stronghold. Its well-preserved stone walls and towers still offer stunning views of the Chianti region. The village is the birthplace of Giovanni da Verrazzano, the explorer who discovered New York Harbor in 1524. A plaque marks his birthplace near the village square.

The Church of Santa Maria, built in the 11th century, features Romanesque architecture and beautiful frescoes. Legend says the name "Montefioralle" comes from "Mons Floralis," meaning "Mountain of Flowers," a nod to the surrounding lush landscape.
Take about an hour to explore its narrow streets, historic buildings, and breathtaking views—an authentic taste of Tuscany’s past.

• PANZANO IN CHIANTI

Panzano is a peaceful town nestled in the heart of Chianti, where you’ll find yourself admiring the stunning blue-green valleys and fiery sunsets. It’s home to the renowned butcher Dario Cecchini, whose shop is a must-visit. The town is also dotted with wineries, making it a perfect stop for wine lovers.

Allow about 2 hours to explore its charming streets, soak in the views, and perhaps enjoy a taste of local delicacies and wines.

• RADDA IN CHIANTI

Radda-in-Chianti is a picturesque town with a historic castle, located in the heart of the Chianti Classico wine region. Known for its deep wine heritage, it was once the administrative center of the Chianti League during the Middle Ages. The town’s main square, Piazza della Repubblica, features the beautiful Palazzo del Podestà, a medieval building that still serves as a symbol of Radda’s historical importance.

The surrounding vineyards produce some of the finest wines in the Chianti Classico region, including the famous Chianti Classico DOCG. Spend about 2 hours exploring Radda’s narrow streets, visiting the wine cellars, and taking in the breathtaking views of the rolling hills and vineyards.

• CASTELLINA-IN-CHIANTI

The charming town of Castellina in Chianti offers stunning landscapes, locally crafted gelato at Gelateria di Castellina, and panoramic views from the historic Rocca di Castellina. The Rocca, a 14th-century fortress, provides a spectacular vantage point over the rolling vineyards and olive groves of Chianti. Take your time to explore the medieval streets, visit the Archaeological Museum of Chianti, and indulge in the local treats. Allow around 3 hours for a leisurely visit to fully enjoy its beauty and history.

• VOLPAIA

Volpaia is one of those hidden gems in the Chianti hills, where time seems to slow down. The village dates back to the 11th century, and you’ll feel its history as you wander through the narrow stone streets. It’s quiet, with beautiful views of the vineyards and olive groves that surround it.

If you enjoy wine, it’s worth stopping by the local winery, where they make some of the best Chianti Classico. The Chiesa di San Donato is also a lovely spot to visit. We’d recommend allowing about 2-3 hours to explore at a leisurely pace and take in the peaceful atmosphere.

• SAN GIMIGNANO

San Gimignano is famous for its impressive medieval towers, which once served as symbols of wealth and power. The town offers breathtaking views from the top of Torre Grossa, where you can see the surrounding countryside stretching out below. As you explore its charming streets, don’t miss the chance to stop for some of the best gelato you’ll find in Italy.

The town’s medieval architecture, along with the Collegiate Church of Santa Maria Assunta and its beautiful frescoes, adds to the experience. Plan for about 4-5 hours to wander at a relaxed pace, enjoying the views, history, and the lively atmosphere.

• SIENA

Siena is one of those places that quietly steals your heart — not with grand gestures, but with warm terracotta tones, medieval streets that twist like ribbons, and a sense of time standing still. Just an hour from Il Cascino, it’s close enough for a day trip, but rich enough to linger in your memory much longer.

At the heart of Siena is Piazza del Campo, one of the most beautiful squares in all of Italy. Shaped like a scallop shell, it once hosted medieval markets and celebrations — and still does, in a way. Twice a year, on July 2 and August 16, the square becomes the stage for the Palio di Siena, a bareback horse race like no other. Ten riders, representing different districts (contrade), charge around the square at dangerous speed, cheered on by thousands. It’s loud, chaotic, and deeply emotional — a centuries-old rivalry that turns the whole city electric.

To start your visit smoothly: leave your car at the Santa Caterina car park just outside the historic centre. From there, a series of escalators (yes, really!) carry you up the hill straight into the heart of old Siena. It’s not just practical — it’s almost theatrical: you emerge into the past without breaking a sweat.

The car park is named after Saint Catherine of Siena, one of Italy’s patron saints, born here in 1347. She wasn’t a noblewoman or a cloistered nun — but a determined young woman who defied expectations, advised popes, helped bring the papacy back to Rome, and was later canonised. Her house is now a small sanctuary you can visit — humble, peaceful, and deeply moving.

Once in the city, don’t miss the stunning Duomo, striped in black and white marble, like a zebra in stone. Step inside and look down — the floors are artworks in themselves, some only fully revealed in September and October. Visit the Piccolomini Library, climb the Facciatone for breathtaking views, and wander the narrow streets where each contrada has its own symbol — owl, unicorn, snail, dragon — and fierce local pride.

For a true taste of Siena to take home, look for panforte — a dense, spiced fruit cake that’s been made here since medieval times. Originally a gift for nobles and pilgrims, it’s now one of Siena’s most beloved traditions, wrapped in old-fashioned paper and rich with almonds, honey, spices, and history.

Siena is a place best explored slowly, with no real destination. Let yourself get a little lost. Sit with a coffee in Piazza del Campo, watch the sun shift on the stones, and imagine all the centuries that have passed under your feet.

If you’re thinking of capturing your trip in a special way, consider bringing along a photographer — it makes all the difference. We visited Siena with Karina, and thanks to her, we have a whole album full of beautiful moments.

• FLORENCE

Florence can feel like a dream you’ve stepped into — all golden light, Renaissance facades, and the scent of leather and espresso drifting through sunlit streets. It’s a city of masterpieces, yes — but also of tiny corners, local secrets, and the kind of quiet beauty that sneaks up on you when you're not looking.

You can park conveniently at the Parcheggio Sant’Ambrogio, just a short walk from the heart of Florence. If you want to avoid driving into the ZTL zone, another option is to drive from Il Cascino to Villa Costanza via the highway, park there, and take tram number 1 into the city — it runs frequently and is super convenient.

The Uffizi, the Accademia, and the Duomo are icons for a reason — standing in front of Botticelli’s Birth of Venus or Michelangelo’s David is unforgettable. But once you’ve had your fill of crowds and masterpieces, turn your steps somewhere quieter.

One of our favourite lesser-known treasures is the San Marco Museum, a peaceful, sun-drenched former monastery where Fra Angelico painted frescoes directly onto the monks’ cells. There’s something deeply moving about the silence of the space, and the light that seems to linger on the painted walls. It’s not grand, it’s just… human.

And then, cross the Arno to Oltrarno, the "other" side of Florence. Here, the streets are a little sleepier, the people less hurried. Stop in Piazza Santo Spirito, where locals gather in the evenings with glasses of wine and easy laughter. It’s a bit scruffy, a bit soulful — and full of life.
Speaking of wine: we love "Le Volpi e l'Uva", a small, warm enoteca where the wine list is lovingly curated and the conversation flows easily. The kind of place where one glass turns into two, and you start planning your next trip before you’ve even left.

For a truly unforgettable gelato, don’t miss Gelateria della Passera — tiny, tucked away near Piazza della Passera, but worth hunting down. The flavours change daily and are made with care and creativity (think fig with ricotta, or dark chocolate with red wine). It’s where locals go — and that tells you everything.

Florence is beauty layered on beauty, but what stays with you isn’t just the art. It’s the warm light on a stone wall at sunset. The quiet hum of footsteps on old cobbles. The clink of glasses in a tucked-away piazza. And that perfect, melting spoonful of gelato when you least expect it.

Let the city show itself to you, not just in its museums — but in its shadows, sips, and silences.

We explored Florence with Olya, and if you’d like, you can also book a photoshoot with her to capture your own beautiful moments around the city.