Penthouse Serena Tuscany

04/09/2026

One night in Florence before flying to Berlin to visit my daughter Esmeralda.

We began with aperitivo at Rivoire on Piazza della Signoria — a Negroni for me, Italian beer for Captain Hugh — looking out at David and the Fountain of Neptune as the piazza slowly lit up for the evening. There is something about that square at night: the statues glowing, the day’s crowds thinning, the whole city settling into itself.

Then a short walk through the old streets to Trattoria del Chianti for a proper bistecca alla Fiorentina, done exactly as it should be.

For our Penthouse Serena guests: Florence is only about an hour and a half from Montepulciano, and we are happy to arrange a private driver — for a full day among the museums and piazzas, or an evening of aperitivo and dinner, with no one counting the Negronis.

Some cities reward even the briefest visit — Florence most of all.

28/08/2026

This is the Montepulciano we call home ❤️ CBS Sunday Morning’s look at the Bravio delle Botti — the wine barrel race between our eight Contrade, happening this Sunday.

Traditions like this are why guests fall in love with this town!

27/08/2026

The Bravío delle Botte 2026 festivities continue this week! The big event is on Sunday ✨✨✨

08/08/2026

Style isn’t about where things come from. It’s how they come together.

A hand-thrown ceramic beside a stack of well-read books. An antique green iron table on the rooftop terrace. Art, objects, and a little whimsy, arranged so that every room tells its own story.

This is our home in the heart of Montepulciano — and when you stay here, it becomes the backdrop for a story of your own.

Stay somewhere personal.

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26/07/2026

This is exactly how we hope every guest feels at Penthouse Serena Tuscany — and at all our Serena properties. Thank you, Glenn and Lee, for these kind words about your June stay:

“The Penthouse Serena was fabulous! You truly feel like you are in a home…a beautiful home!! The rooftop terrace was absolutely gorgeous and a great place to share a dinner or aperitivo! The sound of the church bells was both soothing and comforting. Gabriele could not have been nicer or more patient…he even waited for us when our train was delayed! The smell of the bath towels and sheets was heavenly. We absolutely recommend this AirBnb when visiting Tuscany!” — Glenn and Lee, Maryland, U.S.A.

The terrace at dinner, enjoying our eclectic and interesting decor, an aperitivo above the rooftops — these are the everyday moments that make our apartment feel like home. And yes, we are very grateful to have a wonderful property manager like Gabriele, who takes such good care of our guests.

Contact us for available dates.

08/06/2026

Perched high above the vineyards, olive groves, and breathtaking landscapes of the Val d’Orcia, Montepulciano is one of Tuscany’s most enchanting hilltop towns.

Wander its medieval streets, savor a glass of its world-famous Vino Nobile on our rooftop terrace, and experience the timeless beauty of Tuscany.

Book your stay at Penthouse Serena Montepulciano and make this extraordinary corner of Italy your home away from home.

A Serena Group property.

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27/05/2026

A magical morning in Montepulciano as the magnificent Tempio di San Biagio emerges from a sea of fog. ✨

Built beginning in 1518 by Renaissance architect Antonio da Sangallo the Elder, this architectural masterpiece was commissioned after a local fresco of the Madonna was said to have performed a miracle, drawing pilgrims from across the region. More than 500 years later, San Biagio still inspires awe.

On mornings like this, with the church rising above the mist of the Tuscan countryside, it’s easy to understand why. 🤍

11/05/2026

There’s something special about slow mornings on the rooftop terrace at Penthouse Serena—breakfast with a view, a lovely home to settle into, and the magic of Montepulciano just outside the door. We’re so happy our guests from the Netherlands fell in love with both our home and this beautiful town. ✨

29/04/2026

Meet Gabriele—your amazing host at Penthouse Serena, captured here on our terrace above Montepulciano.

Warm, attentive, and deeply connected to the rhythm of the town, he ensures your stay feels effortless from the moment you arrive.

From local recommendations to seamless check-ins, he’s always just a message away.

18/04/2026

High above the rooftops of Montepulciano, a quiet guardian has been keeping time for centuries…

Pulcinella — the mischievous, masked figure from the Italian Commedia dell’Arte — strikes the bell each hour from atop the tower beside Sant’Agostino. First placed here in the 16th century and later transformed into the iconic Pulcinella we see today, his presence remains a mystery. Some say a Neapolitan priest brought him here in the 17th century as a tribute to his homeland… others say he was chosen as a nod to theater and storytelling.

What we do know is this: he has been marking time for the town ever since — a whimsical symbol of tradition, culture, and a touch of Italian irony.

We fell in love with him the moment we saw him — his right hand in motion, his beat echoing over Montepulciano’s rooftops.

At Penthouse Serena, we live just beside him… close enough to see his silhouette and his backside from our terrace — a daily reminder that time here moves differently.

He became part of our story.
And that’s why Pulcinella lives on in our logo.