Penthouse Serena Tuscany

24/09/2026

YACHT SERENA
Whales on the horizon, a dolphin es**rt off the bow, and some of the best sailing in the world. Add snorkeling, a fresh catch, a guitar on deck, and a new anchorage each evening, and you have life aboard Yacht Serena.

Let Captain Hugh and Chef Vivi spoil you. They are both chefs, so every menu is created around you, right down to the Serena Slings. Hugh takes care of the sailing and the island know-how, and keeps you entertained with his stories (a book is definitely in the making). All you have to decide is how much of each day belongs at the helm and how much to simply stretching out on deck.

Fun for every age: little ones spotting turtles, teens taking the wheel, grown-ups lingering over sunset cocktails.

Now booking 2027–2028, and Christmas/New Year's 2026 is still open. Message us to start planning your charter.

21/09/2026

This morning, Montepulciano closed its Bravio delle Botti season the way it does everything: with drums, flags, and centuries of tradition in the streets. The corteo storico passed directly beneath Penthouse Serena on its way to the Santuario di Sant'Agnese, and we watched from the church steps just across from our door. That is what staying in the historic center means — the town's great occasions pass right in front of you.

At this afternoon's closing ceremony, the Arca d'Argento for the finest historic court costumes and characters went, fittingly, to our contrada — Gracciano, whose name our own street carries. Until next August, Montepulciano!

Ask us about staying in the heart of the historic center during next year's Bravio.

18/09/2026

We spent yesterday chasing rainbows through the countryside below Montepulciano. The sun broke through while the rain was still falling, and suddenly there were two of them arching over the vineyards — the town itself on the hilltop in the distance. We stopped the car and simply stood there.

The vendemmia is underway. Some of the Prugnolo Gentile grapes — the local Sangiovese that becomes Vino Nobile di Montepulciano — have already been picked, while others still hang heavy on the vines, waiting their turn. After two days of generous rain, the hills are green, the air is washed clean, and the whole valley feels caught between summer and harvest.

This is the season we love most at Penthouse Serena: the heat waves of summer break, the rains come, and the air fills with the scent of rain and rich earth. Message us if you'd like to visit Montepulciano during the vendemmia.

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 b**r 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 w**e 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.

Message us for available dates.

Send a message to learn more

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. 🤍