The Val d’Orcia area south of Siena is one of the most beautiful places to visit in Tuscany. In fact, the entire area has been named a UNESCO world heritage site. The region is characterised by harmony and perfection from its slow produced foods, its world famous wines and its balanced and elegant Renaissance buildings. If you’re headed to Montepulciano or Montalcino, don’t miss some of the amazing places in between.

The Perfect Vespa spotted in Montalcino.

When to Travel?

This region is gorgeous at any time of year but September and October are ideal months to visit the Val d’Orcia. Many of the grapes are being harvested and the weather is less hot. Plus you can experience the countryside with perfect fall colors.

View from San Biagio outside Montepulciano

Day One

Montepulciano

Montepulciano has a little bit of everything you could want from a visit to a medieval hillside town including amazing views of the Val d’Orcia region.

Piazza Grande in Montepulciano. On the left the Church of Santa Maria Assunta with unfinished facade.

Wine cellars you can visit for free to check out the enormous wooden barrels where they produce their famous reds.

Cantina Contucci right next to Piazza Grande.

We stopped in at Cantina Cantucci and Talosa Cantina both of which allow you to descend into their cellars for a look around or have a tasting.

Montepulciano is famous for its red wines like Vino Nobile di Montepulciano.

Medieval squares and lanes (with plenty of shopping).

And an absolutely unparalleled view from the tower of the Comune di Montepulciano in Piazza Grande. Go before sunset for the best light!

Church of San Biagio

If you are in the vicinity of Montepulciano, you must stop at this incredible church just outside of town.

View of San Biagio from Montepulciano.

Finished in 1540 by architect Antonio da Sangallo the Elder, it embodies the Renaissance ideals of harmony and balance. Built on a Greek cross plan, it’s central dome rests on a square central base, surrounded by four arms of the church in equal length.

This was the original plan that Bramante had for St. Peter’s Basilica and can also be seen in Rome in the Tempietto on Gianicolo hill. It is no exaggeration to say that when you walk into this architecture it calms you.

Everything is symmetrical and perfect. The purpose? To remind the viewer of God’s perfect universe that you reside in.

Whether or not you believe in the Christian God, this space creates a feeling of sacred harmony.

Day Two

Pienza: The Ideal Renaissance Town

Enea Piccolomini was born in a town called Corsignano but when he grew up to become Pope Pius II he turned his attention back to his hometown with one intention: to transform it into an ideal Renaissance city.

The View from Pienza.

What does that mean exactly? A city made to the measure of man – spacious enough to allow light and air and freedom, but with courtyards and spaces small enough to encourage community. Pienza (literally meaning “City of Pius”) was the new name for this town started in 1459 and it was the first of its kind.

Piazza Pia II: On the left the Palazzo Vescovile. Center: Cathedral. Right: Palazzo Piccolomini.

Remember the church of San Biagio (above)? Harmony, elegance, balance, perfection and beauty. Applied to a city! How could a citizen of such a place not be inspired to do his or her part to maintain an almost divine sense of peace and prosperity within himself, his community, and for his city?

In fact, it’s beautifully maintained to this day and full of flowers. (At the end of the road you can make out an amazing Gelateria: Buon Gusto that offers incredible seasonal flavours!

I also think this cheese shop (La Taverna del Pecorino) is well worth a visit in and of itself! The entire street leading off the main square is chock full of cheese, salumi and wine shops – the perfect place to pick up provisions for a snack (I mean… feast)!

Irresistible

And last of all, it’s where they filmed much of the latest season of the Medici to capture the vibe of Florence at the end of the 15th century.

Bagno Vignoni

Between Pienza and Montalcino (slightly south) you can find this charming little town that still maintains it’s Renaissance-era thermal swimming pool surrounded by centuries old buildings. Even the ancient Romans enjoyed these hot springs and while you can’t take a dip in the central one, you can go slightly south of the town to enjoy the hot spring waters for free or take advantage of the numerous spa treatments and hotels in the town itself.

Photo: DiscoverTuscany.com

Montalcino

Montalcino is famous for its wine: Brunello di Montalcino. Made from 100% Sangiovese grapes, Brunello was the first wine in Italy to be awarded DOCG status (“Denominazione di Origine Controllata and Garantita”) which is the highest categorisation of wine you can get in Italy. Brunello must be aged for at least five years before it is released.

You can also try the excellent Rosso di Montalcino (DOC). Either way, a lunch with a glass of red is practically a must in this town. We stopped at the Taverna del Grappolo Blu where only three cozy tables for two offer this stunning view over the surrounding countryside.

There is a fortress just outside of town to visit and the Main Street is dotted with restaurants and shops.

As main streets of this hill top town wind back and forth on each other so you feel like you’ve gone back in time and as you stroll, you’re rewarded with stunning glimpses over the surrounding countryside.

I enjoyed getting off the Main Street which was just a little too touristy for me (with shops featuring your usual soaps, linens and keychains) and exploring the smaller alleyways of Montalcino.

Where to Stay?

I definitely recommend renting a car to explore this region fully and visit multiple places. The area is full of B&Bs and working farms called “Agriturismi” where you can stay in a cottage or a villa surrounded by vineyards. We tried Borgo del Faggio (found on airbnb, booking.com, Expedia but no longer with their own website) just outside of Montepulciano. Their apartments were perfect for families (full kitchen and access to the pull) and very close to Montepulciano though the interior decor left a little to be desired (anyone else have a problem with bright white lights?).

Have you stayed anywhere wonderful south of Siena? Let us know in the comments below so we can try another place on our next trip!

Ciao from Lauren & Luca!

2 Comments

  1. Sheer torture! Thanks also for the Italian lesson (Pienza). Grazie.

  2. Hi Lauren!
    So wish we could travel right now….I might be more than a little jealous! We were in that area last year in July. We stayed in an awesome agriturismi place near Pienza called Podere Sedalone: https://www.poderespedalone.it/ It was just spectacular, especially the food there. Maybe right up there with Mama’s by the Vatican….memorable…

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