Best of...

Guide to Montalcino

A medieval city-on-a-hill, Montalcino affords astonishing scenery and a glimpse into a region relatively unchanged for the past 500 years. It also offers unparalleled varietals for wine enthusiasts. As home to the illustrious Brunello wine, Montalcino can safely be described as an oenophile’s dream. The town’s narrow, steep streets and medieval walls that encircle the center contribute to the authenticity and charm of the region.


In addition to its wealth of wine options, Montalcino also houses several wonderful eateries. During the day, the main square’s Caffe Fiaschetteria Italiana (Piazza del Popolo, 6; (39) 0577-849043) is a great spot for lunch, coffee or a snack and to soak up the venue’s history. Founded in 1888 by Ferruccio Biondi Santi, the father of Brunello, Caffe Fiaschetteria is as integral to the wine’s backstory as the vineyards themselves. Another equally enticing lunch option is Osteria Osticcio, whose light dining options compliment their wine and the magnificent terrace view.


Enoteca La Fortezza

, a cavernous wine shop at the city’s highest point, offers tastings and sells Brunello vintages. The climb up to the fortress tower provides a stunning view all the way to Montepulciano. Shipping wines home from the Enoteca is pricey but reliable.

See & Do

In the mecca of wine country, Ciacci Piccolomini d’Aragona (Loc. Molinello; (39) 0577-835616) and Casanova di Neri (Podere Fiesole; (39) 0577-834455), both family-run wineries, have a more intimate feel and provide a good understanding of the region’s favorite libations.

Castiglion del Bosco offers cooking classes that allow guests to prepare and taste some of Italy’s most traditional and delicious recipes. Ingredients are selected from Castiglion’s organic kitchen garden and then chopped, sautéed and heated to perfection. Sant’Antimo Abbey, a 12th-century monastery 35 minutes by car from Castiglion del Bosco, is home to monks clothed in traditional attire who sing Gregorian chants.

Published onAugust 20, 2015

More Inspiration

Plan Your Trip With Us

We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities.

Get In Touch
Indagare employees walking up stiars

Enjoy 30 Days On Us!

Start your Self Planner
membership trial today.

Unlock access to 2,000+ first-hand hotel reviews, 300+ Destination Guides and the most up-to-date travel news and inspiration.

Already a member?

Welcome back,
log in to Indagare

Not a member?

Forgot Password

Enter your email and we’ll send you a link to reset your password.

Type the first 3 letters to begin