There’s a top-secret, teeny-tiny town tucked into the hills of Tuscany: Montalcino.

Population? 5000.

Views? Try the highest hilltop in Tuscany.

Vineyards? Also about 5000.

Montalcino is on our radar because we dig its low-key, no-other-tour-groups-are-here vibes.

That’s why we stay there for two nights on our Greatest Hits tour –– and we pick our spots very, very carefully.

So, why is Montalcino super special?

Three reasons:

Reason #1: All. The. Wine.

Montalcino might be ringing a bell for you because you’ve likely poured a glass of Brunello di Montalcino before –– it’s one of the most famous red wines in the world, and when you visit, you’re smack-dab in the middle of all the goodness that makes it so.

Because Montalcino is perched high up in the Tuscan hills, it’s basically the *perfect* place to cultivate the kind of wine that makes you wanna ditch that extra pair of shoes you packed so you can fit a few bottles into your suitcase. It’s drenched in the kind of sun exposure that grapes adore.

What makes wine in Montalcino specifically spectacular is that it’s made with a Tuscan type of grape from the Sangiovese vine, called Brunello. Brunello is known for producing wine with a bold and fruity flavor, high tannin (that’s what makes wine taste “dry”) and high acidity.

Want a unique winery experience in Montalcino?

Get off the beaten track (seriously, download your Google Maps to use it offline to get here) and take the windy drive to Azienda Agricola Uccelliera, a vineyard free of crowds and full of pleasure. This unsuspecting family-owned winery is tucked away in Montalcino and produces some of the best vino around –– they’re frequently recognized as one of the top Brunello producers every year. You’ll get to try some wine straight out of the barrel at different stages of ageing (so incredible) and fall hard for their top-notch olive oil. Be prepared to wanna ship all of it back home.

montalcino tuscan hills and cypress trees

montalcino wine

Reason #2: Va-va-voom Val D’Orcia.

This UNESCO Heritage Site is right in the middle of all the wine-rich Tuscan towns: Siena, Montepulciano, Montalcino. (There’s no better view than Montalcino though, being at the tippy-top of the hills here.)

This is the landscape that inspires paintings featuring quintessential rolling hills, cypress-dotted countrysides, old olive groves, cool castles, churches, chestnut trees and tall towers. It’s rural Tuscany that looks like it hasn’t changed in centuries (barring bunches of wildflowers now), and that’s precisely the point.

Dreamed of Vespa-ing through vineyards through Tuscany before? There’s no better place to do it. Montalcino is one of the best spots to hunker down and explore the Val D’Orcia from. When we travel here on our Greatest Hits tour, we’ve handpicked the perfect hotel overlooking this sprawling landscape so that we’re enjoying it wherever we are (read: poolside sipping some Brunello or cruising through the countryside with our private drivers).

Want a unique experience in the Val D’Orcia?

Visit Bagno Vignoni, the Tuscan town that swapped a central square for… a giant tub. Dipping into the 49°C thermal waters here has been a ritual for locals and visitors alike since the 16th century — Christian pilgrimages to Rome used to make a regular stop here back in the day. Frequented by Popes and other Roman celebrities, they all adored these baths for their apparent healing powers.

Kick your experience up a notch and spend a day at a private spa here like Le Terme.

For getting around this area, you’ll absolutely need a car (or a Vespa!) — which can be rented in Chiusi/Chianciano Terme if you travel from Florence via train.

montalcino fortress

montalcino vineyard

Reason #3: Medieval mystery.

Montalcino looks like it’s barely changed since medieval times –– there’s more cracked cobblestone than there are shiny storefronts here. The town’s history can be dated back to the Roman and Etruscan periods, and came under Sienese rule in the 12th century. We love that you can still see the fortress built to defend the town against Siena and that we don’t totally know how many rulers it *really* came under…

But what we do know is that it’s a total trip back through the ages to stay and play in this spot. Meandering mazes of skinny streets, chipped churches, oh-so-ancient villas and drinking wine that traces its production methods back a couple centuries = pretty groovy experience.

Want a unique *medieval* experience in Montalcino?

You gotta drink wine in the cellars of the famous fortress perched at the top of the town, Enoteca la Fortezza di Montalcino. You’ll get to explore the hidden cellars, receive a customized tasting of vintage Brunellos based on what you love, snack on antipasti along the way and do as the ol’ Tuscans did.

Plus you’ll get to head home saying: “I drank wine in a medieval fortress in Tuscany.”

montalcino street wall

montalcino tower and sunrise

A perfect day in Montalcino with Italian Fix

We spend two nights in Montalcino on our Greatest Hits tour, and here’s a sneak peek of what one of our days sampling the best of this gorgeous town looks like.

Like all Italian Fix tours, our philosophy is “it’s your vacation — do what you want!” You travel with a bilingual guide and a private driver.  Every day we have an itinerary that balances busy with downtime. You can join in on the activities or do an alternative.

For example, our guests who want to be out getting some exercise can enjoy a historical walking tour that winds through the streets and alleys of Montalcino, and sets you up to see some of the greatest vantage points from the city walls overlooking the valleys.

Guests who prefer to have some fun in the kitchen can join a cooking class that focuses on traditional Tuscan recipes they can recreate at home. Afternoons spent with mammas in the kitchen are always so much fun!

We love the flexibility and so do our clients! Do what makes you happy that day.

In Montalcino we stay at a small, family-run hotel overlooking the sprawling Val D’Orcia — sip your espresso in the spring air that’s already nice and warm.

In the afternoon, we have some downtime. Finish that book you bought on vacay, chat with your new friends about the day (or the last city we just came from: Rome!) and pinch yourself as your eyes are treated to the best views of the countryside beneath you.

After some dolce far niente, we all head out for the evening just as the sky takes on that Tuscan terracotta glow at sunset. We whisk you away to visit two special vineyards (including one where they serenade their vines with classical music) and finish off the night at a secret restaurant tucked away into the countryside.

You slip into soft sheets back at the hotel feeling like a Brunello expert, Tuscan chef and all-around-new human thanks to surrounding yourself with the best company for the last three days. And tomorrow, you’ll be in Florence.

montalcino abbey

montalcino vineyard


Wanna travel to Montalcino with us?

Join us in April 2020 on the tour we call Greatest Hits, where you’ll see, do and eat it all in Italy’s iconic hot spots.

Rome, Montalcino, Florence, Cinque Terre, Lake Como and Venice.

We’ve only got one date available in 2020 for this 12-night experience:

==> April 25 – May 7 (all adults welcome).

Click here to snag your lounger at our poolside.

Got questions?

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