A Day in Tuscany With Viator...AKA The Day We Drank All The Wine

Ahhh Tuscany. Think rolling green hills, brilliant blue skies and adorable towns standing high on hilltops throughout southern Tuscany. The Val d’Orcia region is protected as a UNESCO World Heritage site, and is quintessential Tuscany -- gorgeous landscapes, vibrant hill towns, Renaissance architecture, charming (and steep) streets, and of course, some of the best wine in the world (but we might be biased).

Views from Pienza

Staying in Tuscany is always the best option, but if you’re a part-time traveler with limited time off like we are, day trips are the way the way to experience the best of both worlds. During our whirlwind Italy trip in May, we stayed in Florence 3 nights and booked a day trip to Montepulciano, Pienza, and Montalcino through Viator.

Montepulciano and Church of St. Biagio

The more popular day trip from Florence includes stops in Siena, San Gimignano, lunch at a Chianti vineyard, and Pisa, but wine drove our decision to opt for the Val d’Orcia tour.  Brunello di Montalcino and Nobile Montepulciano wines are some of the best reds in the world.  Solid go-to Italian wines if you ever find yourself staring at a wine list not knowing where to begin.


For our Day in Tuscany trip, our tour had pick-ups in both Florence (train station) and in Siena. While booking, we could select to meet at the train station, or have a free pick up at our Airbnb. We opted for the free pick up, but for drop off it will cost you extra.

You visit a winery for tastings, Montalcino, Pienza, and Montepulciano, where you can tour a wine store and cave and get a second free tasting. Unlike the more popular Tuscan Day Trip from Florence, food is not included on this tour, except some crackers/cheese/meat and assorted appetizers at the two tastings, so beware of wine tasting on an empty stomach (unless you’re into that. You cheap date, you.)


The first stop was in Montalcino at the Abbadia Ardenga winery. The property spans over 1600 acres, and has a long history of winemaking. It was previously owned by the family of Pope Pius II, who was also key to the development of the town of Pienza (next stop on the tour). The vineyards on the property are solely dedicated to growing the Sangiovese grape varietal and produces 40,000 bottles of wine annually.

For the tour, we had a brief introduction and history lesson from the owner, an adorable older gentleman (who really has a thing for the ladies - you’ve been warned ;)) named Mario. Mario speaks no English, but was there for our entire tour, from learning about the property and family, to pouring wines during the tasting.

We tried four wines - a Rosso di Montalcino, two Brunello di Montalcinos (a D.O.C and D.O.C.G) and a white wine - Vinsanto.  We also opted to try the Brunello di Montalcino Riserva - the best of the best - which Mario will open if you’re interested in purchasing.

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Enjoying Tuscan wine!

Four tastings may not sound like much, but when you skip breakfast, it does the job.  After the tastings, the buying of ALL the wine, and a few pictures with Mario, we were off to the town of Montalcino.

Helloooo Mario
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We had about an hour to spend wandering the hill town of Montalcino.  It was super charming with lots of shops and a fortress for a great viewpoint (Fortezza di Montalcino).  Fresh off the wine tasting, we grabbed a group of newfound friends from the tour and stepped into another wine store that offered a tasting. Our motto -- when in Tuscany….drink all the wine. After buying even more wine (we have a problem), we had just enough time to grab a quick cappuccino (what else goes better with copious amounts of wine) and head back to the bus.

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The next stop was Pienza  - the cutest little town and the home of Pecorino cheese. Wine, wine, coffee, more wine..and now cheese.  We. Were. In. Heaven.

It was the smallest town we visited, but had an adorable town square with a flower field and beautiful church. The views were amazing and not to be missed.  After a few photo ops, we once again found our new tour friends and went cheese hunting.  

All throughout town there are little storefronts with cheeses, meats, and more wine.  We hit about 4 different ones that offered cheese plates and all shared.  We also picked up some cheese, salami, and some truffle glaze with balsamic vinegar to go for our trek to Cinque Terre the next day at a storefront called La Taverna del Pecorino. The store employee (shop owner? Not sure) was the BEST. He let us try tons of different meats and cheeses and the various flavors of balsamic glaze, so definitely stop in there if you ever find yourself in Pienza!

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Chris here -- This was by far the stop I was looking forward to most of all. For many years, wine from Montepulciano has been my go to when staring at a wine list not knowing where to begin (note -- Vino Nobile is different from Montepulciano d'Abruzzo). Generally affordable, but solid, easy to drink, and goes along with most meals - well, at leasts to my unpolished palate.  I had also heard great things about the town itself, so this tour through Val d'Orcia shot the top of my list.

Unlike many wineries throughout Tuscany that require transportation in between tastings, the town of Montepulciano offers walkable unique cantina tastings among its historic streets. On the tour, you had an option to wander on your own for about an hour and a half, or get a cellar tour in the former dungeons turned wine cellars of Azienda Agricola Ercolani, which ended with some light appetizers and free tasting.  Because, well, dungeons and free wine, we opted for the tour.

They offer the tour and free tasting whether or not you're on a larger tour, so if you find yourself in the area, make sure to stop in. Some other popular spots in town include the caves of Cantina Fattoria della Talosa or Contucci Cellars, or the modern Cantina Salcheto with an incredible view of Tuscany’s rolling hills.

After the tour we had about 45 minutes to wander. We stopped in some shops, then made one last quick stop for more wine and to soak up those Tuscan countryside views at Caffe Poliziano. Do stop in and snag a coveted terrace seat and enjoy some wine - or coffee - and GORGEOUS views!

Enjoying Vino Nobile di Montepulciano and espresso on the terrace at Caffe Poliziano


We booked a few tours through Viator for this trip and found it to be a pretty easy process.  They contract with smaller tour groups, so you’re still supporting local tour guides, but we found the many tour company options to be somewhat overwhelming.  We had great experiences on all of the Viator-booked tours, with fantastic tour guides. Cin Cin!

Tour information is here, and our cost was about $72 per person.

If you're new to Viator, use this link to get $10 off a tour.

Full Disclosure -- if you book and complete a trip, we'll also get $10 towards a future tour. Also note -- this is not a sponsored post. We paid for this tour and views are completely our own.