This weekend was full of adventures… the sniff-swirl-swish, stain-your-teeth, and make-all-your-wine-dreams-come-true kind of adventures!

And are there any better kinds?

As you may have seen from other posts, I’m based in the south part of Tuscany for the month of October (if you’re new…welcome, and read about it here). I had been dying to go wine tasting ever since I arrived (trust me…I’ve been tasting, but not in a formal setting). I had a long list of wines and places that I wanted to tick off, and so I set off to tackle “the list.”

First things first..I had to get to Montepulciano from Chiusi. Montepulciano is a small medieval town in the province of Sienna and in the region of southern Tuscany. This town has many wineries represented within the city walls (closed off from the majority of traffic) and within an easy drive. It is a mecca of red wine because of the abundance of Sangiovese grape vines in the area. I hopped on the 7:25 AM bus and arrived to the base of Montepulciano by 8:15 AM. This town is magical…but it is uphill and paved with cobblestones (be weary if you have anyone with you that has any issues with stability). I decided to ditch waiting for the bus that goes directly into the center of town, and face the oh-so-steep walk ahead (my glutes feel like I went skiing…woof!). Since it was quite early, I was in need of a cappuccino and some breakfast. I stopped into one of the most famous spots in the area, Caffe Poliziano and enjoyed the view overlooking the mountains while fueling up for the day and waiting for my ride.

At 10 AM, most of the wineries, cellars, and wine shops open. So at 10 AM, I was ready to roll! We started with tours of the underground wine cellars that are within the city walls. The village has a whole labyrinth of tunnels that connect to each other and hold some of the oldest and best bottles of wine around!

Per my “fave” guy, Rick Steves, I went to meet famous face of Contucci Cantine. So he may not have spoken much English, but he sure can communicate! He is VERY proud that his picture is prominent in Rick Steves’ Tuscany guide, and it is adorable. I would be proud too (#lifegoals)! I had to snag a picture with him myself, as he went on and on about his prized wine varietals.

Next up was Cantina Fattoria della Talosa, where I headed into the earth and scouted out wines from the 1960’s through current day…there’s not much that I wouldn’t do to get my hands on one of those dusty bottles! As we had initially walked up, a couple had been waiting for the winery to open and exclaimed that this place was the best in the city. I’m not sure if this was good timing or strategic marketing, but I was sold! After all, it’s never too early to drink wine in Tuscany (even if it was only 10:15). 

To continue my circle around the center of the city, I moved onto a winery held in an old palace. After all, it’s only the best for these wines! Cantine de’ Ricci opens at 10:30, so I saved it for the last walking stop of the day. The experience was perfect, of course….it’s in a palace! If you are looking for history to surround you while enjoying incredible wines, I suggest you head here without hesitation.

In truth (in keeping consistent with my title of the blog), you wouldn’t need a car to enjoy a full day of wine tasting in the Montepulciano city center. However, if you want to see any vines and get the true experience of the area, you will definitely either want to rent a car (be careful with wine and windy roads) or use a driving service for the duration of your wine tasting. Luckily for me, I had someone who volunteered to drive and loves learning about wine as much as I love drinking it!

By the mid-afternoon, my palette was primed to continue onto my wine pilgrimage throughout the area. We headed off to the Salcheto, which is a modern styled winery with a gorgeous seating area outside with a direct view of the entire town of Montepulciano.  Our sommelier, Clare, was incredibly knowledgeable and made our private tasting a memorable experience, despite that they had a large party arriving within moments. We tasted five wines in total…and may or may not have shipped quite a few home (okay…yes, I did). It was hard to leave…and for certain lucky guests, they won’t have to because there is a bed and breakfast connected to the winery. Talk about sweet dreams!

During the tasting, we witnessed a rare and momentous occasion. It was the annual shareholders and owners harvest celebration, so I got a look into the wine world and all the manpower that it takes to make these bottles a reality. If you have seen “A Year in Burgundy,” you know exactly what I am talking about! Many of these shareholders started chatting up the patrons, and I ended up meeting wine-lovers from all over the world. It. was. heaven.

No matter how fantastic Salcheto was, I had appointments to keep and wines to drink elsewhere. So we headed off for a short stop at Avignonesi. This place is gorgeous! Luckily, they import already to the U.S. and I knew I could reserve my wallet for bottles that could only be shipped home. I strongly suggest someone looking for a special experience to book the lunch and tour at this winery. If you really have some time to spare, check out their fantastic cooking classes. This winery does require reservations for tours, but tastings are held consistently throughout the day without a booking needed.

And swiftly, and after a sip (or 5), we headed towards the land of Brunello: Montalcino. I won’t bore you all with the ins and outs of the legalities of these wines (although, maybe you would enjoy it), but there are strict regulations on what grapes can be used for each categorization, where they are grown, and even regarding the corks! Brunello literally means “little brown” which is due to the color of the wine once it has completed the fermentation process. Due to the regulations, only 100% Sangiovese grapes can be used, making these wines potentially quite pricey.

In riding to Castiglion del Bosco, we past landscapes that words simply cannot due justice. It was one of those moments that speaking was unnecessary, and it would have been sacrilege to not focus strictly on the hills, mountain top towns, red tile roofs, and the sprawling vineyards that seemed to swallow up the road. I was snapped out of my stupor by the need to direct my ride through the town of Montalcino and onto our next destination. This drive was no joke. The description on Tripadvisor actually said that if you think you are getting lost, you are probably on the right track (we did, and we were). We persisted and avoided warning sides of rough terrain along the roadside (it is an UNESCO World Heritage Site, so they are not allowed to pave the road), and drove up to the 5 star hotel of Rosewood Castiglion del Bosco. The son of Salvatore Ferragamo owns the hotel/winery, and the details truly reflect the feeling of a monumental fashion influencer.

After an incredibly hospital welcome to the hotel lobby, we realized that we were in the wrong place…but not by much. We gulped down our “welcome” espresso’s and headed 200 meters away to the “cantina.” When I say cantina….I mean huge facility where all wine dreams come true. The processes here are completely sustainable, and they have even used their previous wood barrels to cover the walls of the hallways. They refer to their aging room as “the church” because of the arches (and because it is practically Biblical how wonderful everything is here.)

Once again, our sommelier was extremely knowledgeable, welcoming, and persistently the perfect hostess. Before our tasting, we were given once last surprise: a visit to the wine library. The lockers in this wine library are $8000 (for a full lifetime) and filled with $2500 worth of wine upon purchase (which could actually be just one bottle of their most prestigious Zodiac line wines that are aged in barrels of 400 year old oak). We tasted 6 wines, and one of which was from one of the best years that the vines have ever yielded. This was the perfect way to end the day. We wrapped up our tasting and I splurged on one of their more “realistic” bottles to take home with me.

I’m not sure if it was the wine’s influence, or just how happy I was for such a magical day, but as we drove off I teared up for a moment…but now I’m just embarrassing myself.

I didn’t get a chance to visit all that I wanted to (after all, I was touching the tip of the wine iceberg. However, the silver lining is that this just gives me a reason to come back!

Did I miss anything? If you have tips for readers regarding this area, please share! After all…I’ll need them for my return visit!