Your Tuscany Italy itinerary isn’t complete without unforgettable experiences like Montepulciano villas, wine tasting, cooking classes, truffle hunting, and e-biking adventures.
In our 4 day itinerary in Tuscany, We started the morning at our beautiful hotel in Florence with a short walk to Rooster Café — and honestly, I’m mad I didn’t discover it sooner. Tiny place, maybe four tables and a bar, but worth every minute of the 30+ minute wait. Rooster, if you’re reading this… I miss you already.
After breakfast, we booked it back to the hotel, grabbed our luggage, and headed to Avis Car Rental, where I had this fantasy that we’d grab our keys and be cruising the Tuscan hills in minutes. Cute, but no. Turns out every single tourist in Italy had the same plan that morning. The place looked like the DMV… and even had a pull a number to get in line.
We found a sliver of floor to stand on, and waited our turn. Eventually, someone handed us keys to a car. The Avis employee gave us an upgrade to a sporty Alfa Romeo. My husband came armed and ready with his international driver’s license, but all they wanted was his NC license.
Our destination was Montepulciano (the name feels like drinking red wine in slow motion.) The drive was a smooth 1 hour 40 minutes, with a quick pit stop at a highway gas station that gave serious Tuscan Sheetz vibes. We stocked up on ice cream sandwiches and chips and drinks.
Lunch was at Ai 4 Venti, a charming spot right in Montepulciano’s historic center. Everything was fresh, homemade, and paired with wine.
Then we arrived at La Vittoria10, our dreamy villa for the next 4 days. It was everything: olive trees, stone walls, rolling hills, and Fulvia — the warmest, most welcoming villa host in all of Italy. She hugged us like we were long-lost family and gave us a grand tour while our kids whispered, “Can we just stay here the rest of the trip?”
We did a quick grocery store run (which took 3x longer than necessary because Italian grocery aisles are a scavenger hunt), and then Fulvia sent us off to dinner at Dopolavoro La Foce. This meal was DELISH. Gorgeous views, perfect food, and we ordered every dessert on the menu. Every last bit was devoured.
Between this and La Bruschetta back in Florence, we definitely reached peak Italian dining.
Tuscany Italy itinerary
Day 2: Wine Day — Villa Sant’Anna Style
Villa breakfast was laid back: yogurt, cereal, coffee — just enough to prep us for a very important wine tasting.
Fulvia booked us a private tour at Villa Sant’Anna, a small, family-owned winery in Montepulciano that was gorgeous. Similar tour HERE. And we were the only ones there. They were filming video for marketing purposes that particular day – while we were on the wine tour and swirling wine during the tasting – we may see ourselves in some cool Sant’Anna commercial in the near future.
Simona, the owner, was an absolute gem — smart, kind, and pouring wine like it was her superpower. She walked us through the wine-making process, shared her family’s legacy, and kept our glasses happily full while we snacked on lunch. She even gave us a crash course in how to properly hold, swirl, sniff, and sip a glass of wine — which basically confirmed that we’ve been doing it wrong our whole lives. Honored (and slightly buzzed) to be learning from the best in Italy’s wine country!
And when I say the wine was good, I mean we bought more than we could carry and arranged to have it shipped home…, once the Italian and American summer heat chills out. The wait was painful, but worth it. My favorite wine HERE.
Back at the villa: hot tub + wine = perfection.
Dinner was arranged by Fulvia (again, love her!). We went to Ristorante La Casina, where the plan was to pace ourselves, but we inhaled focaccia and devoured Pappa al Pomodoro.
Day 3: Truffle Hunting & Italian Chef
Another peaceful breakfast at the villa before our next adventure: truffle hunting.
Our truffle hunter showed up with two energetic dogs, and we followed him in our car to a secret spot in the woods.
He and the dogs did all the work while we just stood there applauding. They’d dig, find truffles, and plop them at our feet like little treasure hunters. The dogs deserved Michelin stars and steak dinners, honestly.
Pro tip: While in the area, try to visit La Foce Gardens. It’s 5 minutes from the villa and supposedly stunning. We tried… but they were hosting a private event and we couldn’t get in, which made me want to see them even more.
So instead, we went to Bagno Vignoni, a thermal village that looks straight out of a Renaissance painting. Ancient Roman baths, cute shops, and gelato at the end of lunch at La Terrazza Bistro.
Back at the villa, we have a pasta-making class with Chef Asia.
She rolled in, set up, and within minutes we were elbow-deep in flour and forming fettuccine, ravioli, and spaghetti like professionals. Dinner included everything we made, plus Sant’Anna wine and Chef Asia’s tiramisu to seal the deal.
We had the best time at the villa that night.
Day 4: E-Biking Through Tuscany (a.k.a. My Quads Still Hurt)
Another morning, another peaceful breakfast at the villa — coffee, pastries, and the internal pep talk of a lifetime, because today… we were going e-biking through Tuscany.
Right on time, Andre (our biking guru) rolled up in a very sleek van fully stocked with bikes, helmets, backpacks, waters —we were ready. He even brought extra bikes just to make sure the kids had the perfect fit. Total respect.
Now, I’m not exactly sure how far we biked — somewhere between 10 and 1,000 miles — but I can tell you this: e-bikes are not easy on dirt. They help, yes. But they do not turn gravel hills into smooth, breezy roads. We spent most of the ride gripping our handlebars like we were holding on for dear life, dodging rogue pebbles and hoping our brakes were up for the challenge – and workout!
The views. . .were just like the movies. Rolling hills, sunflowers, vineyards.
Our final destination was Pienza, a town so charming, it did not feel real. We had lunch, gelato, and walked the streets.
By 3 PM, our legs were nearly numb. Andre kindly loaded up the bikes, drove us back, and we collapsed in the villa.
We have so much respect for this region in Italy! All the adventures planned by the amazing Fulvia made things so much easier! Reach out to her and you will be treated like VIP in Tuscany!
Drop me a line if you are planning to go to Tuscany. I would love to hear from you.
