A Weekend Under the Tuscan Sun

A weekend under the Tuscan Sun in September is a DREAM! This was our second trip to Tuscany during that month and the weather was just perfection. Cool air, hot sun, wineries upon wineries, rolling hills, the pool, the amazing food…like I said, so dreamy.

We went with our friends who also have three boys, and it was SO much fun! We found the most beautiful and amazing Italian Villa and rented it out for four days for all ten of us, and it could not have been a more perfect experience! It had the most unreal views, a giant outdoor terrace overlooking the rolling hills, the biggest pool Ive ever seen (& it was all ours!), and was able to provide us with a private chef on our last night! More on that later! Ive linked the home, and I highly recommend this place if you’re visiting Tuscany. We kept looking around all weekend saying “How is this real?” It was so incredible. 

Day 1

We woke up and enjoyed our coffee down by the pool while the boys swam, it was so lovely. WE had prescheduled a lunch and wine tasting at Castello Albola, so headed there around lunchtime. I never want to be negative, but to be honest, our experience here was not so great. There were some misunderstandings, so we ended up waiting almost two hours to even start lunch, and with six boys that were starving, it was a bit tricky. 

Now the food, it was AMAZING. Every single thing we ate, we all loved, and we tried everything on the tasting menu, it was fabulous! The wine was good, though another issue was them trying to swindle a bunch of Americans into buying a vintage that they had an overstock of because it was a bad year…kind of left a bad taste in our mouths to be honest. My husband had done his research before going here, so on our way out he bought one bottle of the year he knew was highly rated. We ended up opening and trying it that night and loving it, so we went back to buy a case of that, so that was good at least. Ha It really was beautiful though, and the boys got to run around under the olive trees while we enjoyed each others company, so I can’t complain too much!

When we left there, we headed 10 minutes up the road to a very small family run winery called Barlettaio. On our way in, our friends youngest tripped and hit his head on a rock. Poor guy needed a few stitches, so we kept their other two boys while they took him to the hospital. We stayed for about an hour trying their wines and letting the boys play, and Im so glad we did. The wine was amazing and the views were beautiful.

Since part of our party was missing, we headed out, took the five boys to a playground and for gelato, while we sat at the cafe with drinks and snacks. We picked up some fresh pasta before heading back to the house and made a delicious dinner while we all hung out and listened to music. We typically don’t cook when were on vacation, but it was actually so fun blasting music, dancing around the kitchen, and sharing a bottle of wine with my husband. We loved that evening!

Day 2

We woke up and headed straight down towards Montepulciano! We stopped just outside the town at Canneto for a wine tasting and it was amazing. Again, the views were incredible and the wine was fabulous. We spent a couple hours here soaking it all in and just enjoying our company before heading to lunch a few minutes down the road.

We went to Tre Stelle and It was perfect for families, outdoor tables, swingsetset and play area fo the kids. We loved our food and found a good wine  on the menu as well!

We drove through this gorgeous road lined with Cyprus trees on the way to lunch, so naturally we had to stop for a little photoshoot! Lunch was delicious, and had a playground for the boys so it was a perfect spot before heading into Montepulciano for the afternoon!

Once in town, there are little wineries throughout too, so we hit up a few of those. We loved Contucci Winery. Go to Talosa winery and walk down the stairs to the coolest wine cellar. Try some more wines at Perbacco Wine Experience, which has a large variety of wines. End your day around the corner, tasting at Crociani Winery. Their Reserva is fantastic, and don’t miss their olive oil. So good. 

 If you’re a Twilight fan, like moi, then you know Montepulciano is home of one of the famous scenes. The on in New Moon, where Bella runs across the square tons top Edward from revealing himself in the sun to everyone! Ha So naturally I had to get a picture there while all the b boys were enjoying some gelato!

From here we were starting to think about dinner, but hadn’t made reservations anywhere, and since its such a small town, everywhere was booked and coudnt fit ten of us. We headed out and started driving back to our Villa, which was about an hour away. We ended up stopping in Montevarchi at Da Giorgio for dinner and it was a perfect little local spot to end our day. 

Day 3

We headed into a really cool little town called Radda, that was only about 20 minutes away. We grabbed pastries and coffee and watched street musicians playing. We walked through town and did some shopping, then, you guessed it, tasted more wine! Ha! We stopped in at Enoteca Toscana, and he had so many amazing wines. We tasted a good variety, and all walked out of there with a few cases. 

At this point, we had promised all the boys a day at the pool. I mean, we had this gigantic pool with amazing views, so it would be a shame to waste it! We grabbed all the making of a good charcuterie board and headed back to the house around lunchtime to relax, eat, swim, and drink some more wine! It was such a lovely and relaxing afternoon. 

That night, we had arranged for someone to come to the house and cook dinner for us. It was a highlight and something you shouldn’t skip! They went all out with an Antipasti, Primi, Secondi, and Dolce. Every course was fabulous. The panna cotta was easily the best Ive ever tried. We loved it so much my boys begged to recreate it for family when they came to visit, and we did!I wish I had more pictures of the food, but I was so just enjoying every of this experience. When I tell you it was one of my favorite moments we’ve had in Italy, Im not exaggerating. The terrace with the long table, the sunset, the views, the food, the wine, the company..it all rolled into a perfect memory that Ill just never forget, and never get over that it was real. We kept saying “what is this life!” Truly such a magical experience and a perfect end to a weekend under the Tuscan Sun!

We headed home the next day dreaming of every moment!

**If you want to see some of this in action, I have a whole two story highlights on my Instagram titled Tuscany 2021. 🙂

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