Our friends are getting married in Italy! We found out this news and we couldn’t be more thrilled. But we told them right away there was no way we could possibly make it. I am a teacher and I never take days off in October. It is the beginning of the year, students are just settling in, and teachers get so many days off in the fall. We told them we were over the moon for them but they didn’t have to invite us because we couldn’t pull it off. Well…. We got invited and let’s be real we couldn’t turn it down! Will we ever go to another wedding in ITALY? A girl can dream.
The man who ran the catering for the wedding we attended was poking fun at us and saying that American’s always say “oh my god, AWESOME, amazing, WOW”. But honestly, those are the words to describe almost everything you see and do in Tuscany!
So here are all the details about spending 4 fast and furious days in Tuscany Italy. Our 4 days included a wedding so I will also add in some of the things that I would have done had we not spent 1.5 days at the Villa (the AMAZING villa).
Day 1: Montepulciano
We flew out of Philly on Wednesday evening to land in Rome early Morning Thursday. Click here for my post on how to utilize your time for travel. We flew into Rome because it was a direct flight and cheaper from Philadelphia. Florence would have also been a great option, as the wedding was in the hills of Tuscany about 45 mins outside Florence.
We had a rental car booked for our arrival in Rome. We picked up the car and drove 2.5 hours to Montepulciano. We made a quick stop at a road side gas station for some crudo and espresso, nothing better! We arrived in Montepulciano and checked into our amazing bed and breakfast Residenza Fabroni. Upon check in they suggested a place for lunch “La Dolce Vita”. The recommendation was PERFECT. We got some charcuterie, pasta of course, some wine and enjoyed a delicious lunch. We spent the afternoon exploring the town, popping in and out of wine shops, doing wine tastings and exploring cellars. We then returned to our accommodation for the best part of the day. Our hotel had a wine and local product tasting on the roof. This tasting went on for at least 2 hours and we tried 4 full glasses of wines and a Prosecco. Throughout the course of the tasting, we had charcuterie, cheese, tuna, stuffed peppers, veggies, sandwiches, and the list goes on. Everything we tasted from wine to food was made and produced locally. The experience was magical and I could not recommend it more highly.
Gas station crudo.. chefs kiss! 
View from the tower in the main square 
breakfast at Cafe Poliziano 
Rooftop wine tasting at Residenza Fabroni 
Amazing experience at Residenza Fabroni 
View from the suite at Residenza Fabroni 
Wine tasting 
Ducking into wine shops for tastings 
Charcuterie at La Dolce Vita 
Blue room at Residenza Fabroni 
View over the countryside 
Walking into the town square 
View from the rooftop of Residenza Fabroni 
Ready for our big day
Day 2: Tenuta Monaciano
The next morning our accommodation gave us vouchers to have breakfast at “Cafe Poliziano” which is one of the most popular cafes in town. The view from the Café out into the surrounding countryside looks like a painting. I had a chocolate croissant that was like nothing I have ever had before; it was just oozing chocolate. We then explored the town, went to the top of the tower in the town square (which is quite an interesting experience) and made sure to see the last of all of the sights before heading out to Siena to the wedding venue. Overall, our day in Montepulciano was a dream day that I will remember forever and I can only hope to return one day!
After leaving Montepulciano we had a 45-minute drive to the wedding venue. We decided we didn’t want to arrive at the venue hungry, so we found a road side restaurant to have lunch. We used google maps to search for a place along our route and we got VERY lucky. We found “Antica Trattoria Botteganova” and it was a wonderful late lunch stop. We shared a charcuterie and a few pasta dishes and a bottle of wine and we were all very pleased with everything. Then we continued on to the wedding venue for an evening of wood fired pizza and seeing all of the other guests!
Day 3: Siena/Monaciano
Day 3 was wedding day, but we woke up early because we still wanted to explore. We drove 10 minutes into the town of Siena. Siena is a captivating town with a very special large square. The square is home to a horse race once a year. It is hard to imagine what this would actually be like, and definitely worth a google. We explored the town and the square and also went inside the Siena Cathedral. It was truly one of the most impressive cathedrals we have ever seen. We were also unknowingly lucky enough to see the floors which are covered up for most of the year. Good timing for us! We had really been hoping to eat at the restaurant “Taverna di San Guiseppe”. We showed up right when they opened and asked to be seated for lunch and we got in! This is a Michelin guide restaurant and in my experience that can be hit or miss. This was a HIT. The staff were incredible, they were so kind and thoughtful. We mostly ordered pastas because we were Americans in Italy after all. I had the lasagna and it was incredible. We were so thankful they were able to fit us in and I would highly recommend a lunch or dinner here.
After our morning in Siena we returned to the wedding venue for the Italian wedding of dreams!
Pizza Party at Tenuta Monaciano 
Pics with the Cathedral in Siena 
The Siena Cathedral 
The square of Siena, very lively on a Sunday 
Streets of Siena 
Enjoying the wedding! 
The beautiful ceremony location at Tenuta Monaciano 
Lasagne at La Taverna di San Giuseppe 
Glimpse into the Cathedral 
Views of the countryside
Day 4: San Gimignano & Siena
On day four we woke up bright and early to visit the town of San Gimingnano. It was a good thing we did, this small town is very popular and parking was filling up already as we arrived (at least at the parking area nearest to the town). We absolutely loved strolling the streets here and seeing the towers of San Gimingnano above the town. Long ago the nobility of the town-built towers as a show of wealth, status, and power. At one time the town was full of towers built by different families. Now 14 towers remain in the town and you can also climb to the top of one of them for amazing views over the town and surrounding countryside. This town was also appealing to us because it claims to have the “Best Gelato in the World” at a place called “Gelateria Dondoli”. We tried this gelato and really enjoyed it, however, we think we found the best gelato in the world… and it was just across the square at a place called “Caffetteria Gelateria dell’Olmo”. Either way you can NOT go wrong and both places were incredible. I highly recommend sampling both during your time in San Gimignano. The best part of San Gimignano and one of the absolute best parts of our trip was lunch at “Ristorante Peruca”. I had seen and read about this place prior to coming to Italy and had high, high hopes. My hopes were met and exceed. I went specifically to try one dish on their menu that I had read about in another blog post and it was everything I dreamed it would be and more! We tried almost every pasta on the menu between our group and every single thing was incredible. I would go back to Tuscany just to go back and eat at this place. It was a wonderful hidden gem and I am so thankful that we went. The service was also so kind, pleasant and welcoming and the white Vernaccia wine was the perfect accompaniment to the meal.
In the afternoon we returned to Siena to meet up with our friends from the wedding and explore the town some more.
The “real” best gelato at Gelateria dell”Olmo 
Views of the towers 
The Farmers Bundles: pasta filled with pecorino cheese and pears, San Gimignano saffron sauce with pecorino cheese and pine nuts 
Peruca risotto: with cinta senese ham, zucchini and truffle 
Spotlight on Gelato 
Gelateria Dondoli 
Sunday in San Gimignano 
View from the top of the tower 
More tower views 
Beautiful town square
Suggestions if you have more time
As you can see, if we did not attend a wedding there would have been some more free time in our schedule. Here are some suggestions for what else we could have done within those four days.
Florence
Florence in itself could be a four-day trip. But if you are in Tuscany, it is an amazing stop with a list a mile long of things to do. It would also make an excellent base for traveling the area to all of the smaller towns, and requires a whole blog post in itself.
I also have a post about things in Florence that I found to be worth the hype, you can check it out here —-> 6 Things in Florence, Italy that were worth the hype
Montepulciano (a second day)
I would have spent a second day in Montepulciano to explore the vineyards all around the town. There are vineyards and wineries right on the outskirts of the town and you could join an organized tour or just explore them on your own with a full day.
If you’re looking for more information about Montepulciano you can check out my post here —–> 24 hours in Montepulciano, Italy
Lucca
This town is adorable, walkable, and small enough to do in a day or a half day. I recently had the chance to visit and added it to my list of day trips from Florence.
If you’re interested, you can check that post out here —-> 5 day Trips from Florence
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