Italian Adventure Part 4: Full day tour of Siena & San Gimignano…

When I was booking this trip I decided rather than stay in Siena (which was my original plan) I would stay in Florence and use it as a base camp to explore the region. That way you are not lugging your bags all around the train station consistently (which I HATE). I tell my clients this all the time. So, I decided to book a small group VIP tour with one of my favorite tour companies in Italy, Florencetown Tours. They are AMAZING. I have taken several tours with them, and I highly recommend them. I wanted to do something different. I wanted to do an off time. I wanted a unique experience. I didn’t want to be in Siena with the busloads full of tourists. Florencetown had an incredible afternoon small group tour, with dinner in Chianti. I was sold. They are such an excellent and attentive company that any journey you take with them will be phenomenal. Our first stop on our VIP small group tour was Siena.

Siena was once the wealthiest town in Europe. Before the plague. It’s really where modern-day banking began. Siena’s is made up of 17 Contrada (neighborhood) each with their own distinctive vibe, leading to the main square the Piazza Del Campo. The Campo is a fantastic public spot. Tons of eateries and snack shops (get the lemon cookies. They are AMAZING). Siena is a great city just to get lost. Walking around and exploring it on your own. Make sure you visit the famous Duomo. One of the most beautiful cathedrals in all of Europe. With a mix of Italian Gothic, Romanesque, and Classical architecture, it a pretty breathtaking view. City Hall is also an impressive site. It’s been the city hall for Siena for over 600 years. The courtyard is free to visit and walk around. A must see.

Piazza Del Campo

The Duomo

If you want to see something truly spectacular, make sure you are here during the Palio Di Siena. It happens only twice a year July 2nd and August 16th. This world-famous event is when 10 of the 17 Contradas race for about a minute and a half around the Piazza for bragging rights. Well, a bit more than bragging rights. Winning is a source of great pride for the neighborhood that wins. There is no money but, only the glory in winning. Getting tickets can be taxing. If you are interested in getting tickets make, sure you book early and be prepared to pay. They can get as high as 5000 euros for a good seat. Many packages include tours and dinner as well.

After stuffing my face with an entire box of cookies (seriously, those cookies were incredible), we were off to see San Gimignano. One of the more famous of the Tuscany hill towns.

Upon arriving you can immediately tell this was a mid-evil city. The entrance is a vast massive gate. Surrounded by the rolling hills of Tuscany.

We had a bit of free time on our own here, and I wanted one thing. WINE… And cheese… and meats. Mostly wine though. The city its self isn’t significantly large. The narrow streets are filled with shops, cafes, and eateries. Just what I was looking for. I wanted to park it, get a bottle of wine and people watch. After a bit of R and R, I was ready for some shopping. Now, I was on a mission here. I had brought a whole other bag just for treats. I was prepared for all things wine, cheese, cured meats and oil related.

After spending WAY too much money on said items, it was time to depart. We were on our way to the last stop, dinner at a Tuscan farmhouse /winery /castle in Chianti…if this day could get any better.

Our guide/driver Christian was terrific. Anna and Micky feel in love with him. He was so attentive and even stopping along the way to see some wild boars. He was a joy to be with all day. Once we arrived at the farmhouse, we are escorted downstairs to the wine cellar. They had a fantastic set up waiting for us.

All and all this was the right choice. This tour. I am not one for group outings but, Florencetown does it right. Small group VIP all the way. We actually ended up meeting another couple on the tour that lived one neighborhood over from us. What are the odds of that! It was an amazing experience that I recommend to all my clients visiting the area.

Tour rating: 5/5 One of the best I have ever been.

Florencetown Tours: 5/5 Christian was AMAZING and the service was impeccable.

San Giminago / Siena / Tuscany : Duh… 5/5 !

Happy travels!

Hi, I'm Tracy Kirssin Hanes

For over two decades, I’ve helped my clients explore and experience the world by seeking out the best it has to offer and sharing it with them by creating bespoke dream vacations. As a travel consultant, my work is so much more than booking hotel rooms, securing a rental car, and juggling a lot of logistics. (Though, of course, I take care of all that stuff too.) It’s about lining up those one-of-a-kind experiences that make you fall in love with a new place. All you have to do is pack your bags.

Nice to meet you!