Chianti and Tuscany are debatably my favorite parts in all of Italy.  I had the most amazing time in this countryside. A lot of people go to Italy and try to hit all of the major cities and overlook the countryside.  Please don't, places like this is what truly makes Italy so special.


The Activities


I used this company for a full day tour of bike riding through Chianti. I was picked up at the home I was staying in, driven to their bike shop, had a quick tutorial and was

on my way with the owner guiding our group. We used the electric bikes which is highly recommended!! The hills in Tuscany are no joke and the motor gives you the push you will definitely need! We had experience bikers in our group who tried not to use the motor but still needed it in the end.  With the motor the bike ride is extremely enjoyable and maybe just a little challenging. Our guide, Alex, was very friendly, knowledgeable, spoke great English and took us on the ride of a lifetime! We rode for about an hour+ before stopping at the first winery. The ride was absolutely amazing, definitely a bucket list to ride through the hills of Chianti! We stopped at two different wineries and had the most amazing time. We were given tastings, tours, food, etc. The whole experience was absolutely wonderful. When our group decided to buy several bottles of wine and olive oil, they showed up in our van that drove us home for the end of the tour so we never had to worry about carrying anything. I think this company is still growing so we were happy to be a part of their journey to come. All the best and success to this amazing tour company and if you are in Chianti, this is definitely the place to go exploring with!! Below is some information on the wineries I went to:


I arrived at this winery, and was immediately greeted by the amazing staff.  My group was offered a table outside where we were given light snacks and a wine tasting. 

All of the wines were delicious!  We then took a small tour of the winery.  I had the best experience here and ended up buying a lot of wine and olive oil to bring back home.  I still have a few bottles left and am saving them for something special!


This was the second winery on the tour where I had a sit down lunch.  Everything was very tasty and lunch was accompanied by another great wine tasting! After that, I had a guided tour of their 600 year old winery and the Niccolo Machiavelli’s house.  It was interesting to learn more about Italy’s history and Machiavelli. 


This was a winery in the certified Chianti region where we were treated to a special private tour and tasting.  This winery produces specializes in delicious red wines.  This was one of the more expensives winieries we went to, but it was a great time.  The owner and son of the vineyard spent a lot of time educating us on their process.  This was not part of our biking tour but was another special winery we visited.

The Food

My family and I were recommended to visit this restaurant and we had an open afternoon and decided to go for lunch. We traveled all over Italy for 2 weeks and this was quite possibly our favorite meal of the entire trip! It was truly amazing! The Florentine steak was more affordable and tasted much better than the steak we had at a very famous restaurant in Florence!! The Beef Peasant Stew was one of the best things I have ever eaten. The flavor was unbelievable! The restaurant is family run and completely authentic. The daughter running the store was extremely nice and helpful in providing suggestions to order. When we were leaving her father even handed us a piece of delicious apple cake. Everything is cooked with simple, delicious ingredients. The restaurant is also very cozy. I wish I lived around here so I could go back to this restaurant every day. If you are in the area, you must go you will not be sorry!! This is a picture of the own/daughter of the restaurant cutting and preparing our Florentine steak!


The home I stayed in (details below) did a cooking class for us where we made a fresh pasta, sauce, the meat and the dessert.  It was an incredible experience and fun to learn a little bit more about living completely local!

The Lodging


Where can I possibly begin? Our stay was absolutely wonderful at this property and you should look no further! My family and I stayed at this villa on Jessica and her family property for 4 nights, 5 days. We probably could have stayed a month. From the second we arrived, we were made to feel like family. It was also really great that Jessica was available to us even before we arrived. We had some questions about bike tours, wine tours etc. and she was readily available to provide a recommendation, which by the way, we ended up being so happy with! The home itself is lovely. It is one single home however it is a bit broker up with two different entrances to two separate living spaces, kitchens, bedrooms etc. This would be a great set up for two families traveling together. Since we were one family we were a little split up but it didn’t matter. There is a large glass window room overlooking the property that can seat 10-12 people easily. There are also separate lounge areas outside including by the beautiful pool! The house also has a wine rack of all of the wine that Casa Di Monte produces which we took full advantage of! You can take whatever wine you want and just pay at the end and the wine prices are more than reasonable! There is also homemade olive oils that are a must try as well! On the day of our arrival, my family and I went to Jessica’s house from a Pizza dinner where her mother in law, Antonella made homemade brick oven pizzas that were fantastic! Obviously this is a very special place. In regards to location, it is in a very small little town in Chianti, about 45 minutes from Florence. The bike tour we did was out of a town called San Casciano which was about a 40 minute drive away. The town of the property itself has a grocery store, some bakeries, restaurants etc. so it doesn’t have really all you need to make it your home base for however long you are there! Overall, everything about our stay was amazing but it is very obviously that it would not be the same without Jessica. She will make you feel right at home just like she did with us which made all the different. Enjoy!!

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© Pamela Loria Pennisi