Tuscany Day Trips + Wine Tasting

t u s c a n y

Our second half of our holiday trip in Italy was in a small village called Gebbia, outside of Civitella in di Chiana. We arrived a bit early, so we explored the almost abandoned Civitella. After our short walk around the city, we drove up the hill about 15 minutes to our even smaller village.

While waiting for the Airbnb host, we opened a bottle of wine and enjoyed it with some cheese and prosciutto while taking in the amazing view. It wasn’t too long (a bottle of wine later) that our host arrived and showed us the unit.

We absolutely loved the serenity. A drastic change from the streets of downtown Florence. No screeching ambulances or people yelling at three in the morning. Just peacefulness. It was all great, until we attempted to access the internet. This was a mandatory item due to work, so with some power lines down, we had to find a backup plan.

The next two evenings were a bit eventful trying to make sure each place had a decent connection. That evening we scurried over to a hotel in Arezzo for the night. And we witnessed the most beautiful sunset…

s i e n a

The following day, we scheduled another day trip to Siena. It was only about an hour drive from Arezzo. A much bigger town with a little bit more action going on.

We climbed the tower to have a 360-degree view over the city. It was a bit chilly, but beautiful. Afterwards, we roamed the city streets, checking out all of the history and old architecture.

On another recommendation, we stumbled upon Antica Osteria da Divo for lunch. We debated as the kitchen had just opened, but since they usually seat based on reservation, we didn’t want to miss the opportunity. And I would have to say that hands down that was the best service that we had our entire visit. Our server and sommelier took great pride in everything. Our food was prepared perfectly, and the presentation from the wine to the dessert, was beyond excellent!

The following few days were relaxing. We didn’t have any crazy New Year’s Eve plans, so we researched different events around our village. And as a last minute decision, we made reservations in the small Civitella by Gebbia.

NYE was definitely unexpected! We had dinner plans, but didn’t know what we were getting ourselves into. The woman who took our reservation suggested nine, but didn’t give an explanation as to why, so we asked for an earlier time and she agreed. When we showed up for our reservation, the restaurant door was still locked – which we thought was unusual, but not completely out of the ordinary considering everything we had run into thus far.

A woman proceeded to open the door where we were led in to choose our table. At this time, our waitress (who spoke English) explained how NYE dinner works – they do not have multiple reservations, but rather the gathering is intimate and a celebration. They plan the evening completely from start to finish, from nine to midnight. We were provided a NYE menu, in which we thought we would choose from the pre-fixed menu… we were wrong. There were 12 items on the list, and we got to eat everything! After about the third appetizer, I was full, but we had so much more to go.

When the dessert comes, it is customary to go outside and watch the fireworks and toast champagne in the streets and then return to your table for your last glass of champagne and then an expresso or cappuccino. We didn’t realize until the end of dinner, that we were on the floor with the owner’s family. So, needless to say, we stuck out like a sore thumb. But we had so much fun, and will forever cherish the memories and tradition we experienced.

The next day, we had a full day planned ahead for another day trip. We adventured off to Montepulciano, Pienza, and Montalcino. All pretty close to each other.

m o n t e p u l c i a n o

Montepulciano was bigger than expected! We were traveling in off-season and here it was the most noticeable. We ventured off into the streets and came upon our first wine shop. After browsing around, we were invited to visit their cave below the storefront. This was awesome! It not only was a wine cellar, but basically a museum. Full of old farm tools, an olive making press, and aging cheese! A very awesome and unexpected adventure!

After this, we decided to explore more of the town. I had allotted two hours, but apparently we needed a bit more. So, unfortunately with our meter running out, we were unable to stop in any of the winery shops to do a tasting. This is one town I would like to see during the on-season – so that will be another trip to plan for.

p i e n z a

After Montepulciano, we headed down the road to Pienza. I read that it was maybe nine blocks long, so I knew we wouldn’t be here long. Especially considering how the last city was.

Alas, I was completely wrong. This little town was full of tourists! We attempted to go into a couple cheese shops to get some of the Pecorino cheese they are famous for, but were not welcomed by any means. So we walked the streets and took some pictures and grabbed some cheese on our way out from another (not so famous store). Overall, a nice, quick visit, but the experience could have been better.

c h a p e l  o f  o u r  l a d y  v i t a l e t a

From Pienza to Montalcino, you are driving through beautiful tuscan hills, sprinkled with cypress trees and old farm houses. As we were driving, we came across the Chapel of our Lady Vitaleta. We originally thought we had already missed it, so we were excited when we saw it in the distance. It was so amazing to see this in person!

m o n t a l c i n o

Next stop, Montalcino! I thought this town couldn’t possibly have as much charm as Montepulciano, considering the size, however, I was way wrong. They had a bit better view from their hilltop and a beautiful tower with their Christmas tree out front (still playing Christmas music)! But just as many stores were closed (more closed than open) but we managed to run across a wine bar, which thankfully we had a young gentleman there, Paolo, help us out.

After a small tasting, we walked a few doors down to a restaurant which had a magnificent view. Our server paired our lunch with a tasting of their Brunello wines they are famous for. The wine and food did not disappoint! After our late lunch, we explored the empty streets until sunset. I would definitely visit again!

w i n e  t a s t i n g

c a p a n n e l l e

g a i o l e  i n  c h i a n t i

Poggio Antico in Montalcino and Avignonesi in Montepulciano were both recommended wineries. Unfortunately, they were both not available due to it being off-season during our visit. So, on another recommendation (and another day), we were able to make a reservation at Capannelle in Gaiole In Chianti. 

Almost impossible to find, but we managed to get their right on time! Once we arrived, our host introduced herself and immediately started the tour. Their boutique winery also offers a small resort for a short stay or special events.

The tour included a brief overview of their grounds and history before we proceeded downstairs. Here, they make wine, store their barrels + aging bottles, and a very VIP wine vault! We learned a lot about the details that are included in their process.

After the tour, we were taken back upstairs where our tasting was to begin. When we made a reservation, our initial thought was due to the low-season, they wanted to make sure they had the appropriate staff. However, we had no idea that you get your personal one-on-one host to take you through the process! It was such a genuine experience, and honestly, I wish all wine tasting was done this way!

Such a great experience being able to travel through the tuscan hills and visit so many villages. Each adventure was unique in it’s own way and I loved every piece of it.


c h e e r s

You may also like


  1. I absolutely love your posts, how you structure them, how you tell the story of each experience accompanied by so many awesome pictures. Each time I see these posts, read the stories, and stare in amazement at the pictures you captured and the beauty that is Tuscany, I relive this incredible trip ever time. Thanks for that 🙂

    1. Thank you, Mike! It’s hard to capture all of the beautiful moments and put them into words – I hope the post encourages everyone to experience it themselves!

Leave a Reply

Your email address will not be published.

Time limit is exhausted. Please reload the CAPTCHA.