Planning a trip during the transition between fall and winter may seem like a risky move. But in my opinion, as long as you know that you may have to brave some less-than-favorable weather elements, your travel flexibility will be rewarded with:

Cheaper airfare
Cheaper accommodations
Easier ability to reserve experiences
Less crowd to fight against

Even with the good things, you’ll still need to be aware of some potential issues:

Irregular hours for restaurants or other experiences
Shop closures
Weather affecting plans

All that being said, I still thought it would be a wonderful experience to experience Europe in these cooler months, since I had only ever been in early and late spring. So when Will and I started discussing potential honeymoon options, we thought a cozy two weeks in Europe sounded much more like our speed than a tropical getaway. So we planned for a trip to Tuscany as part of the trip and Will picked to focus on Pienza.

Travel to and From Pienza

We flew in directly into Rome from Paris on Vueling, since we started our trip in France. Once we landed in Rome, we went directly to pick up our rental car from SIXT, which was fairly easy to find once we found the right signs. They were able to help us secure a Fiat XL. Originally, we had hoped for the tiny Fiat for the whole Italian experience, but we were happy for the larger vehicle when it came to climbing up and down the valleys and driving through some rain storms.

Once we got our car, we headed out on the highway out to Pienza! It took us some time to start to get into the countryside, but once we were driving out there, we could not believe our eyes. The scenery looked so much like a painting everywhere we looked!

We came across a few toll roads while driving where we realized you took a ticket from one, and then when you either exited or completed the length of the toll, you inserted the ticket into the machine and paid the tool. We were able to use our credit cards on the machines too.

On our return, we opted to our car in Rome proper, rather than head out to the airport and then go back into Rome for the rest of the trip. We found the return location a bit precarious - luckily, the SIXT attendant had given really incredible details for the drop off or we would have never, ever found it. We also had some difficulty finding a gas station that we could use. We found some problems using our credit and debit cards at the station (something about them not taking chip cards) and a lot of the stations in Rome did not have attendants, so we couldn’t use cash to pay.

Driving in Rome was definitely an experience and I am definitely glad it was not me behind the wheel. Google Maps was pretty accurate and we were able to find where to drop off the car.

Pienza Hotel: Hotel San Gregorio

Our goal while driving to Pienza was to arrive before it got too dark - driving on these tiny, wet roads in the dark was not what we really wanted to do! We arrived right around dark fall at Hotel San Gregorio.

We booked this hotel with points from our Chase Sapphire Rewards card (which is what did for all of the hotels on this trip) and were so pleased with it. We were warmly welcomed by the front desk by one of the family members who owned the hotel. The hotel had included parking, which was excellent for us! We were then showed the hotel room, which was a lovely suite set up with a living room and dining area. All the rooms have a type of spa-tub set up (some more elaborate than others) which really added a cute addition to the stay. The hotel staff was also incredibly friendly and helpful. They gave us recommendations for nearly anything we asked for

Since it was mid-week and off-season, you could definitely tell that things were a bit more quiet and cozy. We didn’t see too many other hotel guests around or, when we ventured outside, too many other travelers.

Things to Do in Pienza

Wine Bars: Once settled in, we braved the rain to start to venture around to a wine bar walking distance from the hotel. Pienza491 has a friendly owner and a huge selection of wines. You can do a set tasting, or pick your own glass or bottle to share. In addition to our wine, we were also treated with some delicious bites of bread, olive oil, and salami. We also got a quick lesson of local wine regions and what to keep an eye out for.

City Center Strolling: We also really enjoyed walking around the Pienza city center during the day time. Be warned - hours were not as expected and many places opened late or closed early. Walking around the cobblestone pathways and dipping in and out of little alley ways was made extra special in the rain. We also stopped in Montalcino, and walked around another similar city center, only this time it had a castle that we paid a few euros to walk around the top and snap pictures of the incredible view.

Cooking Class: One of our must-dos on the trip was to take a cooking class. Will found Podere il Casale, and we opted for a group cooking class - which ended up being a private class! Sandra shared her passion of the ecosystem of the farm and we were able to learn how to make a traditional Italian meal - pici pasta, tomato sauce, pesto, pork loin, and then dessert! After preparing the elements, we took a farm tour and then was treated to a lunch of what we prepared, with some extra treats. My favorite piece was the incredible cheese tasting plate! Also, the views from this location are unbeatable. From the outside seating area, you can actually see a spot that they filmed Gladiator!

Wine Tasting: Obviously you can do plenty of wine tasting in this region! We were told that during the high season, reservations are a must. During this low season, it wasn’t hard to get reservations, but it was critical to check that the wineries were open. We visited Avignonesi and the tour was truly memorable. The explanation of the vin santo process (and seeing all of the grapes drying) was so unique and so unlike anything else we have seen before. The estate tour was great and the tasting so thoughtfully done and paced out.

Overall, we recommend doing to Tuscany during the off-season! It was a mystical, quiet experience that allowed us to self-paced our adventures rather than felt like shuttling from one location to the other.

Where else would you recommend going during our next off-season trip?

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