From all our homemade pasta nights, we knew immediately that Italy would have to be on our agenda for our honeymoon. We could not think of a better destination to enjoy Italian food, explore the Tuscan countryside, soak in the sunshine, and immerse ourselves in the laid back culture. When we started our travel research, we were surprised to learn just how many places there are in Tuscany to explore. We narrowed down our search to Southern Tuscany and we are so glad we did! We have collected recommendations to maximize your time in Tuscany, including a list of must see towns of Southern Tuscany.
Why Southern Tuscany?
While there are endless beautiful regions of Tuscany, we choose to explore southern Tuscany for an authentic and tranquil experience. Many people stay in northern Tuscany, towards the Chianti region, as it is easily accessible from Florence. However, if you are looking to avoid the crowds while enjoying the beautiful countryside and medieval towns, then southern Tuscany is the perfect choice!
How to get to Southern Tuscany?
Because Tuscany is such a large area to explore, it is recommended to rent a car to get around. We rented a car from the Florence airport. Driving in Italy was stress-free, especially once you get into the countryside. It is important to note that Italy requires an International Driver’s license. We secured our international license through AAA and these licenses are valid for one year.
Roadtrip through Tuscany
On the way to Southern Tuscany, there are some must-see places to stop on the drive and a good excuse to stretch your feet.
Chianti Region:
A stop in the Chianti region is an absolute must! Not only is this area known for some of the best wines of all of Italy, but the rolling hillsides are stunning. We stopped for a wine-pairing lunch at Azienda Agricola Casa Emma. This charming vineyard was the perfect introduction into Tuscany. The Chianti wine we tasted here ended up being our favorite wine of the entire trip! And for a very memorable dessert, we tasted a white grape gelato with aged-balsamic drizzle.
San Gimignano:
Unfortunately, we did not have time to stop here, but it is top on our list to visit next time we are in the area! We have heard that San Gimignano is a favorite, to explore the picturesque streets and hilltop views.
Where to stay in Southern Tuscany
It can be overwhelming picking accommodation in Tuscany because every hotel looks like a fairytale. We recommend trying to stay close to Pienza and Montepulciano for a central location to explore the region. We complied a list of our top choices when narrowing down the search, as well as where we decided to stay.
Reccomended accommodation
- Lupaia: a luxury resort hotel near Montepulciano
- Cugusi BnB: bed and breakfast near Montepulciano
- Salcheto Winehouse: boutique accommodation on a vineyard near Montepulciano
La Moscadella: our top choice for accommodation in southern tuscant
We cannot speak highly enough about our stay at La Moscadella, a bed and breakfast nestled in the hills near a very small town of Castelmuzio. This boutique hotel was a previous monastery turned into a beautiful accommodation. It is a small family-run business that accommodates up to 30 guests. The privacy and tranquility of this bed and breakfast, yet a close drive to the nearby towns of southern Tuscany, was irresistible.
We absolutely loved our experience here! Each morning we did a quick jog to a nearby town of Montisi, enjoyed a cappuccino, and ran back to indulge in the complimentary breakfast. We also participated in their homemade pasta making class where we learned how to make hand-rolled pici pasta. We quickly discovered that hand-rolled pici pasta was a lot more work than our usual pasta machine! But the final product was to die for and obviously so worth it. Another fantastic amenity that La Moscadella offers is e-bike rentals. We rode our bikes along the countryside and stopped to explore the neighboring towns.
The days were spent slow, soaking up the sunshine and the incredible views of the countryside. Exploring Tuscany involves touring the neighboring towns, all perched atop hills which allowed for defense against oncoming militaries back in the medieval times. These are some of the towns we visited:
Towns of Southern Tuscany
Pienza
Pienza is the dreamiest city we visited in Tuscany! It is so picturesque with the cobblestone steps, winding streets, and views of the surrounding vineyards. We spent hours just sitting on the steps, eating gelato, and gazing at the vast rolling hills. Just 30 minutes outside Pienza, is Podere Il Casale, an organic farm-to-table restaurant with the most incredible views. We had such a special night here, tasting fresh cheese from their farm (literally hearing the sheeps) and tasting the freshest vegetables. The sunset here was phenomenal. I truly hope we will be back here one day!
Montalchino
The wine region around Montalchino is known for their unique Brunello wine. To our surprise, we actually did not enjoy this wine varietal. It has a very distinct and bold taste. But the town of Montalchino is beautiful to walk around!
Val d'Orcia
This is the famous winding road aligned with cypress trees that is so often photographed. We of course pulled over and snagged a few photos. On our drive, we visited Poggio Grande, which is a small family-owned winery that was recommended to us by our bed and breakfast. Not only were we blown away with their delicious organic wines and olive oils, but we loved how personal this experience was. It was just the daughter of the wine-maker and us, learning about their family stories.
Montepuciano
Montepuciano, not only is a fun Italian word to pronounce, but is a stunning town to visit! We first started at Cugusi cheese farm for a picnic with a hand-picked selection of pecorino cheeses with a view overlooking the town of Montepuciano. We then walked through the town exploring all the stores and wine tasting rooms. Our favorite tasting room was Boscarelli in Citta.
Florence Recommendations
We first started in Florence where we stayed two nights, mostly to enjoy delicious food and walk the cobblestone streets. Our Airbnb was located along the Arno river, on the opposite side of the main city center. We loved this location because it was a 10 minute walk into the heart of the city, but also away from the hustle and bustle. And not to mention our Airbnb was perfectly located a door down from the best gelateria in town (Gelateria La Carraia) which we of course visited each day!
In regards to food recommendations, Osteria Pastella for dinner is a must! They are known for their truffle pasta made in a cheese wheel. We honestly think about this meal often. You need to make dinner reservations weeks in advance, but you do not want to miss this!
A trip to Florence would not be complete without a panini lunch at All’Antico Vinaio. Our panini came with a pistachio pesto spread that was to die for.
And of course, coffee. We started each day for coffee at Ditta Artigianale Neri. They have various locations throughout town and had some of the best pour-overs we found in Italy. After grabbing a coffee and freshly baked croissant, we started our day with a morning run up to Piazza Michelangelo. This was our favorite view over the city of Florence!
