When we started researching our first trip to Tuscany, all we could find was information on agriturismos, which sounds lovely, but wasn’t what I was going for at all. After a lot of research, I stumbled upon a few romantic hotels in Tuscany and Umbria. These particular hotels have helped me fall in love with these beautiful regions, and my list of hotels to try grows a little bit longer with every trip.
Palazzo Carletti in Montepulciano
Palazzo Carletti was our gateway into exploring Tuscany by car. There are five rooms in this former palace and we’ve stayed in three of them (four, if you count the room my mom stayed in). It’s located in the heart of Montepulciano, a gorgeous hill town in the heart of Tuscany. The Albany suite is my favorite because it provides a beautiful view of the countryside. We enjoy watching the Tuscan sunrises and sunsets from this room.
Montepulciano is great for wine tasting, delicious meals, a lovely Christmas market, and enjoying the views. You can drive the scenic Val d’Orcia but there are infrequent buses between Montepulciano and the smaller villages. Make sure your Tuscany packing list includes clothes for any type of weather. You can have all four seasons in a single visit to Montepulciano!
Bonus: All rooms include free parking and breakfast.
La Terrazza Sul Campo in Siena
If you are looking to experience a bit of Tuscany without a car, hop on a train and spend a few nights in Siena. La Terrazza sul Campo is part of an Italian trip itinerary that I dubbed Rooms with Views. With four of their five suites overlooking the Piazza del Campo, you can appreciate the beauty of this beautiful square from the comfort of your beautiful room. Room rates include made-to-order breakfast served ensuite, which means you can watch the sunrise over Siena at your leisure. I would love to book one of these rooms for the Palio.
Tip: If you’re a light sleeper, consider booking the Il Pulpito suite that overlook the interior courtyard. You get the benefit of the location and silent quiet evenings when you’re ready to rest.
Nun Relais Spa & Museum in Assisi
On a spring trip to Italy, Assisi was one of our last destinations before flying home from Rome. The Nun Assisi proved to be the best place to spend a few days and unwind before jumping into a packed Rome itinerary. Not only did we have Assisi to ourselves before the tour buses arrived and after the day trippers left, which made for extra romantic walks, we also very much enjoyed the spa facilities. The hotel is located in a quiet part of town and is only a short walk from the major sites.
Tip: Have the spa staff explain the entire spa journey and try to follow the pathway. It’s a great way to relax, release toxins, and get a GREAT night’s sleep. We loved the spa staff!
Borgo dei Conti Resort in Umbria Countryside
Okay, so technically, this hotel is in Umbria. Borgo dei Conti is on the border of Tuscany and Umbria, separated by a park and a lake. We’ve used it as a jumping off point to explore southern Tuscany, as well as a way to explore some of the great hill towns of Umbria. Borgo dei Conti is one of the most romantic hotels in Tuscany when you want to get away from everything. Literally, everything. Located in the hills, this resort requires a car to explore the area. The resort offers numerous athletic activities including tennis and swimming, but it’s also a great home base for exploring the area and experiencing Umbrian wine and olive oil. The superior rooms are extremely romantic and I am excited to try one of their new junior spa rooms!
Bonus: Room rates include spa access. Take advantage of it! It’s the perfect way to start or end the day. We love going between the jacuzzi, the plunge pool, and the sauna. I’ve also had lovely massages here. The lavender and lemon bath salts are my favorite hotel bath product anywhere. 
Read more about our Favorite Hotels in Tuscany!
More Romantic Hotels in Tuscany & Umbria
If this is one of your first trips to Tuscany and Umbria, I definitely recommend staying in one of the hill towns and getting accustomed to the slower pace of life. (It can be hard for Americans, particularly at first!) From there, you can start venturing out to the more romantic hotels in Tuscany and Umbria. We had to cancel a few trips in 2020, but here are a few hotels that we visited in 2021 and 2022 – as well as one that is still on my wish list!
Borgo Pignano near Volterra
Borgo Pignano was really high on our list for our last trip to Italy. Tom and I fell in love with the Volterra countryside on a winter trip after experiencing the most magical sunset that I’ve ever seen. Borgo Pignano offers cooking classes, wine tastings, a spa, and plenty of other outdoor activities. It was an absolutely lovely place to relax and immerse oneself in Tuscan countryside life.
Monastero di Cortona Hotel & Spa in Cortona
We’ve visited Cortona 4 times since June 2021. The Monastero di Cortona Hotel & Spa is the perfect location for exploring the area and balanced our trip with a lovely Italian spa experience. Interestingly enough, Cortona is essentially right across the lake from Borgo dei Conti, so it is really nice to have a spa hotel option that is located in a village that is easily accessible by train and doesn’t necessarily need a car to explore!
La Bandita Townhouse in Pienza
La Bandita Townhouse is located in the quaint village of Pienza. We’ve spent a lot of time exploring Pienza on previous trips, but we’ve never stayed there. There are a number of restaurants and agriturismos in the area that we want to try, so I think this could be a great home base and a chance of pace from Montepulciano. (The best gelato in Tuscany is in Pienza, too!)
I know I’m missing more than a few hotels because I have more than a few more saved. Do you have a couple of romantic hotels in Tuscany that you love to visit? What about Umbria? Drop them below so I can add them to my never-ending list!
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