Getting there
As part of our most recent Europe trip, we included 4 days in Southern Tuscany with our toddlers (3.5 and 1.5 at the time). It was Fall and the weather was perfect, no rain and such comfortable weather. We were there in late September and while I would consider it a shoulder season – the towns were still lively, but it felt so comfortable and not crowded. I would highly recommend visiting this time of year.
We arrived in Tuscany via a rental car we picked up at the end of our time in Florence. The drive was straight forward, with just one stop in Siena for a snack and to stretch out legs, before arriving at our accommodations near Pienza.
Note: We know that Florence is technically “Tuscany”, but we have shared our favorite things to do in Florence with young kids here. We will focus more of this Tuscany guide on the smaller towns we have visited and enjoyed.
Accommodations in Tuscany with Toddlers
Hotel/ Agriturismo / B&B
We put these lodging categories together because all of them typically have a property host (owner/staff) that will check you in, answer questions, and be available on site during your stay. These properties also tend to have dining options, housekeeping if requested, and some other conveniences (soaps, toiletries, concierge, etc.).
Hotels and B&Bs are familiar to most people, but an Agriturismo may be a new term for you. The Italian roughly translates to agriculture tourism, but don’t let that steer you away. An Agriturismo is an Italian country home/farm with a agriculture product on the property (think olive oil, wine, cheese, etc.) that is also open to host guests for meals, accommodations or both.
Given the broad definition, Agriturismo accommodations can range from basic/rustic to elegant and resort-like. This has been my family’s favorite way to stay in Tuscany with toddler’s. Agriturismo’s are easy to find as they are on all of the major booking sites (Expedia, Booking.com, Airbnb, VRBO). You can really tailor the property to include everything you need (there are around 20,000 registered Agriturismo’s in Italy), in addition to getting to experience the agricultural element on site.
We stayed and would highly recommend Tenuta Santo Pietro, a winery and olive oil Agriturismo. We did a truffle hunt with a puppy, enjoyed authentic and delicious Tuscan meals on site, drank wine and cocktails on the patio, walked the property to see the chickens and bunnies, and relaxed by the pool. The extra special part of our stay was the amazing service. We loved the manager (Bertina) and all of the staff, who were so friendly and warm to our whole family. The location was also perfectly situated between Pienza and Montepulciano (two towns we like to explore), and a 30 minute drive to the wine town of Montalcino.
Vacation Rentals (apartment/condo/home)
Vacation rentals can be great if you want to make your own meals, do your own laundry, and/or you prefer to have your own space. Additionally, vacation rentals give you the ability to stay in the middle of Tuscan towns (sometimes even more so than a hotel).
Having the above amenities in a vacation rental does come along with some other potential tradeoffs. Laundry isn’t always available in every vacation rental and finding a dryer is even more rare. Parking is not always included and check-in or questions during your stay can be a little more ad-hoc since you don’t have a host on site. Given that you have your own space (and typically more of it), many times vacation rentals can be the more expensive option, so keep fees and taxes in mind when browsing options.
Tuscan Towns/Villages
There are approximate 275 towns in Tuscany, and too many good options to list, as each place has something different to offer. Below is a small list of some of the favorite places we have visited.
Pienza
Pienza is a small, hilltop town, known as the “ideal city of the Renaissance” and for Pecorino Toscano cheese. The town is easy to walk, has beautiful views over the Tuscan countryside, a variety of restaurants, gelato (we loved Buon Gusto Gelateria), and easy parking just outside town (marked by signs). The town can be explored in a day but has enough culture that a longer stay would be really enjoyable.
Montalcino
Montalcino is a small, hilltop wine town known for its Brunello wine (Sangiovese varietal). This hilly town has cute streets, a Fortress and opportunities for wine tasting on most corners. Our favorite place to taste inside the town was Enoteca di Piazza wine room, which has over 100 local wines to taste every day “on tap.” We took advantage of the free international shipping on most of their bottles, and they arrived in Seattle in perfect condition. Highly recommend versus trying to bring wine back in your luggage. The shop was also a great place to wine taste in Tuscany with toddlers because the location is on a pedestrian street, which made it easy for an adult to take the kids to stretch their legs and explore the nearby shops.
Outside the city walls (traveling by car or tour) they are lots of amazing wineries to visit. While there are too many to name, we enjoyed Castello Banfi and Ciacci Piccolomini d’Aragona. We always suggest giving the winery a call before arriving to make sure that they can accommodate you.
Montepuliciano
Montepulciano is another hill-top town known for its Sangiovese wine (Vino Nobile di Montepulciano). However, this town has more to offer than just wine. Good restaurants, amazing views of the surrounding countryside, quaint town squares, a large grocery store, and its own Fortress with a pleasant garden. Additionally, there is a playground on the edge of the town that our toddlers loved. While there are too many wineries to name, Canneto was our favorite. Canneto is located outside of the main town on its vineyards, but you should also be able to find its wine in the towns restaurants and tasting rooms.
We adored our visit to southern Tuscany with our toddlers and can’t wait to go back to explore more! Share any of your favorites below, I would love to add them to our next visit.
