6 Ways to experience real Tuscany with your family
You don’t have to do much to have a wonderful time in Tuscany. After all, it’s Tuscany - land of picture-perfect hill towns, cypress-lined back roads, and simple culinary pleasures. However, if you’re open to exploring beyond the well-loved favorites, you can find moments that you’ll be able to truly call your own. It’s the bit of Tuscany that we can often miss.
1/Get lost in history
If you’re willing to schedule time to let adventure happen, you’re almost guaranteed to be rewarded in a place as historically rich as Tuscany. My family's most interesting experiences always occur when we put away our smartphone map and “get lost” on the narrow back roads, where even in high season, the crowds fall away, and we seem to have Italy to ourselves. Our favorite find was Badia di Passignano, an abbey built in 1041 as a stopover for pilgrims passing through Tavarnelle Val di Pesa in the province of Florence. Five monks of the Valleombrosian Order look after the abbey and open the fortress-like compound at 3 p.m. daily. They provide a surprisingly intimate tour of the historic site that may look modest from the exterior, but once inside you’ll find a seemingly endless source of awe-inspiring moments, highlighted by a massive fresco of the last supper painted in the 15th century by one of Michelangelo’s teachers, Domenico Ghirlandaio. It’s out of the way and a bit hard to find the entrance, but it’s completely worth it.
After your visit to this refreshingly rustic abbey in the heart of Chianti, walk across the road and enjoy a contemporary take on Tuscan fare with a meal at the family-run Ristoro L’antica Scuderia in the shadow of the bell tower and overlooking vineyards. The prices are reasonable, the service is wonderful, and the setting is surprisingly refined given the rustic location.
2/Trade four wheels for four hooves
If you’re looking to get even further off the road less traveled, try horse trekking through the hills of Tuscany. This unique way to experience the region’s classic beauty gives riders of any skill level a moment to slow down and see Italy from a timeless perspective. The Il Vecchio Maneggio Agriturismo in the heart of Chianti offers families the chance to come to a working farm, enjoy a coffee on the patio, and sample the farm’s many varieties of honey while they prepare for the trek. Then you’ll head out into the surrounding vineyards and forests for views of the surrounding valleys or nearby San Gimignano’s stone towers from atop your trusty mount. The experienced guides lead the way, and the stable of veteran horses make it an easy family activity that won’t soon be forgotten. Book through Fun in Tuscany, and for about $125, they’ll pick you up in Florence (if needed) and take you out into the hillside. Then it’s up to San Gimignano via minibus for a close-up look at the medieval city and to a nearby winery for an afternoon of tastings for adults and activities for the kids. Trust me, you won’t be disappointed.
3/Rent a villa with history
There are villas to rent by the hundreds online, and it can be overwhelming to find one that will give you an experience that not only meets your needs but also gives you a few stories to take home. We recommend Casa Greve, also known as Villa Bonci, a beautifully restored rustic stone farmhouse with a pool on the edge the small village of Gretti near Greve in Chianti. The original structure, dating from 1410, was built as a country house for a Tuscan princess and is now owned and run by Anna Bonci, a former international fashion designer-turned-local hostess who lives in an adjacent apartment on the property. Having an on-site hostess proved to be an invaluable resource, and we’d highly recommend finding a location that includes a local to help connect you with the rest of the community. Hearing the owner’s stories about the home’s history and the trials that came with bringing a 15th-century structure into the modern age was amusing, to say the least. The kids loved knowing all facts, such as the series of small sitting rooms on the ground floor were formerly livestock stalls. Anna was incredibly entertaining and her ability to call a friend and arrange a last-minute dinner reservation at his restaurant was just one of the valuable perks. We worked with rentvillas.com to find our perfect bit of history, where the aqua blue hillside pool may have replaced the farm’s pond some years ago, but the spirit of a small rustic farmhouse with well-worn stone floors and shelves filled with antiquities delivered lifelong memories.
4/Turn market day over to the kids
Market day in Tuscany is a spectacle of abundance and timeless craft. These colorful gatherings are great ways to get a real sense of the place and feel the energy of the community especially in the smaller towns and villages. It’s also an opportunity to get kids involved and out of their comfort zone by letting them do the shopping! It turns an often passive experience into a scavenger hunt of sorts. In our case, we collectively discussed what we would cook that evening and then armed the kids with a loose shopping list, a budget, and a few key phrases and basic numbers, as well as some insight into how the market works and general etiquette. The bustling stands and myriad of unique choices can be overwhelming initially, but you’ll be amazed at how their sense of pride builds and as the bags of fresh produce and local hand-crafted specialties add up. The stand operators appreciated the kids taking the time to attempt their orders in Italian and usually resulted in some pretty memorable interactions. Even when their Italian fell short, the ensuing game of charades was equally as effective and often fun. Our favorite market was the Sunday market in Panzano. Since most of the stores in rural Italy are closed on Sundays, it made for a great day trip and filled our kitchen with some wonderful ingredients for that evening’s meal. In the end, the exercise proved exhilarating for the kids and when dinner time came around, their sense of accomplishment was almost as sweet as the local hand-picked fruit!
5/Be a regular
It’s simple, but there’s really no better way to get to know the people of Tuscany than engaging them on their terms. Returning to a shop over and over will quickly break down barriers and get you in good with most local shopkeepers or baristas. Just visiting alone won’t do the trick, but arriving with a small arsenal of conversational Italian and taking the initiative will help greatly. And when I say small, I mean the absolute basics - no language classes needed here. Italians are quite proud of their language and even more protective of the many local dialects that are more distinct than one may think. So a pleasant greeting of “buongiorno” in the morning or “buona sera” in the afternoon will easily knock down that first wall and let them know that you’re respectfully acknowledging their culture. A question when browsing as simple as “in Italiano?” and then repeating the Italian name gets things going even more, and hey, it’s like getting free Italian lessons! Over and over, we found that showing a willingness to try, no matter how poor our pronunciation, was repaid with a forgiving exchange and usually lead to more great local recommendations or even personalized experiences that got us one layer deeper into the real Tuscany.
6/Let a Tuscan do the cooking... or teach you how
Eating amazing food is undoubtedly a part of any Tuscan vacation, and the options for great dining out are seemingly endless. Heck, even the highway truck stops take their cappuccinos and cheese cases seriously! But try hiring a local chef to come in your villa and cook for you. It’s entertaining, informative, and, needless to say, delicious. Chefs who offer this type of service generally provide a range of menu options, allowing you and your family to craft just the perfect meal for a memorable night of dining. Our choice was Chef Mattisse, a traveling chef who strictly crafts private meals from his arsenal of time-tested and seasonal Italian recipes. You’ll be surprised at how far he’ll travel to spend an evening with you and share his cooking and his stories. Be sure to ask for a large helping of both.
If you’re interested in getting your hands dirty in a family kitchen and potentially taking a few culinary skills home with you, a cooking class in a local restaurant is an fun and interactive way to get kids involved in seeing some of their favorite foods come to life. In the village of Greve in Chianti, Pizzeria La Cantina offers classes taught by the family’s matriarch. You’ll be treated to the family’s culinary secrets, as well as its own vintages that each bear the name of a family member.
Jason Bacon is a travel-addicted Creative Director in Portland, Oregon and wanders regularly with his wife and their three adventurous kids. They love challenging each other to eat the odd, unknown, and unexpected foods during their travels. His 17-year old daughter is hands down in the lead.
This writer received a complimentary tour for the purpose of this review. However, all opinions expressed are solely his own.