I know a lot of you are here because you have already booked trips to Tuscany. I have never been successful in dissuading people from visiting the 20th most interesting region in Italy and I know I'm not going to change your mind, but I'd like to plant the seed that there are other places in Italy that require attention and support. Maybe you can visit one of them on your next (or this!) trip!

For the few of you who are just researching and haven't landed on a destination, may I suggest going literally anywhere else in Italy? Have you heard of Molise? It's magic. What about Sardinia? There's nothing better. (You can read more about it in my Italian Islands guide here.) I'm certainly not going to deny the value of the people doing interesting and delicious things in Tuscany, but let's just all agree that there are other places in Italy worth your time and support (and that are less burdened by overtourism). Either way, here are some tips for visiting the part of Tuscany that is most frequented by travelers, such as the Val d’Orcia and surrounding areas.

Wineries, Restaurants, and Sites: 

• Sesti Vineyard, near Montalcino: It’s a whole fascinating lunar-calendar-based vineyard. Very cool place.
• Pacina: A family-run winery close to Siena, with lovely, homey apartment-style accommodations on-site and occasional cheffy events. 
• Abbazia di Monte Oliveto Maggiore: This almost monumental complex is a gorgeous monastery founded in the 1300s on a remote hillside in the heart of the Val d’Orcia. It’s one of those places that when visiting it feels a little bit like stepping back in time, plus you get the ideal hybrid of activities between outdoor time in nature combined with stellar art history lessons. Besides the abbey church, you can tour yourself around the woodland paths and the chapels sprinkled throughout; the abbey cloister, whose walls are completely covered with amazingly well preserved Renaissance frescoes, on a par with many of their contemporary examples but far less visited; the monastic library and refectory; and the shop full of everything the modern monks make on site, from honey and jams to wine and spirits. There’s also a small restaurant on the property that serves typical Tuscan fare, but you can also pop into the surrounding towns for great dining options (see the list below). 
• La Foce: Further south, this super beautiful estate has a great restaurant called Dopolavoro, which serves traditional Tuscan dishes. The estate also has gardens that you can explore (with ticketed reservations) and nice accommodations if you can’t bear the thought of not staying the night.   

Towns, Villages, and Other Areas to Explore: 

• Bagno Vignoni: A small village known for its thermal springs (there’s even water in the center of town). For thousands of years, the waters have attracted visitors for their healing qualities and they bring a sort of beautiful haunted tranquility to the zone. I love eating lunch at Osteria del Leone (Via Dei Mulini). There’s a sort of wacky archeological park in Bagno Vignoni, too, called Parco dei Mulini. Worth a peek if it’s not too hot. 
• San Quirico d’Orcia: After BV, I like popping into the town of San Quirico d’Orcia for a coffee and a stroll. It’s an absolutely stunning village founded in Etruscan times and populated by late medieval/Renaissance churches, palaces, and gardens. You can get great artisanal gelato at Golosi di Gelato 2.0 in the center (in Via Dante Alighieri), which also runs a location in Siena. 
• Pienza: Planned as an “ideal city” by Alberti and embellished by Pope Pius II, Pienza is absolutely gorgeous. La Bandita Townhouse is great for lunch and the gelato at Buon Gusto is probably the best gelato in Tuscany. Check out the Cathedral and the numerous luxurious palaces (thanks to abundant papal patronage) that put this tiny place on the map. 
• Via Francigena: This ancient pilgrimage route, which still today attracts hikers and travelers, connects Rome with Canterbury (England!), and a stretch of it cuts through the Val d’Orcia, the sub-region of Tuscany you are (hopefully) staying in. Pack a lunch and hit the trails for sweeping views over vineyards, medieval villages, and cypress groves. This site can key you into difficulty levels and possible itineraries (doing the whole thing is a bit ambitious, but a small part is doable if you make sure to pack plenty of water and snacks, just like any hike).

Siena

• Restaurants and wine bars worthy of meals: Check out Salefino for the most modern, creative food in town (and for natural, organic wines from all of Italy). The (heavily non-Tuscan) menu changes almost monthly and is particularly good in the summer, when it’s too hot to eat most traditional local fare. Do spend some time at their wine bar, the Bottiglieria Salefino just across the piazza, either before dinner at the restaurant or instead of--the tapas-style plates (often featuring seafood from the Tuscan coast, a rare find here) can easily be made into a meal. So can the more traditional but nice rotating plates at Vineria Tirabusciò, a cozy wine bar more in the immediate center with more stellar natural wines and craft beers.
• For great traditional senese food, however, the best spots are Osteria del Gatto (Via San Marco 8) and Ristorante/Pizzeria all’Orto dei Pecci (in a medieval-garden-turned park, down the hill from the Campo). Wherever you go, make sure to get pici, Siena’s favorite pasta shape, at least once. Many guidebooks and/or travelers not on a budget will direct you to Osteria Le Logge, the Michelin-listed fine-dining establishment behind the Campo. It is good, and not as expensive as it could be, but you can eat just as well if not better (and more like a local) at these other places. 
• Pastries and Coffee, Gelato, and Drinks: For morning pastries, go to Nannini for Siena’s traditional ricciarelli and cavallucci cookies, which also make appearances as gelato flavors in the warmer months. For gelato, even better to go to Golosi di Gelato (inside the Bar Bonucci). Il Battistero is the best place for specialty coffee (the Caffetteria side is open from the early morning), and being nestled under the Baptistery of the Duomo alongside the same group’s bistro/enoteca makes it a great place to spend any time of day. Do aperitivo there, or find even more craft cocktails at Trefilari. If you want a drink in the Campo, know that the drinks themselves aren’t anything special, but since they’re not necessarily overpriced it is fun to do (just skip the food in the Campo for sure).  
• Where to stay: Battistero’s boutique hotel in the same piazza is lovely, or if you want to immerse yourself in the countryside while still enjoying Siena’s center for several days, you can post up outside the city at Tenuta di Spannocchia, a traditional agriturismo about 30 minutes away with villa-type bedrooms and individual house rentals. Spannocchia offers tours and tastings of their wine cellar, vegetable gardens, and the locally revered Cinta Senese pigs (with house-made pork products to try afterward); as well as family-style farm dinners. 
• Sights: Beyond the Palazzo Pubblico and Duomo (both of which you should certainly still go to, for the interiors), check out Santa Maria della Scala, the Museo dell’Acqua for a cool and interactive look at the medieval aqueduct system (which you can tour separately), and the Synagogue and Jewish Museum. Each of Siena’s contrade--the small neighborhood districts that most famously race against each other in the yearly Palio horse race--has its own museum, too, displaying historical artifacts and Palio costumes with a healthy dose of local lore. Opening times vary (both between the museums and generally throughout the year), and some contrada museums are more active than others, but in the summer it’s a good bet that more of them will be open for the Palio season. You can find more info on the individual museums here.

Other Parts of Tuscany

• Lunigiana: This mountainous region in northern Tuscany close to the borders of Liguria and Emilia-Romagna is all about castles, medieval walled villages, and fortresses (in the Middle Ages, land near the sea was always in need of defense). Author and lifestyle guru Annette Joseph turned one such medieval fortress into her own property, La Fortezza, a “monastic chic” B&B-meets-private-retreat-property. You can use La Fortezza as a base to explore this under-explored region and its very cool medieval towns tucked into the dramatic mountainsides.
• Isola di Giglio: The food scene on this island is tough, but I like staying at Pardini’s Hermitage (a special family-run guest house, reachable only by boat) and drinking wines from the Altura winery by Francesco Carafagna, the best winemaker on Giglio IMO.