Self-drive day-trips

Spend a day winding through the sun-drenched hills of Chianti Classico, where Campo Sasso is also located, the heart of Tuscany’s wine country. Start from the North-eastern corner of the region from Campo Sasso and head towards Greve in Chianti. You’ll see the amazing patchwork of vineyards, olive groves, and medieval castles. You can visit historic wineries to taste the iconic Sangiovese-based wines, paired with local pecorino cheese and cured meats. We recommend booking if you want to tour the cellars. Stop in the towns of Castellina, Radda and Panzano for a stroll through cobbled streets, artisan shops, and rustic eateries. A day dedicated to discovery is what it’s all about. Our favorite stops for delicious food are Dario Cecchini in Panzano (for amazing meat dishes), and Ristoro di Lamole which not only is scrumptious but also offers breathtaking views. Make sure to call ahead of time to reserve a table!

Experience a day trip to Florence from Campo Sasso, only half an hour away by car, diving into the art, architecture, and energy of the Renaissance capital. Park near the Piazza Poggi (paid street parking) and head to the iconic Duomo and admire its grandeur. Stroll through Piazza della Signoria and see the copy of Michelangelo’s David (the original is at the Accademia Gallery and you will need to purchase tickets in advance). You can tour the Palazzo Vecchio which is amazing, with views from the top. Cross the historic Ponte Vecchio for jewelry shopping and river views, then explore the artisan district of Oltrarno. This is the side that Formaggioteca Terroir is on, in the San Niccolò neighbourhood. Enjoy a leisurely lunch or aperitivo at a rooftop bar overlooking the Arno, or head for the central market where food stalls are open all day long (top floor), stop by our cheese & wine bar, or check out one of our other favorites like Le Volpi e l’Uva. If you’re staying for dinner, a fun place is Santo Bevitore, and for a more intimate dinner try Osteria dell’Enoteca or Osteria Oltrarno, both safeguarders of the local Slow Food movement. Florence offers a perfect blend of culture, beauty, and charm — all just a short drive from the Tuscan countryside.

Set out from Podere Campo Sasso for a scenic drive into the heart of Val d'Orcia, a UNESCO World Heritage landscape of rolling hills, cypress-lined roads, and golden wheat fields. Begin your day in Montepulciano, and its steep cobblestoned streets. Reaching the top you’ll find several winery cellars on the way, visit De Ricci’s unique underground cellars (best book your tasting in advance), and browse the lovely shops on the way. Pienza is the “ideal Renaissance city,” where narrow lanes lead to stunning views and shops selling pecorino cheese and local honey. Then continue to Bagno Vignoni, a tiny spa village famous for its ancient thermal pool right in the main square. Enjoy a gelato while you stroll around the hot water springs. Wrap up your journey in Montalcino, home of the world-renowned Brunello wine — perfect for a tasting overlooking the vineyards. Peaceful, poetic, and full of sensory delights, Val d’Orcia is Tuscany at its most iconic. For foodies, check out the Podere il Casale (cheese farm & restaurant) just outside Pienza, or Locanda Demetra just outside Montalcino - both have excellent food & views, but make sure to book before going!

Set out from Podere Campo Sasso and head first to Monteriggioni, a storybook hilltop village encircled by perfectly preserved medieval walls. Stroll along the ramparts for sweeping countryside views, grab a coffee in the peaceful main square, and soak in the atmosphere of a place that hasn’t changed much in centuries. Then continue to Siena, just 20 minutes away, where Gothic elegance meets lively street life. Wander the narrow lanes to the breathtaking Piazza del Campo, home of the famous Palio horse race, and don’t miss the ornate Duomo, a masterpiece of marble and mosaic. With its rich history, warm brick facades, and vibrant local cuisine, Siena offers an unforgettable dive into the cultural soul of Tuscany — all within easy reach of your countryside base.

From Podere Campo Sasso, enjoy a relaxed drive through vineyard-covered hills to the medieval marvel of San Gimignano. Known as the “Manhattan of the Middle Ages” for its soaring stone towers, this walled town is perfect for exploring on foot. Climb the Torre Grossa for panoramic views, browse artisan shops, and treat yourself to a scoop (or two) of award-winning gelato in Piazza della Cisterna. In the afternoon, head just 20 minutes down the road to Colle Val d’Elsa, a quieter gem often overlooked by crowds. This historic town is famed for its crystal glass production — visit a local workshop or the Crystal Museum for a glimpse into the craft. Take a leisurely walk through the elevated old town, lined with stone archways and peaceful piazzas, before returning home through classic Tuscan countryside. In Colle Val d’Elsa you’ve got Bis Osteria restaurant which is one of our favorites, or you can splurge and go to 2 star Michelin Arnolfo. If you’re up for a longer day, you can substitute Colle Val d’Elsa with Volterra, which is a fascinating town for it’s Etruscan museum and medieval cobble-stoned streets. It’s a little further out, but the views are stunning and you can discover the locally made Alabaster.

Take a day trip from Campo Sasso to Arezzo, a beautiful Tuscan city rich in history, art, and atmosphere. Stroll through Piazza Grande, visit the Church of San Francesco with its famous fresco cycle by Piero della Francesca, and browse artisan shops along the medieval streets. If you’re visiting on the first weekend of the month, don’t miss the renowned Antiques Fair filling the piazzas with vintage treasures. After lunch, head to one of the nearby villages — Lucignano, a perfectly preserved walled town with spiral streets, or Anghiari, known for its stone houses, artisan workshops, and sweeping valley views. Both offer an authentic, peaceful slice of Tuscany. You can also combine Arezzo with Cortona, but of course, get going early so you have time to enjoy both towns to the most!