Mention Tuscany and many people will think of the famous book/movie “Under the Tuscan Sun”. The reality, though, is that the romantic “hot spots” of Tuscany can be thrumming with masses of tourists at every turn; dodging selfie-sticks and bumping fanny-packs is not as sexy as it sounds.
But there’s hope yet to have that perfect romantic Tuscan getaway – you just have to know where to look. Luckily for you, we’ve already done the looking. We specialize in travel that is authentic, immersive, and memorable, exploring the beautiful back roads and charming small towns of Italy. You can find all the delectable food and the heart-thumping vistas that everyone raves about in the Val d’Orcia of southern Tuscany.
We start in the medieval walled town of San Quirico d’Orcia, a well-preserved medieval walled town that was the filming location of a 1954 Romeo and Juliet film. San Quirico has limitless charms and little-known architectural interests; a day or three can easily be spent just wandering the streets and the elegant, extensive (and free) town garden. Stay at the beautiful 12th-century lodging of Casa Lemmi, right on the town square. Bells will chime through your window from the Collegiate Church across the tiny square. The thing that sets this hotel apart from other lodgings, though, is the “Magic Bath”: A Roman-style salt bath built on an ancient subterranean structure. Book an hour of private relaxation before heading out to explore the Val d’Orcia …or before heading back upstairs, depending on how the bath goes…
A scant 10-minute drive out of San Quirico is the even tinier spa town of Bagno Vignoni. Bagno means “bath”, and the place is aptly named: The entire central piazza (town square) is a thermal pool. Swimming in the square is not allowed, but many of the hotels in town have upscale hot-spring spas. Walking the little streets here, you’ll feel like the stars of a Fellini movie.
A 25-minute drive from San Quirico is perhaps the most famous of all Tuscan vistas: The winding, cypress tree-lined road that graces every Tuscany guide and Italian coffee-table book. This is the Strada di Valoresi, where you can take your own Pulitzer-worthy selfie. (Note: Driving up this road itself is not recommended, as it is a rocky dirt track; the only view it offers is of pieces of your undercarriage in the rearview mirror, which will test even the most committed relationship!)
Not far from this famous sight, over the farmlands, olive groves, and vineyards, is another walled hill-town, Monticchiello. A stroll through this medieval village is a walk back into time, yet it’s so small as to take no time at all. Just inside the Porta Sant’Agata (the main town gate), look for Osteria La Porta. On their beautiful patio overlooking the countryside, you can dine on classic Tuscan cuisine prepared with great expertise – succulent roasted meats, perfectly handmade pastas, tantalizing desserts. Arrive hungry, and eat and drink to your hearts’ content. The osteria also offers rooms and apartments for rent in the town.
One of our very favorite drives in all of Tuscany is the road from San Quirico to Pienza. Though the drive should be a mere 15 minutes, we’ve never managed to make it in less than 30, usually much longer. Why? We feel constantly compelled to stop and take pictures of this stunning landscape, and so will you. In particular, look to the south for a lonely little chapel across the rolling fields – this is the Capella di Vitaleta, an iconic Tuscan sight (rivaling the fame of the Strada Valoresi) that for centuries has inspired people to notions of love. You may see newlywed couples posing in this field, walking through the tall grasses, sitting on the hay-bales, or possibly even standing at the chapel itself, having found the elusive route to the place.
Pienza itself, another Romeo and Juliet filming location (in this case the 1968 Zeffirelli version), is the quintessential Tuscan hill-town. Its walls are permeated by the aroma of the famous and delicious cheese, pecorino di Pienza, creating a constant reminder of the delectable food that can be found in any number of lovely restaurants here. Our favorite of these is the little Trattoria da Fiorella: Run by two brothers, the restaurant serves traditional dishes in a relaxed, cozy atmosphere. The walls are adorned with art by the wife of one of the brothers.
Speaking of art: Just around another corner, you’ll find the studio of ceramic artist Linda Bai. Linda’s work is beautiful, often painted with Tuscany-inspired scenes; her studio is like a museum, and her back room extends into an ancient cave in the hillside. This is an excellent place to pick up a keepsake to help you remember your trip for years to come, whether it’s a little wine stopper or a larger and more ornate piece. You can even order a personalized work in advance, as we did.
Pienza’s southern wall creates a “balcony” that commands a sweeping view of the entire Val d’Orcia and Monte Amiata. It is practically impossible to walk these streets and not take someone by the hand or walk arm in arm, so make sure you don’t leave your loved one alone for a solo walk here. In fact, one of the little streets leading to the balcony is called Via dell’Amore, and for good reason. Sunsets here, especially, will render you awe-struck and love-struck.
These sights, towns, and restaurants listed here are just a few of our many favorite places in this lovely and quiet region of Tuscany. We’ve sent many a happy couple to these and other fairy-tale locations in Tuscany and throughout Italy. When couples focus on immersing themselves into unique experiences rather than the typical “to-do” travel checklists, they come back relaxed, inspired, and with romantic memories that will last their whole lifetime together.
Zeneba Bowers and Matt Walker, owners of LittleRoadsEurope.com, are the authors of two foodie guidebooks to back-roads Italy, including a Tuscany guide. They create customized, off-the-beaten-track driving itineraries for clients wanting to have authentic, immersive, affordable, and memorable travel experiences. When they aren’t traveling, Zeneba and Matt are professional classical musicians in the Grammy-nominated Alias Chamber Ensemble and in the Nashville Symphony.