Curator’s statement
Tuscany is more than just a destination—it’s a living canvas where history, art, and nature blend seamlessly. From the golden hills of Val d’Orcia to medieval hilltop towns like Montepulciano and San Gimignano, every view looks like a painting and every street echoes with centuries. I explored this region both by bike and car—pedaling through vineyards, tasting olive oil under terracotta roofs, and watching sunsets fall over cypress-lined roads. This guide is based on that journey: a mix of scenic drives, cultural gems, and sensory experiences I hope will help you craft your own Tuscan story.
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Day 1: Val d’Orcia magic – Montepulciano, Pienza & Bagno Vignoni
Start: Rent a car from Florence or Chiusi train station and base yourself near Chianciano Terme (my cycling base, and a perfect hub).
Morning
Head to Montepulciano, perched on a ridge with dramatic views. Walk the medieval streets and visit Cantina Contucci or De' Ricci for atmospheric wine tastings inside ancient cellars. Try a glass of Vino Nobile di Montepulciano, a local treasure.
Lunch: At a wine estate just outside town, or a relaxed lunch at La Bottega del Nobile.
Afternoon
Drive (or bike!) to Pienza, the ideal Renaissance town envisioned by Pope Pius II. It's compact, walkable, and filled with pecorino shops and scenic terraces.
Evening
End the day in Bagno Vignoni, a spa village with ancient thermal springs in its central square. Stroll, soak, or simply relax.
Return to your base in Chianciano or nearby agriturismo.
A note from Sundar
Without a car: Buses are limited but possible via Chiusi or Montepulciano. Alternatively, consider a guided day tour from Siena.
Day 2: Rolling roads & olive groves – vineyard & olive oil day
Morning
Visit a vineyard in Val d'Orcia or Chianti. My favorites: Podere Il Casale (near Pienza, also makes cheese) and Tenuta Valdipiatta (Montepulciano).
Follow it with a stop at a frantoio (olive oil mill)—many offer tastings and show how cold-pressed oil is made.
Lunch: A long, scenic lunch at the vineyard—ideally with views.
Afternoon
Drive along the SR2 and SP146, two of Tuscany’s most iconic roads. Cypress trees, open fields, ancient farms, and sunflower patches await.
Evening
Dinner at a countryside trattoria or enjoy a homemade meal at your agriturismo.
Day 3: Siena – Gothic splendor & Palio passion
Morning
Arrive early and park outside the Siena historic center.
Visit the jaw-dropping Duomo and Piccolomini Library—striped marble and Renaissance frescoes at their finest.
Wander Piazza del Campo, home of the Palio horse race. Climb Torre del Mangia if you're up for it.
Lunch at a trattoria off Via di Città— quieter, more local.
Afternoon
Visit Santa Caterina's sanctuary, or enjoy views from Museo dell’Opera.
Evening
Stay overnight in Siena, or drive to San Gimignano to overnight nearby.
A note from Sundar
Without a car: Siena is accessible by bus or train from Florence and other towns.
Day 4: San Gimignano & Volterra – towers & stone
Morning
Arrive early in San Gimignano, famed for its medieval towers. Climb Torre Grossa, taste saffron gelato at Gelateria Dondoli, and peek into the Collegiata Church.
Lunch: Al fresco in San Gimignano or on the drive to Volterra.
Afternoon
Explore Volterra—a lesser-visited gem known for Etruscan ruins, alabaster shops, and dramatic scenery.
Optional: Visit the Roman Theater, Etruscan Gate, or Guarnacci Museum.
Evening
Return to Florence, Pisa, or wherever your journey continues.
A note from Sundar
Without a car: Transit between San Gimignano and Volterra is limited. A guided tour is ideal.
Need to know
Travel like I did: biking through Tuscany
On my first trip, I joined a guided cycling adventure arranged through one of our trusted Fora partners. We pedaled through Val d’Orcia, stopping in Montepulciano, Pienza, and Bagno Vignoni—with plenty of gelato breaks and cheese tastings along the way.
Be warned: every town is on a hill. The climbs are real—especially in summer. But if you’re active and up for the challenge, biking here is one of the most immersive ways to experience Tuscany.
Want to ride the same route? Message me and I’ll connect you with our expert partners for a guided or self-guided adventure tailored to your pace.
A scene straight out of "Gladiator"
While biking through Val d’Orcia, I came across a winding road framed by cypress trees—the kind you see in dreams. It turns out parts of "Gladiator" were filmed right here, just outside Pienza, near a farmhouse called Terrapille.
If you remember Maximus walking through golden fields toward home—that was Tuscany. And standing there in the breeze, surrounded by silence and soft light, it felt exactly like the movie.
Quick tips & summary
Rent a car or base in Siena/Montepulciano for flexibility
Watch for steep hilltop towns—wear good shoes!
Bike tours offer unmatched scenery (and effort!)
Don’t overplan—the best moments come unplanned
"Gladiator" fans: stop near Pienza for that famous cypress road
Eat slow, drive slower, and leave time for wine, cheese, and sky
Wine tasting & driving—plan smart
Italy’s DUI laws are strict, and rural roads can be dark and tricky. If you’re planning a wine day:
Appoint a designated driver
Join a guided tour
Hire a private driver for the day
Stay overnight at a vineyard agriturismo
Trust me, the wine tastes better when you don’t have to worry about getting back.
Planning a longer trip? This guide focuses on the Tuscan countryside, but it pairs beautifully with my companion guide to Florence. Whether you begin among vineyards and end with Renaissance masterpieces—or start in the city and roll into the hills—both journeys are designed to flow together seamlessly.
Travel Advisor
Sundar Rajan
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For more inspiration and insider recommendations, visit our Tuscany page.