The Best of Tuscany Drive

Arrival in the Cradle of the Renaissance

Collect your rental car at Florence Airport and check in to your hilltop hotel above the city. Spend the afternoon walking the Oltrarno neighbourhood — craft workshops, artisan leather, and hidden piazzas.

What’s Included:
Your program features carefully selected accommodations with daily breakfast and curated guided excursions as outlined in the itinerary.

As this is a self-drive journey, car rental is tailored to your preferred vehicle category and travel dates and is added to the final package price upon confirmation.

You may also enhance your experience with optional add-on activities and private local guide services available throughout your trip.

Chianti Roads to Etruscan Heights

Travel from Florence into the wilder, more contemplative landscapes of southern Tuscany, following one of the region’s most iconic scenic routes toward an ancient hilltop town steeped in Etruscan heritage.

Route tip: Leave Florence heading south on the SR222 — the famous Chiantigiana road — winding through vineyards and cypress avenues into the heart of Chianti Classico country. Depart Florence by 9am to catch the soft morning light on the hills and reach Greve before the day-trippers arrive.

Scenic stops en route:

• Greve in Chianti (~30 min south of Florence on SR222) - The informal capital of Chianti Classico, Greve is built around a triangular porticoed piazza unlike any other in Tuscany — asymmetric, slightly sloping, ringed by covered arcades housing wine shops, butchers, and cafés. A statue of Giovanni da Verrazzano, the explorer who first mapped New York harbour, stands at its centre.
  Insider tip: The road south of Greve through Panzano — a short detour — passes the butcher shop of Dario Cecchini, a legendary figure who recites Dante while he works. Worth a stop if open.
• Castellina in Chianti (~55 min from Florence) - A compact, well-preserved hilltop town with an unexpected secret: the Via delle Volte, a covered Etruscan-era passage running beneath the town walls, its arched openings framing views across the valley below like a series of picture windows. The 15th-century Rocca fortress at the centre was built by Lorenzo de' Medici.
  Best for: A 30-minute walk. Enter the Via delle Volte from the north end of the main street and walk its length — the interplay of shadow and light, and the sudden valley views through each arch, is one of the quiet architectural pleasures of the Chianti. Several excellent wine shops occupy the old vaulted cellars below street level.

From Chianti, the route gradually leaves the vineyard-dominated landscape behind, transitioning into the more rugged and open terrain of inland Tuscany as you approach Volterra.

Driving distance: 110 km
Estimated time: approx. 1.5 hours (excluding scenic stops)

Arrival in Volterra

Arrive in Volterra, one of Tuscany’s most atmospheric towns, dramatically set atop a windswept plateau. With origins dating back to the Etruscans, Volterra retains a distinctly austere beauty, with well-preserved medieval walls, notable Roman remains, and a historic center of honey-colored stone.

After checking in to your countryside retreat overlooking the rolling hills, take time to relax and absorb the quiet, evocative setting.

Medieval Siena — The Gothic Republic

After breakfast and check-out, depart Volterra and begin your journey southeast through the ever-changing Tuscan landscape.

Route tip: Head northeast from Volterra on the SP68, then drop south through Colle di Val d'Elsa and onto the SR2 Cassia. This route passes through classic rolling Tuscan countryside — wheat fields, cypress avenues, and medieval hill towns. Best driven in morning light when the mist sits in the valleys.

Scenic stops en route:

• Colle di Val d'Elsa (~30 min from Volterra) - Often overlooked in favour of San Gimignano, Colle di Val d'Elsa divides into two distinct parts: the modern lower town and the Colle Alta — a long, narrow ridge of medieval streets accessible through a stone gateway. The upper town was the birthplace of Arnolfo di Cambio, the architect of Florence's Duomo and Palazzo Vecchio.
  Best for: A 30-minute walk along the single ridge road, the 13th-century cathedral, and an espresso with a view over the valley. Colle is also the crystal glass capital of Italy — the main street has several artisan workshops open to visitors.
• Monteriggioni (~50 min from Volterra) - One of the most perfectly preserved medieval fortifications in all of Tuscany. Monteriggioni is an entire village enclosed within a circular ring of walls with 14 towers — built by Siena in 1213 as a defensive outpost against Florence. Dante used it as a metaphor for the giants guarding Hell in the Inferno.
  Practical note: There is a small paid car park just outside the walls. The village gets crowded by midday in summer — arrive early or late.

After your leisurely journey, arrive in Siena, where medieval streets and the stunning Piazza del Campo await.

Driving distance: 100 km
Estimated time: approx. 1.5 hour (excluding scenic stops)

Arrival in Siena
Arrive in Siena, the jewel of Tuscany’s rolling hills. After checking in to your hotel, take some time to soak in the city’s medieval charm. Wander through the winding streets of the historic center, where brick alleys lead to bustling piazzas and the majestic Siena Cathedral rises above the skyline. For a deeper experience, consider joining a guided city tour to discover the stories behind the Piazza del Campo, the Torre del Mangia, and the city’s famed Palio tradition. Alternatively, enjoy a leisurely stroll with a gelato in hand, stopping at a local café to watch the city’s rhythm unfold around you.

Into the Val d'Orcia — A UNESCO Landscape
In the morning, after breakfast and check-out, you will begin your scenic drive from Siena toward the heart of the Val d’Orcia, transforming the journey into a relaxed exploration of Tuscany’s most iconic landscapes.

Route tip: Head southeast from Siena on the SR2 Cassia, then cut east through the bare clay hills of the Crete Senesi — the most otherworldly landscape in Tuscany. Rolling badlands of pale grey soil, lone farmhouses on ridgelines, and the famous cypress-lined avenue of Poggio Covoni. Morning light turns the clay luminous; depart by 9am.

Scenic stops en route:

• Buonconvento (~25 min from Siena on SR2) - Buonconvento sits at the confluence of the Arbia and Ombrone rivers, its perfectly intact medieval brick walls rising straight from the valley floor with no suburban sprawl around them.
  The cypress moment: Just south of Buonconvento on the SR2, the road crests a low hill and the full spectacle of the Crete opens up — rolling grey-clay domes stretching to the horizon, each ridgeline crowned with a tight group of cypresses. Pull over. This is the image.
• Asciano & the Crete Senesi viewpoints (~40 min from Siena) - The road from Buonconvento to Asciano crosses the most photogenic stretch of the Crete Senesi. The landscape here is unlike anything else in Tuscany — smooth, rounded clay mounds called biancane, almost entirely bare of vegetation, broken only by lone farmhouses on ridges and the characteristic dark clusters of cypress that Sienese farmers planted for centuries as windbreaks and property markers. In morning mist or raking autumn light the scene looks painted.
  The cypress clusters: The most celebrated groupings are not signposted — they are simply there, visible from the road. The cluster near Poggio Covoni, on a low hill northeast of Asciano, is one of the most recognisable. Further south, the lonely farmhouse of Baccoleno — a single building at the end of a long cypress-lined track on an empty ridgeline — is the single most photographed spot in the entire Crete Senesi. The lane to Baccoleno branches from the SP438; the view is best from the road, not up close.
• Abbazia di Monte Oliveto Maggiore (~1.5 hrs from Siena) -A great Benedictine monastery hidden in a dense forest of cypress and holm oak — a striking contrast to the bare hills outside. The approach lane through the forest, with the red-brick tower appearing suddenly through the trees, is an arrival to remember.
  Don't miss: The Great Cloister, whose walls carry a breathtaking cycle of 36 frescoes of the life of St Benedict by Luca Signorelli and Il Sodoma, painted between 1497 and 1508. Il Sodoma included a self-portrait with his pet badgers in panel nine. The monks produce honey, herbal liqueurs, and olive oil sold at the abbey shop — the elisir digestivo is worth taking home.

The drive concludes along the SP146 — arguably the most photographed road in Italy — a straight avenue of centuries-old cypresses in disciplined double rows cutting across the Val d'Orcia floor, with Monte Amiata on the horizon. The road leads the eye directly to Montepulciano's ridge, where the town rises at 605 metres above a landscape of vineyards producing its renowned Vino Nobile.

Driving distance: approx. 95 km
Estimated time: approx. 1.5 hours (excluding scenic stops)

Arrival in Montepulciano
Upon reaching the rolling countryside near Montepulciano, check into your charming country hotel, peacefully set outside the town. Take some time to breathe in the fresh Tuscan air and settle into the tranquil surroundings.

Tuscan Hills to Medieval Towers
After a relaxed morning enjoying the peaceful rhythms of Montepulciano, you’ll check out and begin your scenic journey through the rolling Tuscan countryside toward the enchanting hilltop town of San Gimignano.

Route tip: Head northeast from Montepulciano into the Valdichiana, then swing northwest through Sinalunga and climb into the Crete Senesi via Rapolano Terme — a thermal spa town almost entirely off the tourist map. From there cross the SR2 and head north through the soft hills of the Arbia valley to Lucignano and Poggibonsi before the final push to San Gimignano.

Scenic stops en route:

• Sinalunga (~20 min northeast of Montepulciano) - A compact and genuinely local hilltop town on the eastern edge of the Crete Senesi, almost entirely bypassed by tourism despite sitting at the junction of two major Tuscan valleys. The old town of Sinalunga occupies a long narrow ridge with views across the Valdichiana to the east and the first clay hills of the Crete to the west — a double prospect that few hill towns can match.
  Best for: A brief 20–30 minute stop and morning coffee. The central Piazza Garibaldi has a good bar and a covered market on certain mornings. The Collegiata di San Martino contains a celebrated 15th-century Annunciation by Benvenuto di Giovanni — a minor but beautiful work in a church that sees almost no visitors.
• Rapolano Terme (~40 min from Montepulciano) - One of the least-known thermal spa towns in Tuscany, and all the better for it. Rapolano Terme sits on the northwestern edge of the Crete Senesi at the point where sulphurous geothermal springs emerge from the clay hills — the same geological forces that feed Bagno Vignoni to the south and the Larderello vents to the west. The two main spas, Terme Sensoriali and Antica Querciolaia, offer outdoor thermal pools open to day visitors surrounded by travertine terraces and Crete Senesi views.
  Why it works on this route: It offers a genuine thermal experience that is quieter and less visited than either Bagno Vignoni or the Saturnia pools, perfectly placed mid-morning when the light on the Crete is still low and warm. A 45-minute soak here before the drive north is a memorable interlude.
• Lucignano (~1 hr 10 min from Montepulciano) - One of the most architecturally unusual small towns in Tuscany. Lucignano is built on an oval hill in a series of four perfectly concentric elliptical rings of streets — like the growth rings of a tree, visible from the air or on any map. Walking inward from the outer ring toward the central piazza is a disorienting and delightful experience, every lane curving gently and never arriving where the eye expects.

Driving distance: 130 km
Estimated time: approx. 2 hours (excluding scenic stops)

Arrival in San Gimignano
Arrive in San Gimignano, the “Town of Fine Towers” rising gracefully above the Tuscan hills. After checking in to your country hotel, take some time to soak in the surrounding countryside, with its rolling vineyards, olive groves, and golden fields. Later, head into the village to absorb its medieval charm. Wander along narrow cobbled streets where stone buildings and artisan shops line your path, and the scent of fresh pastries and local wine drifts from cafés. Pause in the Piazza della Cisterna to watch life unfold in this sun-drenched square, or climb the Torre Grossa for sweeping views of the town and the surrounding Tuscan landscape.

Departure
As your unforgettable Tuscan journey comes to a close, savor one last morning in this enchanting region. After checking out from your hotel, embark on a scenic drive to the airport, passing the rolling hills and charming villages one final time.

Route tip: Head north from San Gimignano on the SP1 to Poggibonsi, then northwest on the Superstrada to Empoli before climbing the short hill road to Vinci — birthplace of Leonardo da Vinci, tucked into the olive-clad slopes of Montalbano above the Arno plain.

If time allows before your flight, consider the following scenic stops en route:

• San Miniato (~35 min northeast of San Gimignano) - Perched on three hills above the Arno valley, San Miniato was the Tuscan seat of the Holy Roman Emperors for centuries — Frederick II built a fortress tower here in the 13th century, of which the Torre di Federico II (rebuilt after wartime destruction) still dominates the skyline. The town commands a sweeping panorama across the Arno plain toward Florence on one side and the Valdelsa hills on the other, with San Gimignano's towers often visible in the distance on a clear morning.
  Don't miss: The view from the terrace below the tower at the top of the town — the full Arno valley spread below, Empoli's campanile visible in the plain, and on clear days the dome of Florence's Duomo on the horizon. A quietly magnificent send-off for the Tuscan hills.
• Vinci (~55 min from San Gimignano) - A small hill town on the southern slope of the Montalbano ridge, surrounded by olive groves and vineyards — and the place where Leonardo di ser Piero da Vinci was born on 15 April 1452. The Museo Leonardiano, spread across the medieval castle and an adjacent modern building, holds the world's largest collection of models built from Leonardo's drawings: flying machines, hydraulic devices, war engines, bridges, anatomical studies — all constructed to scale and operable where possible.
  Don't miss: The short drive or walk up to Anchiano, the hamlet 3 km above Vinci, where the farmhouse traditionally identified as Leonardo's birthplace still stands on a hillside of ancient olive trees. 

Driving distance: 75 km
Estimated time: Approx. 1 hour (excluding optional stop)