Begin in Florence, but resist trying to see everything — this city rewards depth over breadth. Book the Uffizi or Accademia (David) months in advance and focus on one major museum per day. Walk across the Ponte Vecchio at sunset, climb the Duomo's 463 steps for a 360-degree view of terracotta rooftops and the Tuscan hills beyond, and explore the Oltrarno neighborhood on the south bank — artisan workshops, the Palazzo Pitti gardens, and the best trattorias in the city.
For food, avoid anything near the Duomo with photos on the menu. Instead, find Trattoria Mario (shared tables, no reservations, cash only, closed at 2:30 PM sharp) for ribollita and bistecca, or All'Antico Vinaio for the sandwich that regularly has a queue down the street — it's worth the wait. End the evening in the Piazzale Michelangelo as the city lights come on beneath you.
Driving tip: Do NOT drive into Florence's city center. The ZTL (restricted traffic zone) will automatically photograph your license plate and fine you €100+ per violation. Park at the Villa Costanza park-and-ride and take the tram. Pick up your rental car when you're ready to leave the city.
Stay: Hotel Davanzati (central, excellent breakfast) or Palazzo Guadagni (Oltrarno, with a terrace overlooking Santo Spirito).
Pick up your rental car and drive the SR222 (Chiantigiana), the classic road through Chianti wine country. This is the Tuscany of postcards — rolling hills striped with vineyards and olive groves, cypress-lined driveways leading to stone farmhouses, and medieval villages perched on hilltops.
Stop at Greve in Chianti, the region's unofficial capital, where the triangular Piazza Matteotti hosts a Saturday market. Visit the Antica Macelleria Falorni, a butcher shop since 1729, for wild boar salami and finocchiona (fennel-studded salami). Continue to Castellina in Chianti for wine tasting — Chianti Classico (marked by the black rooster logo) ranges from light and cherry-fruited to structured and age-worthy. Fonterutoli and Castello di Volpaia are among the best estates for visits.
Arrive in Siena in the late afternoon. The shell-shaped Piazza del Campo is Italy's most beautiful square — sit on the sloping brick surface with a gelato and watch the evening passeggiata. The Duomo, with its black-and-white striped marble, is overwhelming in its detail — Nicola Pisano's pulpit, the Piccolomini Library frescoes, and the inlaid marble floor (uncovered only in August-October) are all masterpieces.
Stay: Palazzo Ravizza (quiet garden, city views) or Campo Regio Relais (terrace overlooking the Campo).
Drive west to San Gimignano, the "Medieval Manhattan" — a hilltop town famous for its 14 surviving medieval towers (originally 72) that pierce the skyline like a stone cityscape. The town is touristy but genuinely stunning. Climb the Torre Grossa (the tallest tower, inside the Palazzo Comunale) for views over the towers and the Val d'Elsa. Buy the world's best gelato at Gelateria Dondoli on the main square — multiple-time world champion gelato maker Sergio Dondoli creates flavors like Crema di Santa Fina (saffron cream) and Vernaccia sorbet.
Continue to Volterra, a less-visited hilltop town with 3,000 years of history stacked up in its streets. Etruscan walls, a Roman theater (still being excavated), medieval palaces, and alabaster workshops coexist in a town that feels authentically lived-in rather than preserved for tourists. The Etruscan Museum (Museo Guarnacci) has one of Italy's best collections of Etruscan artifacts, including the hauntingly elongated bronze figure "Shadow of the Evening."
Eat: L'Incontro in Volterra for handmade pici pasta with wild boar ragù — the quintessential Tuscan dish.
Stay: Hotel La Locanda in Volterra or Foresteria di San Gimignano.
Drive south into the Val d'Orcia, a UNESCO World Heritage landscape and the most photographed corner of Tuscany. The rolling clay hills (crete senesi), lone cypress trees, and golden light have inspired artists from Renaissance painters to Instagram photographers.
Base yourself in or near Pienza, a town redesigned in the 15th century by Pope Pius II as an "ideal Renaissance city." The main street, Corso Rossellino, is lined with shops selling pecorino cheese — Pienza's pecorino is considered Tuscany's finest. Walk to the edge of town for views across the Val d'Orcia that will stop you in your tracks.
Day-trip to Montalcino, home of Brunello di Montalcino, one of Italy's greatest wines. Visit the Fortezza for wine tasting (you can sample several Brunellos by the glass), then drive south to the Abbazia di Sant'Antimo, a Romanesque abbey in an olive grove where monks still chant Gregorian plainsong. Drive the famous cypress-lined road near Monticchiello — the winding row of cypresses against the green hills is Tuscany's most iconic image.
Soak in the free hot springs at Bagno Vignoni, a village whose main square is literally a thermal pool (you can't swim in the square pool, but the Parco dei Mulini below has free natural hot spring pools in the river gorge). Alternatively, the Terme di Saturnia further south has a cascade of natural hot pools open 24/7 and free to all.
Stay: La Bandita Townhouse (Pienza) or Agriturismo Il Rigo (working farm with Val d'Orcia views).
Visit Montepulciano, another hilltop wine town, this one producing Vino Nobile di Montepulciano. The steep main street (Corso) climbs to the Piazza Grande, where the Palazzo Comunale's tower offers 360-degree views. The underground Cantina de' Ricci occupies medieval and Etruscan cellars beneath the town — a wine tasting in these vaulted stone chambers is atmospheric and affordable.
Drive north through Cortona (if you've read "Under the Tuscan Sun"), an Etruscan hilltop town overlooking the Val di Chiana and Lake Trasimeno. The steep streets, Medici fortress, and Diocesan Museum (with two Fra Angelico paintings) make it worth a stop. Continue to Arezzo for the Piero della Francesca frescoes in the Basilica di San Francesco — one of the supreme achievements of Renaissance painting, recently restored to glowing color.
Return to Florence via the A1 autostrada (1 hour) or meander through the Pratomagno hills on smaller roads. Drop off the rental car at Florence Airport or the city-edge rental offices.
Driving tip: Tuscan hill towns are usually car-free in their centers. Park in the lots outside the walls (often free or €1-2/hour) and walk in. Roads between towns are well-maintained but winding — allow more time than GPS estimates. The famous white gravel roads (strade bianche) of the Val d'Orcia are navigable in a regular car if you drive slowly, but check with your rental company about gravel road coverage.
For multi-country trips, pick up and return the car in the same country to avoid expensive one-way drop-off fees (often €200-500).
| Item | Estimated Cost |
|---|---|
| Rental car (7 days, compact) | €200-350 |
| Fuel (petrol, 500 km) | €65-90 |
| Tolls (autostrada sections) | €15-25 |
| Accommodation (6 nights mid-range) | €500-900 |
| Food (meals for 2 people) | €400-650 |
| Activities (museums, wine tastings, Duomo climb) | €80-140 |
| Parking fees | €20-40 |
Country-by-country driving requirements, packing list, and emergency contacts — all in one PDF.
Rental companies in italy charge $15-30/day for excess reduction at the desk. Standalone policies cover the same thing for a fraction of the cost — and you can buy before you go.
Reduce your excess to zero from $49/trip
Save up to 70% vs rental desk insurance
These policies reimburse you if the rental company charges your card for damage. They do not replace the rental company's basic insurance (CDW/TP) which is always included.
Compare car rental prices for this route.
Country-by-country driving requirements, packing list, and emergency contacts — all in one PDF.
Free. No spam. Unsubscribe anytime.