Florence’s streets don’t just connect places — they connect centuries. The Via Romea Sanese, one of three official walking routes in Tuscany, starts at Piazza della Santissima Annunziata and winds south through medieval villages toward Siena, covering ground that Florentines once used as the shortest route to Rome. That kind of layering — Roman roads beneath Renaissance footfall — is what makes driving or walking here feel different from anywhere else. This article covers the historic routes that cross Tuscany, the practical realities of navigating them, and what to expect when you trade the autostrada for something slower.
The Via degli Dei (Way of the Gods) stretches 130 kilometres between Bologna and Florence, crossing the Apennines on paved roads, dirt tracks, and ancient Roman paths.
If you’re picturing a leisurely drive through rolling hills with a cappuccino at every stop, you’re not wrong — but you’re also not getting the full picture. Some of these routes involve unpaved sections, steep gradients, and limited services in smaller villages. Plan for actual driving time, not just distance.
Historic Routes Across Tuscany
Drivers who want scenic back roads
Hikers following pilgrimage paths
Cyclists tackling medium-difficulty terrain
Tuscany’s network of historic routes predates the modern highway system by centuries. The Via Romea Sanese — also called the Via Romea del Chianti — runs roughly 170 kilometres from Florence to Siena, alternating between paved back roads and dirt tracks. It intersects the official route of the Via Francigena in places, so you’ll occasionally share the road with pilgrims carrying shells and walking sticks. Four stages cross Florentine and Sienese territory, passing parish churches, abbeys, and villages like Sant’Andrea in Percussina, San Casciano in Val di Pesa, and Badia a Passignano.
The Way of St. Jacopo heads northwest from Florence toward Prato, Pistoia, Pescia, and Lucca, following the ancient Via Cassia-Clodia. It runs about 170 kilometres across six stages of easy to medium difficulty, and its historical importance comes from a relic of the Apostle James that arrived in Pistoia from Santiago de Compostela in 1145. For drivers, this route offers a quieter alternative to the A11 motorway, though some stretches narrow to single-lane country roads with stone walls on both sides.
Total length of the Way of Dante, a ring route linking Florence and Ravenna across 20 stages.
visittuscany.com
The Way of the Gods (Via degli Dei) connects Bologna with Fiesole, just north of Florence, covering 130 kilometres of paved roads, dirt paths, and Apennine crossings. Its name likely comes from mountain toponyms along the route — Mount Venus, Mount Adonis, and Mount Luario, linked to the Roman goddess Lua. The entire route is marked by CAI (Club Alpino Italiano) signs, making it navigable without a GPS if you’re paying attention. It takes four to six days on foot or two to three days by bike, depending on fitness level.
One honest limitation: these routes weren’t designed for modern cars. The Via Romea Sanese includes unpaved stretches that can be rough in a low-clearance rental. If you’re driving, a compact SUV rental gives you more flexibility on the dirt sections without being too large for narrow village streets. Michael and I learned this the hard way near San Donato in Poggio, where our sedan bottomed out on a gravel incline that looked fine on the map.
Main Experiences Along the Routes
Each route offers a different kind of encounter with Tuscany — some architectural, some culinary, some purely physical.
Florence’s Architectural Core
The San Lorenzo Church, with roots dating back to 393 AD, serves as the final resting place of the Medici family. It’s a logical starting point for any route heading south or west from Florence. The Duomo complex — Cathedral of Santa Maria del Fiore, with its white, green, and pink marble facade — dominates the skyline in a way that photos never quite capture. Brunelleschi’s dome required 463 steps to climb, and the view from the top stretches across terracotta rooftops to the Tuscan hills beyond. The San Giovanni Baptistery, with its massive bronze doors, sits directly across from the cathedral. Together, they form a trio that defines Renaissance Florence more than any single building could.
Villages and Vineyards on the Via Romea Sanese
Heading south from Florence, the Via Romea Sanese passes through Castellina in Chianti, one of the region’s most recognizable wine towns. The route touches Badia a Passignano, a Vallombrosian abbey surrounded by vineyards that produce some of the area’s most structured reds. If you’re driving, you can cover the Florence-to-Siena stretch in a long day, but the real value is in stopping. San Casciano in Val di Pesa has a small weekly market, and Sant’Andrea in Percussina is where Machiavelli wrote The Prince during his exile. The road surfaces vary — some sections are smooth asphalt, others are gravel farm tracks that require slower speeds.
On the Via Romea Sanese, fill up in Florence before heading south. Petrol stations become sparse after San Casciano, and the ones you find in smaller villages often close for chiusura between 12:30 and 3:30 p.m.
The Way of the Gods for Active Travellers
The Via degli Dei is the most physically demanding of the routes listed here, but it’s also the most rewarding for anyone who wants to earn their views. The Apennine crossings involve steady climbs, and the trail surface shifts between forest paths and old Roman paving stones that can be slippery after rain. Cyclists typically complete it in two to three days, while hikers budget four to six. The CAI markers are reliable, but carrying a waterproof hiking map of Tuscany adds a layer of security, especially in foggy conditions common in the higher elevations during spring and autumn.
Practical Planning for Driving and Walking
Timing, vehicle choice, and awareness of local restrictions make the difference between a smooth trip and a frustrating one.
| Route | Distance | Mode | Difficulty | Best Season |
|---|---|---|---|---|
| Via Romea Sanese | ~170 km | Walk or drive | Easy to moderate | April–June, September–October |
| Way of St. Jacopo | ~170 km | Walk or drive | Easy to medium | April–June, September–October |
| Way of the Gods | 130 km | Walk or bike | Medium | May–June, September |
| Way of Dante | 380+ km | Walk | Moderate to challenging | April–May, September–October |
Getting There and Getting Around
Florence’s historic centre is largely closed to non-resident traffic through ZTL (limited traffic zones). If you’re driving in, your hotel needs to be inside the ZTL and must register your license plate before you arrive — otherwise, cameras capture your entry and a fine arrives weeks later by mail. For the routes themselves, a rental car gives you flexibility, but consider the vehicle’s clearance. The unpaved sections of the Via Romea Sanese and the narrow lanes of the Way of St. Jacopo are manageable in a standard car if you drive slowly, but a compact SUV rental reduces the stress significantly.
Best Time to Travel
April through June and September through October offer the most reliable weather for both driving and walking. July and August bring heat that makes the Apennine climbs on the Via degli Dei genuinely unpleasant, and the same months see peak tourist crowds in Florence’s historic sites. The Way of Dante, at over 380 kilometres, is best attempted in spring or early autumn when daylight hours are longer and temperatures stay below 30°C. Winter rain can turn the dirt sections of the Via Romea Sanese into mud that’s difficult to drive through, and some mountain passes on the Way of the Gods may have snow into early April.
The ZTL in Florence operates daily, including weekends and public holidays. Even if you see other cars driving through the restricted zone, they likely have permits. Your rental car does not. Fines start around €80 and can arrive months after your trip.
Costs and Local Friction
Driving these routes costs more than you might expect. Toll roads in Italy add up quickly — the A1 between Florence and Bologna runs about €8 each way. Petrol prices in Italy typically sit 15–20% higher than in the US. Parking in Florence’s centre costs €25–€35 per day in garages, and street parking in the ZTL is not an option for non-residents. For walkers, the routes themselves are free, but accommodation in the smaller villages along the Via Romea Sanese and Way of St. Jacopo fills up during harvest season (September–October), so booking ahead is essential.
On the Ground: What to Know Before You Go
The practical details that don’t make it into the guidebooks but matter once you’re there.
Packing for Mixed Terrain
If you’re combining driving with short walks — which is the most common way travellers experience these routes — you need footwear that handles both. Cobblestones in Florence’s piazzas are slippery after rain, and the dirt paths on the Via Romea Sanese can be uneven. A pair of women’s walking shoes for Italy with good grip and a cushioned sole makes the transition from car to trail seamless. For longer hikes on the Via degli Dei or Way of Dante, proper hiking boots with ankle support are worth the weight in your luggage.
Food and Dining Along the Routes
Villages along the Via Romea Sanese and Way of St. Jacopo observe traditional dining hours. Lunch service typically runs from 12:30 to 2:30 p.m., and dinner starts around 7:30 p.m. — earlier than in southern Italy but later than what many American travellers expect. In smaller towns like San Donato in Poggio or Pescia, restaurants may close entirely on Monday or Tuesday. If you’re driving between meals, keep a insulated water bottle and some shelf-stable snacks in the car, because finding an open bar for a panino at 3:30 p.m. is not guaranteed.
Italian Etiquette on the Road and Trail
On the road, Italian drivers expect you to move over on winding mountain roads — if someone is behind you, pull into the next passing area rather than speeding up. On foot, greet anyone you pass on the trail with a simple “buongiorno” before noon or “buona sera” after. It’s not required, but it’s noticed. When visiting churches along the routes — the Basilica of San Francesco in Siena or the Sanctuary of La Verna on the Way of Francis — cover your shoulders and knees. Many churches post dress code signs at the entrance, and staff will turn away visitors in tank tops or shorts regardless of how hot the day is.
- Check your rental car’s clearance before attempting unpaved sections of the Via Romea Sanese — a compact SUV handles the gravel better than a sedan.
- Book accommodation in villages along the routes at least two weeks ahead during September and October, when harvest season fills rooms.
- Carry cash for tolls, parking, and small purchases in villages — many rural bars and shops don’t accept cards for transactions under €10.
Questions About Driving and Walking Tuscany’s Historic Routes
Can you drive the entire Via degli Dei?
No — the Way of the Gods is primarily a hiking and cycling route. Some sections follow paved roads that are accessible by car, but the Apennine crossings include narrow dirt paths and forest trails where vehicles aren’t permitted. Stick to the Via Romea Sanese if you want a driving route with similar scenery.
Do I need a special permit to drive on these routes?
No permit is required for the routes themselves, but you do need to navigate Florence’s ZTL before you reach them. If your accommodation is inside the historic centre, confirm that the hotel registers your plate. Otherwise, park outside the ZTL and walk or take a taxi to your lodging.
Are the routes safe for solo female travellers?
Yes, with standard precautions. The Via Romea Sanese and Way of St. Jacopo pass through inhabited villages with regular foot traffic. The Via degli Dei is more remote — let someone know your daily plan and carry a portable phone charger since mountain sections can drain your battery faster than usual.
What’s the biggest mistake people make on these routes?
Underestimating driving time. A 50-kilometre stretch on the Via Romea Sanese can take two hours because of narrow roads, slow farm vehicles, and unpaved sections. GPS estimates based on main roads don’t apply here. Add 30–40% to whatever your navigation app suggests.
Is the Way of Dante worth doing if I’m not a literature fan?
It depends. The route connects Florence and Ravenna through landscapes that Dante actually travelled, but at 380+ kilometres across 20 stages, it’s a serious commitment. If you’re more interested in scenery than literary history, the Via Romea Sanese or Way of St. Jacopo offers similar terrain in a shorter distance.
The thing that stayed with me after driving the Via Romea Sanese wasn’t the famous view from Piazzale Michelangelo — it was the moment near Castellina in Chianti when the road dropped into a valley of vineyards with no other cars in sight, and the only sound was gravel under the tyres. That kind of quiet doesn’t exist on the autostrada. If you’re planning a trip that includes Florence, consider a day trip into the surrounding countryside — the roads themselves are worth the drive.
Sources and further reading
Walking around Florence: 6 itineraries among history and nature. Visit Tuscany, 2024.
Florence’s Timeless Allure: A Historian’s Journey Through Art and Architecture. Peek, 2024.
A Timeless Journey Through Florence. The Wandering Passport, 2024.