Driving Tuscany
Know before you go
Road Notes from Tuscany
Tuscany Regional Driving Guide
If you plan to stay a few days in Tuscany, I’d suggest renting a car for the duration of your stay, as there won’t be able to rely on Uber or taxis. Go with the smallest car you are comfortable with.
Don’t drive if you cannot just sample wines. Most pours are 1-1 .5 once samples (Restaurant pour is 5oz, Home pours 10oz ) know your limits. Tip: just Share wine samplings, or share a single glass.
If you have any kind of motion sickness, Tuscany is not for you, rolling and twisting hills, blind spots and tight turns are not for faint of heart.
Locals will ride your bumper, don’t let them push you past your driving limits of comfort, they will pass you when they can.
You will travel of gravel roads, smooth and wide to one car and very rocking… these are considered actual roads, not just the paths to the winery.
You will have to back up and move into hedges along the road, in order for oncoming cars to get by.
You will absolutely need GPS, and on the cars display, youll need to zoom in on the multiple round about exits.
You will miss a turn, or round about exit, accept it and don’t let it ruin you day
The speed limit will change very often, 30-60-90, 30-50-90.
Speed traps are real and listed on GPS as they are marked, you will get a ticket later from rental company.
Get your Internation driver’s license
Take the long routs to avoid long gravel roads that don’t seem logical to drive on for more than 100 m.
Finding a Parking space in the main city’s of Montepulciano, Montalcino etc can quickly lead to divorce or separation, or at minimum ruined the day… accept this beforehand. There are many parking small parking lots, Most will be full, the closer to the town. You will miss the turn or round about exit, and find yourself driving into the town’s main walk ways. Roads are tight with tight switch backs that you miss. Use GPS and put in parking and you’ll see many. Also bring coin money as they don’t all accept card or don’t work.
Montepulciano is the easiest drivable area, wineries are all in close proximity and along main roads, also with the most walks of 19 of 25 wineries
San Gimignano would be the second easiest drivable area, wineries are all in close proximity and along main roads, however not as many walk ins 13 of 25 wineries.
Chianti regions are drivable with more small towns in between destination, southern Chianti tends to have a few more gravel roads, and with about half of the wineries are walk ins.
Montalcino may be the most scenic drive know for val d'orcia, however has more side road and gravel roads than other regions, will require more planning as there only 6 walk in wineries in the region.
Renting a car
Wine and Driving
Tuscan Roads
Parking
Good to Know
Driving Tuscany
“The roads, the curves, the gravel, and the unforgettable views.”
“The roads of Tuscany are part of the journey.”
KNOW BEFORE YOU GO
Renting a Car
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Rent the smallest car you are comfortable with.
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You won’t be able to rely on Uber or taxis.
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Get your International Driver’s License.
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GPS is essential — use the car display and zoom in on roundabouts.
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Bring coin money for parking.
Wine & Driving
Tuscan tastings are generous. Know your limits and share tastings whenever possible.
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Don’t drive if you cannot just sample wines.
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Most pours are 1–1.5 oz samples.
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Restaurant pours are approximately 5 oz.
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Home pours may be closer to 10 oz.
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Tip: Share wine samplings or share a single glass.
Tuscan Roads
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You will travel on gravel roads — from smooth and wide to one car and very rocky.
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These are actual roads, not just winery paths.
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Back up and pull into hedges to let oncoming cars pass.
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Expect rolling hills, blind spots, tight turns, and narrow roads.
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Locals will ride your bumper — let them pass when they can.
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Don’t let them push you beyond your comfort level.
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If you have motion sickness, Tuscany may not be for you.
Parking
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Parking in hill towns can test your patience (and relationships).
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Many small parking lots will be full the closer you get to town.
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You may miss a turn or roundabout exit and end up inside town walkways.
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Use GPS and search “parking” ahead of time.
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Many parking lots don’t accept cards or their machines don’t work.
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Bring coins whenever possible.
Good to Know
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You will miss a turn or roundabout exit — accept it and move on.
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Speed limits frequently change: 30–60–90 or 30–50–90.
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Speed traps are real and marked on GPS.
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Tickets may later arrive through the rental company.
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Take longer routes to avoid rough gravel roads when possible.
ROAD NOTES FROM TUSCANY
“You will miss a roundabout exit. Accept it and enjoy the scenery.”
“Locals WILL ride your bumper. They know the roads — let them pass when they can.”
“A gravel road does not mean you’re lost — it means you’re in Tuscany.”
“Parking in hill towns may test your patience more than the roads themselves.”
“The most scenic roads are often the least logical.”
REMEMBER
Drive with patience, respect the locals, and leave plenty of time.
The journey is just as beautiful as the destination.
TUSCANY REGIONAL DRIVING GUIDE
RegionEase of DrivingGravel RoadsWalk-In WineriesNotes
MontepulcianoEasyLow19 / 25Easiest drivable area. Wineries are in close proximity along main roads with the highest number of walk-ins.
San GimignanoEasyLow13 / 25Second easiest drivable area. Wineries are close together along main roads, though with fewer walk-ins.
ChiantiModerateMedium~50% of wineriesMore small towns between destinations. Southern Chianti has more gravel roads.
MontalcinoAdvancedHigh6 Walk-insMost scenic drive known for Val d’Orcia, but has more side roads and gravel roads requiring additional planning.
“Take the long way, enjoy the views, and let Tuscany unfold one turn at a time.”
Your Driving Adventure Through Tuscany Wineries Awaits
We Always rent a car. While Tuscany does have some train service between major cities and limited bus routes, the true magic of the region lies far beyond where public transportation can take you. Florence is typically the easiest place to pick up a rental car, with Siena being another convenient option once you've arrived in the heart of Tuscany.
Driving Tuscany's winding roads can be an adventure in itself, but the freedom it provides is one of the greatest gifts of the journey. A car allows you to travel at your own pace, turning every day into an opportunity for discovery. You can leave the crowds behind, follow a scenic road simply because it looks interesting, and stumble upon places that never appear in guidebooks.
Driving through Tuscany is about much more than getting from one destination to another—it's about discovering everything in between.
Unlike many European destinations, Tuscany's greatest experiences often lie beyond the reach of trains and buses. Hidden wineries, quiet villages, scenic overlooks, family-owned restaurants, and winding vineyard roads are scattered throughout the countryside, waiting to be discovered.
Whether you're planning to visit Chianti, San Gimignano, Montalcino, or Montepulciano, having your own vehicle gives you the freedom to explore Tuscany at your own pace.
Some of Tuscany's most memorable experiences happen between destinations rather than at them. You might round a corner and find a hilltop village perched above a sea of vineyards, stop at a roadside viewpoint overlooking the Val d'Orcia, or pull over to photograph a row of cypress trees glowing in the late afternoon sun. A small family-owned winery, a quiet local trattoria, or a village festival may become the highlight of your trip simply because you had the freedom to stop.
The beauty of Tuscany isn't confined to Florence, Siena, San Gimignano, or Montalcino. It's found in the countless roads that connect them. Every drive reveals another postcard-worthy landscape of vineyards, olive groves, medieval stone farmhouses, and rolling hills stretching to the horizon.
Driving Tuscany's winding roads can be an adventure in itself, but the freedom it provides is one of the greatest gifts of the journey. A car allows you to travel at your own pace, turning every day into an opportunity for discovery. You can leave the crowds behind, follow a scenic road simply because it looks interesting, and stumble upon places that never appear in guidebooks.
Having a car transforms Tuscany from a vacation into an exploration. It allows you to linger longer over lunch, chase a sunset across the countryside, or spend an extra hour at a winery that captures your heart. In Tuscany, the journey is often just as rewarding as the destination, and the freedom to explore without a schedule is what makes the experience unforgettable.
Where to Rent a car for your Tuscany Journey
✈️ Florence Airport
Best if your trip starts in Florence and you want to explore Chianti, San Gimignano, Siena, Val d’Orcia, Montepulciano, or the Tuscan countryside. (Do not rent from Florance Train Station) Driving in and out of Florance T will test your Marriage.
✈️ Pisa Airport
A great option if you’re visiting western Tuscany, Lucca, Pisa, Volterra, San Gimignano, the coast, or if you find better flight prices into Pisa.
✈️ Bologna Airport
Useful if you’re combining Emilia-Romagna and Tuscany, or if flights are cheaper. From Bologna, you can drive south toward Florence, Chianti, or the Tuscan countryside.
✈️ Rome Airports
A good choice if your itinerary includes southern Tuscany, Val d’Orcia, Montepulciano, Pienza, Montalcino, or if you’re combining Rome and Tuscany in one trip.
✈️Vience Airport
Best if your your doing trips to Florence ae Chianti, San Gimignano, Siena, Val d’Orcia, Montepulciano, or the Tuscan countryside. Faster than taking a Train to Florance or Seina
🚆 Seina Train Station
Best if your trip starts in Central Tuscany and you want to explore Chianti, San Gimignano, Siena, Val d’Orcia, Montepulciano, or the Tuscan countryside.
Pro Tip:
Choose the major rental car companies. Smaller local rental companies may be less expensive, however less responsive to issue in the off hours. They also have different business hours that limits your pick-up and drop off time
Driving In Tuscany Tips
Driving tips in Tuscany:
✔️ Choose a small car for narrow village streets
✔️ Avoid driving into Florence’s historic center because of ZTL restricted areas
✔️ Park outside old towns and walk in
✔️ Check parking before visiting popular villages
✔️ Book early in summer for better prices
✔️ Don’t overplan — scenic drives are part of the experience
✔️ Always watch for ZTL signs in historic centers
My advice? Don’t rent a car for your days inside Florence. The city is best explored on foot.
Driving Val d'Orcia
If you're traveling between Montalcino and Montepulciano, don't rush the drive. In between lies the breathtaking Val d'Orcia—one of the most beautiful landscapes in all of Italy. Rolling hills, endless vineyards, ancient stone farmhouses, winding cypress-lined roads, and golden fields stretch to the horizon. It's so vast and spectacular that no single photograph can truly capture its beauty. This is one of those rare places where you'll find yourself pulling over every few miles just to admire the view.
How to Choose between Montalcino and Montepulciano
Choosing between Montalcino and Montepulciano really comes down to what kind of wine experience you're after. If you're a fan of the world-famous Brunello di Montalcino, Montalcino is your destination. If Vino Nobile di Montepulciano is more your style, Montepulciano offers an equally memorable experience with a different personality.
For first-time visitors, Montepulciano is often the easier region to explore. The roads are straightforward, wineries are close together, and more than half welcome visitors with convenient walk-in tastings—perfect for a spontaneous day of wine tasting. Within a 12 km (7.5 mile) radius you'll find approximately 25 wineries, making it easy to visit several in a single day.
One of our Favorite Winery Areas in Montepulciano
One of our favorite areas is a stretch of road where, within about 1 km (0.6 mile), you can visit Fattoria Svetoni, Gracciano della Seta, and Poliziano—three outstanding wineries, each offering its own unique style and atmosphere. While you're nearby, don't miss Bindella – Tenuta Vallocaia, another exceptional estate that consistently ranks among our favorites.
Our Favorite Winery Areas in Montalcino
If you prefer a quieter, more intimate experience, Montalcino offers charming agriturismos, boutique estates, and unforgettable vineyard settings. Many wineries here require advance reservations, but the personalized tastings and peaceful countryside make the extra planning worthwhile. Castello Banfi Hospitality offers one of the widest selections of tours, tastings, restaurants, and accommodations, while Corte Pavone Winery rewards visitors with some of the most spectacular vineyard views in the region.
Be sure to spend time wandering the historic center of Montepulciano itself. The medieval hill town is home to six wineries located right in town, allowing you to explore centuries-old underground wine cellars without ever moving your car.
After a day of exploring, reward yourself with dinner at OSTERIA ACQUACHETA in Montepulciano. Famous for its legendary Florentine steak and unforgettable atmosphere, it's one of our favorite restaurants in Tuscany. Reservations are highly recommended—this local favorite fills up quickly.
Take your time, enjoy the drive, stop often, and let the roads lead you to places you never expected. That's where Tuscany creates its best memories.
Enjoy the journey… and salute! 🍷
Tuscany Winery Guide
To make planning easier, we rely on the Tuscany Wineries Guide, which maps every winery, highlights available amenities, and includes 2026 tasting prices, and with many Wineries very close to each other, the maps help you maximize your time while avoiding unnecessary driving.
Why Renting a Car is the Best Way to Experience Tuscany
Most travelers arrive in Florence, making it the ideal place to pick up a rental car before heading into wine country. Siena is another excellent starting point if you're already exploring southern Tuscany.
While public transportation connects many major cities, it rarely reaches Tuscany's boutique wineries, agriturismos, and rural landscapes.
Having a car means you can:
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Stop whenever a breathtaking view appears.
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Visit multiple wineries in one day.
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Take A Cooking Class
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Do A Truffle Hunt
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Discover hidden villages.
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Enjoy scenic vineyard roads.
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Explore at your own pace.
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Stay at countryside agriturismos.
In Tuscany, the journey often becomes the highlight of the trip.
If you want to skip the hassle of booking tastings and driving yourself, taking guided wine tasting tours are a great option. Bravissimi from Grape Tours will take care of you offering Premium Small-Group and Private Tuscany Wine Tours.