Tuscany Road Trip Itinerary: The Best of Tuscany

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Tuscany is one of the most popular tourist destinations in Italy because this central region of the country is renowned for its diversity. A Tuscany road trip can truly cater to any taste, being a food and wine haven for travelers, as well as being a cultural, artistic and historic marvel.

There are rolling hills, UNESCO World Heritage city centers, medieval villages, world-class wineries, and spectacular coastline. With so much to offer, the best way to experience the region is on a road trip.

This gives you the freedom to get out into the countryside to explore the lesser-known wonders in your own time.

Start your journey in Florence, the Renaissance heart of Europe, before exploring the Chianti wine region, the medieval center of Siena and of course, the classic leaning tower of Pisa.

There is a lot more to our Tuscany road trip than that though, so to guide you through the hills and along the beaches, here is our ultimate guide to planning your own adventure.

Don’t leave home without: Lonely Planet Florence & Tuscany (Travel Guide)

Planning Your Tuscany Road Trip

Aerial View of Fields in Tuscany- Road Trip

The ultimate Tuscany road trip will take you through some of the most pristine Italian countrysides, as you travel from classic city destinations to charming rural villages. It’s the best way to experience this part of the world, as you’ll be able to travel as fast as you want or as slow as you want.

Getting Started

Starting your trip in Florence will give you the chance to either pick up your rental car at the airport or spend a few days in the city before picking one up in the center, to begin the road trip itself.

Florence has excellent flight connections across Europe and is the perfect base for starting and ending the trip. There are also great domestic connections across Italy, including the high-speed rail, if you are only looking at a Tuscany Road Trip, rather than a countrywide road trip.

Rental Cars & Driving

You can book rental cars in advance online, for pick up when you arrive, and with a lot of competition, you can get some excellent deals ahead of time.

Be sure to check what insurance is provided with your rental, as you won’t want to get caught out. You’ll also want to check your license is valid in Italy – most driving licenses are for short periods at the very least – and you’ll want to check if roadside assistance is included.

Driving in the cities can be rather hectic, as most have narrow, medieval streets – which is part of the charm! – so it can get some getting used to.

In the countryside, there are lots of winding, rural roads, so always be aware. There are also plenty of wineries to stop off at, but just ensure the driver doesn’t indulge over the limit!

Need to book a car for your road trip adventure? We use Discover Car Hire for comparing car prices to find the best deal. They search both local & international rental companies.

Drive Times

For the itinerary below, you’ll never need to drive for longer than 2 hours at a stretch between each destination, giving you plenty of opportunities to actually explore the places you are traveling to.

We’d recommend at least one night in each of the destinations below, with perhaps two or more in Florence overall. Of course, this is your Tuscany road trip though and the joy of driving is that you can tailor the trip to your own preference.

Read reviews and check prices with our Hotel Search Engine, that gives you the best hotel deals found on the web. Our search engine pulls results from all of the major booking places, including Expedia, Hotels, Booking and more. All the options, all the deals, all in one place and just for you.

Top Places to Visit in Tuscany


Florence, Italy skyline

Your trip begins and ends in Florence, the capital of Tuscany and the heart of the region. This is where you pick up your rental car after flying in or catching the train but don’t leave straight away, because the city is a must-visit destination in its own right.

Florence is one of the major cultural centers in Italy and is often cited as the ‘birthplace of the Renaissance’. The medieval city center is awash with beautiful architecture, incredible basilicas and cathedrals, and endless museums and art galleries.

Call in at the Uffizi Gallery to see some of the most iconic works of art from European painters and sculptors on display, and don’t miss the Galleria dell’Accademia for a glimpse of Michaelangelo’s David.

Indulge in a true taste of Florence on this food and walking tour. Led by a foodie guide, travel through the streets of the Renaissance city and stop at the top local haunts.

Check out the fresh produce at the San Lorenzo Market, try the bold flavors of an Italian coffee, and peruse a Florentine delicatessen. You’ll sample plenty of specialties along the way, including cheeses, bread, olive oils, gelato, and Italian wine.

Accommodation in Florence: Hotel Pendini – great breakfast and location

Greve in Chianti

Vineyard in Tuscany

After enjoying the historic, Renaissance-era sights of Florence, it’s time to drive out into the countryside, to begin your Tuscany road trip. A short, but pleasant 30-kilometer drive will take you along winding, rural roads to the small town of Greve in Chianti.

The Chianti region is one of the most famous wine-producing regions in Italy, and here you can find wineries in beautiful settings around every corner.

Call in at the local wineries, enjoy some fresh local cheese, olives and cured meats, and of course a few tastings. You will want to spend the night in Greve to truly appreciate the fine wines.

Accommodation for Greve: Albergo del Chianti – beautiful pool and great location


Arezzo, Italy

In the morning, set off south-east to the edge of Tuscany to visit the city of Arezzo. Just over an hour of straight driving will bring you from Greve in Chianti to Arezzo, where you can find an off the beaten track city that’s full of intriguing history.

Arezzo has a history dating back to at least the 9th century BC. Almost 3000 years of human history can be discovered here, but unfortunately, much of the ancient center was destroyed during the second world war.

For that reason, many travelers choose to visit other, more preserved locations in Tuscany, but the big benefit to that is the fact that Arezzo is much quieter, and in many ways more authentic culturally than other Tuscan destinations.

You can visit old churches, the beautiful main plaza and enjoy glorious views of the Tuscan countryside from the city’s hilltop position.

Indulging in local wine is a must when you visit Tuscany. On this private tour, you’ll go behind-the-scenes at one of the region’s most scenic and esteemed wineries, located just on the outskirts of Arezzo.

Learn about organic winemaking processes when you tour the vineyards, delve into the cellar to discover how wine is aged, and finally taste three organic wines, along with locally made pecorino cheese and cured meats.

Accommodation in Arezzo: Hotel L’Aretino – great breakfast and good location


Montepulciano, Italy

An hour’s drive south of Arezzo takes you to Montepulciano, a wonderfully well preserved medieval town. Like many Tuscan settlements, Montepulciano was founded on a high hilltop, offering the inhabitants protection, and today offering tourists excellent views.

In Montepulciano, you’ll want to park up and stroll through the charming streets, admiring the Rennaisance era architecture that the city is famous for.

Although you can easily see all the major sights in a few hours, it’s worth spending the night here, because Montepulciano is well regarded as a foodie destination.

Enjoy a late evening indulging in excellent local dishes and wine, including the high-quality Vino Nobile which is produced locally.

Explore a wine cellar in Montepulciano with this tasting and tour. See rows of large oak barrels full of aging wine and learn about how it is made. Taste three local wines alongside pecorino cheese, Tuscan salami, and bruschetta.

Accommodation in Montepulciano: Etruria Resort & Spa – splurge a little on this lavish oasis in Tuscany

Val D’Orcia

Perfect road trip along Val D’Orcia, Tuscany

Montepulciano makes for a great base from which to drive out into some of the most spectacular Tuscan countrysides in the region. Val D’Orcia is a long valley that leads towards the city of Siena, and the best part of driving through this part of Tuscany is the landscapes.

You’ll be stopping on the side of the country roads to photograph the incredible scenery, calling in at small villages and rural farmsteads and enjoying the great, open air.

This is your Tuscany road trip at its best, so just enjoy the drive and enjoy the outdoors.


Tuscany landscape, Italy

The next destination on the Tuscan road trip itinerary is Siena. This is one of the larger cities in Tuscany, and also one of the most historic. Siena is one of the highlights of any Tuscan road trip, but you won’t be driving through the narrow, maze of cobblestoned streets, you’ll be walking.

Siena is famous for its twice-yearly Palio, a horse race through the city itself, and if you can time your trip with a visit to this cultural festival, then you’ll see one of the most fascinating spectacles in Tuscany.

Any time of the year though, the Renaissance architecture is, with numerous Palazzos and Duomos waiting to be explored.

Indulge in one of Italy’s most beautiful cities, Siena, during this sightseeing tour. An expert guide gives you an insider’s view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place.

Accommodation in Siena: Hotel Athena Siena – great parking and location

San Gimignano

San Gimignano, Italy

San Gimignano is a small town with a huge reputation because the extensive medieval walls are some of the best-preserved in Italy. The town is found atop a high hill, making this a dramatic sight to see as you drive towards the gates.

Inside San Gimignano, you’ll find even more medieval architecture, as towering above the walls are 14 stone towers, raised high to protect the town against attack.

There are few towns in Italy with such a high number of surviving towers, and this really is a must-visit stop on your Tuscany road trip. Most tourists just pass through, but hang around, spend the night and see the city without the crowds early in the morning.

Accommodation in San Gimignano: Leon Bianco – great breakfast and location right in downtown


Livorno coastline, Italy

From San Gimignano, it’s a one and a half-hour drive to the coast, where you can explore a different side of Tuscany in Livorno. This is an important port city, and you can enjoy some of the best seafood in Tuscany along the waterfront.

Using Livorno as your base, you can drive out along the coast in search of hidden beaches and secret spots, alongside superb views out over the sea.

There are many ways to discover coastal Livorno’s charms and a private walking tour of the city’s central market is certainly an engaging way to explore. Meet your guide at your local accommodation or near your port, and set off for the Mercato Centrale one of Europe’s largest markets.

Accommodation in Livorno: Hotel Villa Margherita Livorno – great views and a nice pool


Pisa street, Italy

The final stop on your Tuscany road trip will undoubtedly need to be Pisa. Despite its huge popularity amongst tourists and despite the crowds, it’s still a must-visit destination, if only to take a picture of yourself posing in front of the iconic leaning tower at the end of your trip.

Aside from the tower, Pisa also has a wealth of largely ignored Renaissance history, museums, and galleries too, alongside a great culinary scene. From Pisa, it’s a one and a half-hour drive to Florence, where you started the road trip.

Explore Pisa without the hassle of planning on a walking tour of the city’s highlights, from the Square of Miracles to Pisa Cathedral. In addition to navigating, your guide offers little-known facts and anecdotes about Pisa’s ancient history.

Accommodation in Pisa: Grand Hotel Bonnano – beautiful rooms and good location

Recommended Multi-Day Tuscany Tours

Tuscany Road Trip

If renting a car in a foreign country is not your thing, no worries! It is possible to join one of several amazing tours that will take you to all of the above places we mentioned and more. 

  • G Adventures Local Living Italy Tuscany- If you’ve ever wanted to forge a deeper bond with a destination, this is your chance. Centered in San Gimignano, this Local Living adventure places you in the heart of central Tuscany. You’re free to explore the town, visit vineyards, discover medieval highlights, or embrace your inner artist wandering the Tuscan countryside. If you’re looking for a deeper dive into Italian cities, there’ll be day trips to visit Siena and Florence. You’ll share the main accommodation with like-minded travelers and a CEO there to point you in the right direction. Prepare to fall in love with Italy.
  • G Adventures Wellness Italy– If serenity has a palpable form, surely it can be found under the Tuscan sun. This seven-day tour of Italy will have you second-guessing your departure date from the moment you land in Rome. After a morning yoga session and a leisurely day on the grounds of Palatine Hill and the Colosseum, your path will take you to lush landscapes of Tuscany. There, you’ll have ample time to saunter through welcoming villages, taste exceptional local food and wine, and cycle your way through the Tuscan hills. A dip in healing thermal waters will leave a rejuvenating warmth radiating through both body and mind long past your final stop in Florence.
  • Best of Italy Summer (Start and end in Rome! With the in-depth cultural tour Best of Italy Summer, you have a 13 day tour package taking you through Rome, Italy and 12 other destinations in Italy. Best of Italy Summer includes meals and more.)
  • Taste Of Italy (Start and end in Rome! With the discovery tour Taste Of Italy – 8 Days, you have a 8 day tour package taking you through Rome, Italy and 9 other destinations in Italy. Taste Of Italy – 8 Days includes accommodation as well as an expert guide, meals, transport and more.)
  • The Italian Dream (Start and end in Rome! With the coach/bus tour The Italian Dream, you have a 8 day tour package taking you through Rome, Italy and 7 other destinations in Italy. The Italian Dream includes accommodation in a hotel as well as an expert guide, meals, transport and more.)

More on Italy:

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If you need more help planning your trip, be sure to check out our Step by Step Trip Planning Guide where we break down our process for getting the trip planning process right every single time.

About Lina Stock

Lina is an award-winning photographer and writer that has been exploring the world since 2001. She has traveled to 100 countries on all 7 continents. Member: SATW, NATJA, ATTA, ITWA

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3 thoughts on “Tuscany Road Trip Itinerary: The Best of Tuscany”

  1. Epic pictures and well written!!! Thank you for sharing 🙂
    Now I need to go back to the places I missed …
    Thank you for sharing!

  2. Arezzo is my favourite among the listed; though I have not visited all. I would really recommend visiting Poppi for tasting the delicious Tuscany wine there!!!!!!!! Really had an awesome time there. Lina, you could have included Poppy too to this awesome article. Otherwise awesome! You have succeeded in drawing the splendid beauty of the places in the article.
    Thanks Lina.


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