4-Day Road Trip Itinerary Through Tuscany

Imagine a region where rolling hills meet picturesque medieval towns, where every corner reveals a scene so stunning it could inspire poetry. Welcome to Tuscany, a land of art, culture, and delectable cuisine that beckons travelers from all over the globe. This guide is designed to help you navigate the beauty of this enchanting place, particularly if you're planning to explore it by car.

Whether you're a history buff, a foodie, or simply looking to soak in the breathtaking landscapes, Tuscany offers an unforgettable experience. Buckle up as we dive into the ultimate guide for a road trip through Tuscany, featuring everything from itineraries to must-see attractions.

Comprehensive Guide for Driving Through Tuscany

Ready to hit the road? Here’s everything you need to know for your Tuscan adventure, including essential tips and key details.

1. Overview of the Route Through Tuscany

Before you embark on your journey, it's important to familiarize yourself with the basics of the route:

• Starting Point: Florence
• End Point: Pisa (you can create a loop back to Florence)
• Total Duration: 4 days of driving (7 days if including Florence and Pisa)
• Total Distance: Approximately 640 km
• Type of Transport: Rental car (a compact car is sufficient for couples)

2. Suggested Itinerary for a Car Trip in Tuscany

Your adventure should ideally start in Florence and end in Pisa. This route will take you through three of the most famous regions in Tuscany:

• Chianti
• Val d'Orcia
• Maremma

While the driving route spans 4 days, we recommend spending at least two days in Florence before setting out and one additional day in Pisa at the end.

› Map of the Route

To help you visualize your journey, here’s a map outlining key locations along the route:

3. Stages of the Journey

This section offers a detailed breakdown of each stage, along with links to articles where you can read about our experiences and practical tips for planning your trip (where to park, where to eat, where to stay, etc.):

› Stage 0: Florence

• Travel Guide to Florence
• Accommodation in Florence

› Stage 1: Florence to San Gimignano

• Total Distance: 115 km
• Must-See Stops: Greve in Chianti, Montefioralle, Panzano in Chianti, Radda in Chianti, Castellina in Chianti, and San Gimignano
• Read the article
• Accommodation in San Gimignano

Your first day will focus on traversing the Chianti region, visiting charming towns such as Montefioralle and Castellina in Chianti. Be sure to make one of your stops in San Gimignano, known for its medieval towers and often referred to as "the Manhattan of the Middle Ages." You won't want to miss it, whether it’s day or night.

› Stage 2: San Gimignano to Montepulciano

• Total Distance: 130 km
• Must-See Stops: Colle di Val d’Elsa, Siena, Montalcino, San Quirico d’Orcia, Pienza, and Montepulciano
• Read the article
• Accommodation in Montepulciano

As you leave San Gimignano, make a pit stop in Colle Val d'Elsa for breakfast. Your next major stop will be Siena, a city renowned for its iconic plaza, where the thrilling Palio horse race occurs. Conclude your day in Montepulciano, perched high atop a hill, offering incredible views of the surrounding area.

› Stage 3: Montepulciano to Pitigliano or Sorano

• Total Distance: 125 km
• Must-See Stops: Monticchiello, Bagno Vignoni, Castiglione d'Orcia, Terme Libere di San Filippo, Radicofani, Pitigliano, and Sorano
• Read the article
• Accommodation in Pitigliano / Accommodation in Sorano

This stage takes you through some of the most scenic roads in Tuscany, nestled in the heart of the Val d'Orcia region. Don't miss the chance to dip into the hot springs of San Filippo and explore the stunning cliffside towns of Pitigliano, often called "little Jerusalem," and Sorano, one of the most captivating spots on your journey.

› Stage 4: Pitigliano or Sorano to Pisa

• Total Distance: 270 km
• Must-See Stops: Etruscan Necropolis of Sovana, Saturnia Hot Springs, Montemerano, Larderello, and Volterra
• Read the article
• Accommodation in Pisa

After a leisurely breakfast, head to the stunning Saturnia Hot Springs, known for their vibrant blue waters. Take some time to relax before continuing to Volterra, a significant Etruscan site. Finally, end your journey with a visit to Pisa and its iconic Leaning Tower.

4. Renting a Car in Tuscany

As you've seen, we chose to pick up our rental car in Florence and return it in Pisa. Since these are different locations, you might incur a one-way fee (between €60 and €100) when making your reservation. However, we believe this is worth it if you have limited time. We paid around €65 for a 4-day rental through Auto Europe. Prices may have risen since the pandemic, so it’s good to check in advance.

A compact car (like a Fiat 600 or Punto) is more than sufficient, as the roads are mainly secondary with little traffic. Additionally, a smaller vehicle makes finding parking easier, especially in cities like Siena, San Gimignano, or Pisa.

⭐ If you want to learn more about driving in Italy and how to rent a car, check out our guide for renting a car in Italy.

5. Budgeting for a Car Trip in Tuscany

Calculating your trip budget can be tricky as it depends on various factors like travel style, accommodation choices, dining, and the season. However, we can provide a rough estimate based on our experience:

We dedicated an entire article to how much a trip to Italy costs, but here’s a summary table outlining our total estimated budget per person for a couple:

6. Top 10 Must-See Places on Your Tuscany Trip

If we had to choose ten places that you absolutely cannot miss in Tuscany, they would be:

• San Gimignano
• Colle di Val d’Elsa
• Siena
• Montepulciano
• Sovana
• San Filippo Hot Springs
• Pitigliano
• Sorano
• Saturnia Hot Springs
• Volterra

This journey through Tuscany is undoubtedly one of the most inspiring road trips in all of Italy. So, what are you waiting for? Book your car and start planning your trip! We’re confident that upon your return, you'll find yourself longing to explore more of Tuscany’s hidden treasures.

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