12-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Siena, and Rome

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Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina
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Description

Escape the ordinary with this exciting 12-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Pisa, 3 nights in Florence, 3 nights in Siena, and 3 nights in Rome. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have you covered.

Upon arriving in Pisa, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Pisa, Florence, Greve in Chianti, Castellina in Chianti, Siena, San Gimignano, Castelnuovo dell'Abate, Montalcino, Pienza, Castiglione d'Orcia, Rome, and Orvieto, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodations, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Driver’s age is 30 - 65
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Pick-up: 10:00
Drop-off: 10:00

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Day 1

Day 1

  • Pisa - Arrival day
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  • “Tuttomondo” (Keith Haring)
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Welcome to Pisa, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night discovering what to see in Pisa before embarking on the next leg of your journey.

Pisa is a beautiful city with plenty to discover. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Pisa. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a central location for easy access to key areas in the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.

Raise a toast to the start of your 12-day road trip in Italy!

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Day 2

Day 2

  • Pisa
  • Florence
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Drive 90 km, 1 hour 49 min

  • Knights' Square
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Campo santo
  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • More

Your itinerary for day 2 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 3 nights.

At the end of the day, you will drive to Florence, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 3

Day 3

  • Florence
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Drive 4 km, 1 hour 5 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • More

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 4

Day 4

  • Florence
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Drive 101 km, 2 hours 26 min

  • Castle of Verrazzano
  • Tumulo di Montecalvario
  • Rocca di Castellina in Chianti
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On day 4 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Throughout the day, make sure to take breaks to appreciate the surroundings.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day 5

Day 5

  • Florence
  • Siena
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Drive 79 km, 1 hour 23 min

  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
  • Tower of Mangia
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On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 3 nights.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

Head back to your accommodation in Siena and get some rest to prepare for another magical day of your road trip in Italy.

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Day 6

Day 6

  • Siena
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Drive 83 km, 1 hour 37 min

  • Rocca di Montestaffoli
  • Town Hall, Picture Gallery and Great Tower
  • Piazza del Duomo, San Gimignano
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On day 6 of your road trip, you’ll start and end your day in Siena, where you still have 2 nights left. You'll spend part of the day exploring places of interest outside the immediate city, including San Gimignano.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for a true cultural experience.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

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Day 7

Day 7

  • Siena
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Drive 156 km, 3 hours 15 min

  • Abbey of Sant'Antimo
  • Fortress of Montalcino
  • Palazzo Piccolomini, Pienza
  • Rocca d'Orcia
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On day 7 of your road trip, you'll get the chance to experience Castelnuovo dell'Abate, Montalcino, Pienza, and Castiglione d'Orcia. At the end of the day, you'll drive back to Siena, where you still have 1 night left to stay.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Siena.

After a day of adventure, treat yourself to an exquisite dinner at one of Siena's best restaurants.

Relax and look forward to more memorable moments to come!

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Day 8

Day 8

  • Siena
  • Rome
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Drive 233 km, 3 hours 21 min

  • Villa Borghese
  • Spanish Steps
  • Piazza di Spagna
  • Trevi Fountain
  • Pantheon
  • More

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for a true cultural experience.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 9

Day 9

  • Rome
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Drive 15 km, 1 hour 1 min

  • piazza del Popolo
  • St Peter's Basilica
  • Sistine Chapel
  • Vatican Museums
  • Trastevere
  • Via del Corso
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You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Rome is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Rome.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day 10

Day 10

  • Rome
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Drive 9 km, 1 hour 19 min

  • Colosseum
  • Arch of Constantine
  • Roman Forum
  • Campo de' Fiori
  • Piazza Navona
  • Castel Sant'Angelo
  • More

You’ll stay in Rome for 1 night.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Savor another day of unforgettable experiences in Italy!

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Day 11

Day 11

  • Rome
  • Pisa
  • More

Drive 371 km, 4 hours 31 min

  • Orvieto Cathedral
  • Orvieto subterranea
  • Torre del Moro Orvieto
  • Pozzo della Cava
  • More

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Orvieto. At the end of the day, you will retreat to the hotel of your choice in Pisa, where will spend 1 night.

At the end of the day, you will drive to Pisa, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Pisa. Enjoy a relaxing evening as you savor delicious local cuisine.

Raise your glass to another unforgettable day in Italy!

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Day 12

Day 12

  • Pisa - Departure day
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  • Palazzo Gambacorti
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Day 12 of your road trip in Italy is your departure day. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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How it works

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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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