10-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, San Gimignano, Santa Maria degli Angeli, 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

Experience the freedom of the open road on an unforgettable 10-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Pisa, Florence, Siena, San Gimignano, Greve in Chianti, Montefioralle, Santa Maria degli Angeli, Rome, and Orvieto.

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, 2 nights in Florence, 2 nights in San Gimignano, 1 night in Santa Maria degli Angeli, and 2 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, Siena, San Gimignano, Greve in Chianti, Montefioralle, Santa Maria degli Angeli, 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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  • Knights' Square
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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.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Pisa. Make yourself at home and unwind before heading out again.

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 10-day road trip in Italy!

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Day 2

Day 2

  • Pisa
  • Florence
  • More

Drive 88 km, 1 hour 39 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • More

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Pisa and Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

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

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

Relax and look forward to more memorable moments to come!

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Day 3

Day 3

  • Florence
  • More

Drive 9 km, 1 hour 19 min

  • David
  • Galleria dell'Accademia
  • Central Market
  • Cathedral of Santa Maria del Fiore
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

You’ll stay in Florence 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.

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

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

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Day 4

Day 4

  • Florence
  • San Gimignano
  • More

Drive 117 km, 2 hours 16 min

  • Palazzo Salimbeni
  • piazza del Campo
  • Siena Cathedral
  • Porta San Giovanni
  • Parco della Rocca
  • Piazza del Duomo, San Gimignano
  • More

Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of Siena and San Gimignano. At the end of the day, enjoy the comforts of a top-rated hotel in San Gimignano, where you'll spend 2 nights.

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

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

Raise your glass to another unforgettable day in Italy!

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Day 5

Day 5

  • San Gimignano
  • More

Drive 97 km, 2 hours 12 min

  • Castle of Verrazzano
  • Fattoria Viticcio
  • Villa Calcinaia - Conti Capponi
  • More

On day 5 of your road trip, you’ll start and end your day in San Gimignano, where you have 1 night left to stay.

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

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

Raise your glass to another unforgettable day in Italy!

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Day 6

Day 6

  • San Gimignano
  • Assisi
  • More

Drive 169 km, 3 hours 29 min

  • Basilica of San Francesco d'Assisi
  • Porta San Giacomo
  • Portico of Monte Frumentario
  • Rocca Maggiore
  • Basilica di Santa Chiara
  • Piazza del Comune
  • More

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Santa Maria degli Angeli. When you’re not sightseeing, take time to relax at your chosen hotel in Santa Maria degli Angeli, where you’ll be staying for 1 night.

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

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

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

  • Assisi
  • Rome
  • More

Drive 185 km, 3 hours 29 min

  • Colosseum
  • Roman Forum
  • Pantheon
  • Trevi Fountain
  • Spanish Steps
  • Piazza di Spagna
  • More

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 2 nights.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. 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 Rome, 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 8

Day 8

  • Rome
  • More

Drive 11 km, 1 hour 25 min

  • Vatican Museums
  • St Peter's Basilica
  • Sistine Chapel
  • piazza del Popolo
  • Piazza Navona
  • Via del Corso
  • More

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Rome, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Vatican City and Rome.

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

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.

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

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Day 9

Day 9

  • Rome
  • Pisa
  • More

Drive 370 km, 4 hours 48 min

  • Well of St Patrick
  • Orvieto Cathedral
  • Museo dell'Opera del Duomo
  • Orvieto subterranea
  • Torre del Moro Orvieto
  • Pozzo della Cava
  • More

Dive into day 9 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Orvieto. At the end of the day, you’ll unwind at one of the finest accommodations in Pisa, where you'll spend 1 night.

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

Pisa 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 Pisa.

Relax and recharge in preparation for another adventurous day in Italy!

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Day 10

Day 10

  • Pisa - Departure day
  • More
  • Palazzo Blu
  • More

Day 10 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.

We guarantee

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

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