9-Day Italy Road Trip from Pisa traveling east to Siena, Rome, and Florence

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Escape the ordinary with this exciting 9-day road trip through Italy. Explore the diverse landscapes and local cultures of Pisa, Siena, Rome, and Florence. Pack your bags, hit the road, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Pisa, 1 night in Siena, 3 nights in Rome, and 2 nights in Florence. 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 got 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, Siena, Rome, and Florence, 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, accommodation, 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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Day 1

Day 1 – Pisa - arrival day

  • Pisa - Arrival day
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  • Piazza dei Cavalieri
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Your road trip adventure in Italy begins as soon as you reach Pisa and pick up your car. You’ll stay in Pisa for 1 night and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Pisa is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Knights' Square or taking a stroll in the city center. 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 hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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

Have a fantastic dining experience at Ristorante Capodimonte Pisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Baribaldi Pisa offers an enticing alternative with its varied menu. Additionally, Restaurant -Pizzeria Il Mio Capriccio is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

Keep the evening going at Jeffer Cocktails & Friends, a great choice for enjoying the after-dinner hours with a drink. You could also go to Le Parisien Wine Bar, which offers a similarly pleasant setting and great drinks. Another option is Las Volta Cocktailbar, which provides an inviting environment for unwinding after a busy day out.

Raise a toast to the start of your 9-day road trip in Italy!

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Day 2

Day 2 – Pisa, and Siena

  • Siena
  • Pisa
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Drive 129 km, 2 hours 9 min

  • Leaning Tower of Pisa
  • Angelo Caduto
  • Cattedrale di Pisa
  • Piazza del Duomo
  • Camposanto
  • More

On day 2 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Pisa. In the evening, you’ll end up in Siena, where you will stay for 1 night.

When you’re ready for some sightseeing, make your way to Leaning Tower Of Pisa. This much-appreciated bell tower is rated 4.7 out of 5 stars in 116,882 reviews. Each year, 3,200,000 people visit this site to admire its unique features.

Next up is Angelo Caduto. This point of interest has an average rating of 4.5 out of 5 stars from 150 visitors.

Another top sightseeing recommendation is Pisa Cathedral. This cathedral has been rated 4.8 out of 5 stars in 8,361 reviews.

Piazza Del Duomo, Pisa is another attraction you have the opportunity to visit today. This square has an average rating of 4.7 out of 5 stars from 104,550 reviews.

To continue your sightseeing, head over to Campo Santo. This cemetery is rated an average of 4.6 out of 5 stars in 586 reviews.

When you’re done exploring for the day, you’ll drive to Siena, where you'll have a hotel waiting for you. Check in and spend some time relaxing before you head out to explore the city.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Dine in style at Antica Trattoria Papei, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Quattro Venti boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 3

Day 3 – Siena, Vatican City, and Rome

  • Rome
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Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 3 nights.

Set your GPS to Vatican City, Vatican City and hit the road. Expect a journey of approximately 2 hours 40 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Vatican City beckons with new experiences!

An excellent attraction to start your day with is Sistine Chapel. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Continue your journey at St. Peter's Basilica. This major basilica is rated 4.8 out of 5 stars by 131,043 travelers from near and far. Approximately 11,000,000 people come to this place of interest every year to enjoy a unique experience in Vatican City.

Vatican City is also the home of Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 visitors.

You can continue your self-guided sightseeing tour at Vatican Museums. A total of 1,612,530 people explore this attraction every year. Rated 4.6 out of 5 stars by 133,310 visitors, a visit to this top sight is time well spent.

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

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

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean, and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative, and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean, and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Sant' Eustachio Caffè offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

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

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Day 4

Day 4 – Rome

  • Rome
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Drive 13 km, 1 hour 10 min

  • Basilica Papale di Santa Maria Maggiore
  • Piazza Navona
  • Campo de' Fiori
  • Pantheon
  • Castel Sant'Angelo
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Day 4 offers a multitude of experiences. You will stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

Take the opportunity to see Basilica Di Santa Maria Maggiore. This attraction has an average rating of 4.8 out of 5 stars from 27,678 visitors.

Piazza Navona is another sightseeing hotspot in the area. This square has been rated an average of 4.7 out of 5 stars by 158,771 travelers.

Rome is also the home of Campo De' Fiori. Around 51,133 people have rated this square an average of 4.4 out of 5 stars.

Another place you’ll want to visit is Pantheon, which hosts up to 30,000,000 visitors every year. With an average rating of 4.8 out of 5 stars from a total of 189,682 reviews, a visit to this roman temple is a great idea.

This day of your vacation in Rome is also your chance to admire Castel Sant'angelo. This must-visit museum enjoys an average rating of 4.7 out of 5 stars from 72,431 reviews. Approximately 918,591 people travel to Rome every year to see this attraction with their own eyes.

If you have an appetite for more adventure, check out the fantastic selection of tours and tickets offered in Rome on this day of your trip. You'll find the most recommended ones below.

As you explore more of Rome, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Dine in style at DEROMA - Farine Romane, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out Centro. Known as a local hotspot, it’s a great choice for tonight in Rome.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

Say good night to Rome and look forward to another great day of your road trip in Italy!

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Day 5

Day 5 – Rome

  • Rome
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Drive 4 km, 54 min

  • Altar of the Fatherland
  • Campidoglio
  • Roman Forum
  • Colosseum
  • Circus Maximus
  • More

Day 5 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Begin your sightseeing with a visit to Altare Della Patria. This extraordinary architectural structure is rated an average of 4.8 out of 5 stars by 49,843 visitors. Each year, around 1,683,070 people visit this site to learn more about it.

Next, make your way to Capitoline Hill. This top attraction is a hill with an average rating of 4.7 out of 5 stars by 19,557 visitors.

We also recommend a visit to Roman Forum. This square is rated 4.7 out of 5 stars by 114,450 travelers.

If you’re keen to keep exploring, visit Colosseum. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 328,821 travelers. Around 7,400,000 people come to experience this place of interest every year.

Today is also your chance to spend some time at Circus Maximus. This circus is rated an average of 4.4 out of 5 stars by 44,741 travelers.

Don’t forget to check out all the popular tours and activities you can add to your travel plan. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Enjoy a delicious meal at Ristorante Tema, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Maccheroni, another top spot with a mouthwatering menu. You might also want to secure a reservation at RoYaL Art Cafè Roma. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

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Day 6

Day 6 – Rome, and Florence

  • Florence
  • Rome
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Drive 280 km, 3 hours 50 min

  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • Piazza del Popolo
  • Villa Borghese
  • More

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Drop by the renowned Trevi Fountain. This popular sculpture has been rated an average of 4.8 out of 5 stars by 343,494 visitors.

Another unforgettable place to experience is Piazza Di Spagna. Rated 4.7 out of 5 stars by 113,658 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Spanish Steps. This monumental staircase has been rated an average of 4.5 out of 5 stars in 57,211 reviews.

Another favorite attraction in the area is Piazza Del Popolo. This square and popular place of interest enjoys a rating of 4.6 out of 5 stars from 89,807 local and international travelers.

If you’re keen to explore even more, then consider a visit to Villa Borghese. With an average rating of 4.6 out of 5 stars from 69,749 travelers, this urban zone of rome is an attraction many avid travelers highly recommend visiting while in Rome.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative, and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary, and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 7

Day 7 – Florence

  • Florence
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Drive 4 km, 1 hour 10 min

  • Piazzale Michelangelo
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazza della Signoria
  • Basilica of Santa Croce in Florence
  • More

Day 7 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Be one of the day’s first visitors at Piazzale Michelangelo. This square is rated an average of 4.8 out of 5 stars by 77,744 visitors.

When you’re finished at Piazzale Michelangelo, head to Uffizi Gallery. This one-of-a-kind national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. Every year, approximately 2,011,219 travelers come here to experience the national museum for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars by 118,099 visitors.

If you’re keen to explore more, then consider a visit to Piazza Della Signoria. This square is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 66,956 visitors.

To round off your sightseeing experience, make your way to Basilica Of Santa Croce In Florence. This famous church is rated an average of 4.7 out of 5 stars by 28,544 travelers.

One of the most unique ways of discovering what else Florence has to offer is by going on a top-rated tour. Be sure to check out all the experiences Florence offers and add your favorites to your Italy travel package below.

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.

Treat yourself to a wonderful meal at Trattoria Da Burde, a top-rated dining spot in Florence. If you're in the mood for something new, try Ristorante Buca Mario, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Get a good night's sleep and look forward to another great day on the road in Italy!

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Day 8

Day 8 – Florence, and Pisa

  • Pisa
  • Florence
  • More

Drive 83 km, 1 hour 38 min

  • Cathedral of Santa Maria del Fiore
  • Accademia Gallery
  • Basilica of Santa Maria Novella
  • More

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Kick off the day at Cathedral Of Santa Maria Del Fiore, a top pick for today’s sightseeing. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Today is also your chance to visit Galleria Dell'accademia. Galleria Dell'accademia is a national museum with an average rating of 4.6 out of 5 stars from 34,429 reviews. Attracting more than 1,719,645 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

Central Market is another top attraction we highly recommend you visit today. This point of interest is rated an average of 4.4 out of 5 stars by 43,100 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Basilica Di Santa Maria Novella, Firenze (fi). This archives is rated an average of 4.7 out of 5 stars by 23,075 visitors.

When you’re done exploring for the day, you’ll drive to Pisa, where you'll have a hotel waiting for you. Check in and spend some time relaxing before you head out to explore the city.

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

Enjoy a lovely meal at Ristorante alle Bandierine, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Barrique Cocktail And Bistrot is another top choice with a popular menu. You could also check for a table at Filter Coffee Lab. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Cap off your dinner by heading to Bar Mocambo, ideal for a leisurely evening with a drink in hand. Tree is another bar that offers an enjoyable setting. Similarly, Chupiteria is also a popular place to go on a night out, perfect for relaxing and socializing.

Get a good night's sleep and look forward to another great day on the road in Italy!

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Day 9

Day 9 – Pisa - departure day

  • Pisa - Departure day
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  • Logge dei Banchi
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Day 9 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Pisa before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

Maximize your last day in Italy and go on a shopping spree in Pisa’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

Be one of the day’s first visitors at Logge Dei Banchi. This sightseeing destination is rated an average of 4.2 out of 5 stars by 1,128 visitors.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Pisa.

You’ll then say farewell to Pisa. 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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