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

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Explore the best of Italy on a 9-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Pisa, Siena, Rome, and Florence. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

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. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of St. Peter's Basilica.

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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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
“Tuttomondo” (Keith Haring)
Knights' SquareLeaning Tower of PisaPisa CathedralPiazza del Duomo, PisaBattistero di San Giovanni
Sistine ChapelSt Peter's BasilicaSaint Peter's SquareVatican Museums
Altare della PatriaRoman ForumColosseumTrastevereMonti
piazza del PopoloPantheonPiazza NavonaCastel Sant'AngeloVia del Corso
Trevi FountainPiazza di SpagnaSpanish StepsVilla Borghese

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Day 1

Day 1

  • Pisa - Arrival day
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  • “Tuttomondo” (Keith Haring)
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Say hello to Pisa! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Pisa for 1 night before you continue your adventure!

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 “tuttomondo” (keith Haring), or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Pisa. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Jeffer Cocktails & Friends, a well-loved spot among locals and tourists. Or, head to Le Parisien Wine Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Las Volta Cocktailbar, another top-rated place in the area.

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

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Day 2

Day 2

  • Pisa
  • Siena
  • More

Drive 125 km, 2 hours 7 min

  • Knights' Square
  • Leaning Tower of Pisa
  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Battistero di San Giovanni
  • More

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Pisa, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Siena. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Pisa, featuring family-friendly attractions, breathtaking views, and photo-friendly spots. Start at Knights' Square, an often recommended public square in the city. Then, head to Leaning Tower Of Pisa and soak in the ambiance of this historic monument.

There are many interesting places to see in Pisa, and when you are ready for more, go to Pisa Cathedral. This is one of the city’s most frequently visited picture-perfect spots of interest. After exploring the church, visit the iconic Piazza Del Duomo, Pisa. Not far away, you'll also find Battistero Di San Giovanni. This church is a stunning highlight in Pisa.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day 3

Day 3

  • Siena
  • Rome
  • More

Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
  • More

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Vatican City. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Start your day with a visit to Sistine Chapel. This spectacular chapel is a must-visit in the city.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Saint Peter's Square, a notable square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Vatican Museums.

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.

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

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of mediterranean and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative and innovative 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 Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean and creative menu. With a 2-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 Rome.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 4

Day 4

  • Rome
  • More

Drive 3 km, 41 min

  • Altare della Patria
  • Roman Forum
  • Colosseum
  • Trastevere
  • Monti
  • More

Day 4 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

A top thing to do today is to explore Trastevere, a must-see neighborhood in Rome. It's the perfect starting point for touring the top attractions in the area. You can also visit Monti, an ideal neighborhood for continued sightseeing.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Altare Della Patria, an interesting monument in the city. Then, head to Roman Forum and soak in the ambiance of this historic archeological site.

There are many interesting places to see in Rome, and when you are ready for more, go to Colosseum. This is one of the city’s most world-famous breathtaking spots of interest.

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

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

Make sure to reserve a table at RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 5

Day 5

  • Rome
  • More

Drive 12 km, 1 hour 7 min

  • piazza del Popolo
  • Pantheon
  • Piazza Navona
  • Castel Sant'Angelo
  • Via del Corso
  • More

Day 5 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Via del Corso is a street that stands out as one of the must-see places in Rome. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the famous Piazza Del Popolo, a romantic public square in Rome. Next, go to Pantheon.

After visiting Piazza Del Popolo and Pantheon, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Piazza Navona. This symbolic public square offers a unique experience. Castel Sant'angelo is another noteworthy attraction worthwhile a visit.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. 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 Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Unwind after your meal by stepping into The Apartment Bar Roma. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Hassler Roma offers a dynamic and energetic atmosphere for a glass or two.

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

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Day 6

Day 6

  • Rome
  • Florence
  • More

Drive 279 km, 3 hours 44 min

  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • 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.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most globally renowned attractions included on the itinerary is Trevi Fountain. This enchanting monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Di Spagna and learn what makes this enchanting public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the widely recognized Spanish Steps. After exploring the public square, head to Villa Borghese. This famous park is a highlight in Rome.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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

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Day 7

Day 7

  • Florence
  • More

Drive 1 km, 25 min

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

On day 7 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Make sure to visit Oltrarno, a popular neighborhood in Florence. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Today’s agenda in Florence includes a church, a public square, an art gallery, a historical landmark and much more! Basilica Of Santa Croce In Florence is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Della Signoria, a widely recognized public square, located just a leisurely stroll away. Next, head to Uffizi Gallery, an instagrammable art gallery, also available for your discovery today.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities 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 delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day in Italy!

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Day 8

Day 8

  • Florence
  • Pisa
  • More

Drive 91 km, 1 hour 50 min

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

On day 8 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 Florence. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Florence is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Cathedral Of Santa Maria Del Fiore, a widely recognized church that is worthwhile a visit in the city. Nearby, you’ll find Central Market, enchanting visitors with its visually striking appeal. Continue your exploration at Galleria Dell'accademia. This art gallery is one of the city’s most popular spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit David. After exploring the statue, head to the extraordinary Piazzale Michelangelo.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

As you explore more of Pisa, 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.

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Locanda Dei Pisani Doc Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Baribaldi Pisa, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Mocambo, a well-loved spot among locals and tourists. Or, head to Tree. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Chupiteria, another top-rated place in the area.

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 9

Day 9

  • Pisa - Departure day
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  • Palazzo Gambacorti
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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.

If you're up for some more sightseeing, we recommend visiting Palazzo Gambacorti, a heritage-rich palace before you head out.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

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

If you're eager to try something different, consider Ristorante alle Bandierine, another top spot with a tantalizing menu.

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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