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

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Experience the freedom of the open road in Italy as you embark on an unforgettable 9-day road trip! This experience caters to every traveler, featuring destinations like Pisa, Siena, Rome, and Florence.

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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Driver’s age is 30 - 65
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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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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 immersing yourself in Pisa's charm before embarking on the next leg of your journey.

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.

Treat yourself to a wonderful meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining spot in Pisa. If you're in the mood for something new, try il Mercante, another premier location with a delectable menu. You might also want to book a table at La Ghiotteria. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Jeffer Cocktails & Friends, known for its inviting atmosphere. Le Parisien Wine Bar is another great option if you’re looking for a place to get the night started. Similarly, Las Volta Cocktailbar provides a great setting to enjoy the night away.

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

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Day 2

Day 2

  • Pisa
  • Siena
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Drive 125 km, 2 hours 7 min

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

Today’s itinerary in Pisa covers several incredible sights, including a public square, a monument, and a church. Start your adventure at Knights' Square. This underrated public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Leaning Tower Of Pisa, a must-see monument in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Pisa Cathedral. This intriguing church offers an enriching experience. For a change of pace, head to Piazza Del Duomo, Pisa, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to Battistero Di San Giovanni. These sights offer a fulfilling end to a perfect day.

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.

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

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

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.

Raise your glass to another unforgettable day in Italy!

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Day 3

Day 3

  • Siena
  • 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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Dive into day 3 of your remarkable road trip in Italy. Today you will explore Vatican City, 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 Rome. You’ll stay here for 3 nights.

Begin your sightseeing with Sistine Chapel. This famous chapel is one of the top attractions in the city. Proceed to St. Peter's Basilica, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Saint Peter's Square. This interesting square is a traveler-favorite. Not far away, you’ll find Vatican Museums, another key site on your sightseeing itinerary.

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

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 4

Day 4

  • Rome
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Drive 3 km, 41 min

  • Altare della Patria
  • Roman Forum
  • Colosseum
  • Trastevere
  • Monti
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On day 4 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 2 nights and discover all the best things to see and do in the area.

One of the most iconic places you can visit today in Rome is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby. You can also explore Monti, a neighborhood that offers a glimpse into local life and culture.

Today’s agenda in Rome includes a monument and an archeological site. Altare Della Patria is must-visit monument and a great starting point for the day. Next, continue your journey to Roman Forum, a timeless archeological site, located just a leisurely stroll away. Next, head to Colosseum, an UNESCO world heritage-designated archeological site, 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.

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

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

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar 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 5

Day 5

  • Rome
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Drive 12 km, 1 hour 7 min

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

Make sure to visit Via del Corso, a popular street in Rome. 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.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Piazza Del Popolo is the perfect place to start. This public square is one of the most top-rated places to visit in Rome. Next, head to Pantheon, a wondrous monument, known for its culturally significant features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Navona. This masterful public square is a highly recommended experience. Nearby, you'll also find Castel Sant'angelo. Visit these for an interesting touch to your journey.

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.

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

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

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Day 6

Day 6

  • Rome
  • Florence
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Drive 279 km, 3 hours 44 min

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

Today, you'll explore some of the most beautiful places in Rome, including a monument, a public square, and a park. Start your day with a visit to Trevi Fountain. This globally renowned monument is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Di Spagna, which may be one of the most romantic places you will experience today.

One of the best things about exploring Rome 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 Spanish Steps, a famous public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Villa Borghese.

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.

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

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for 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 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

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.

Don’t miss Oltrarno in Florence today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and history-rich sites. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Basilica Of Santa Croce In Florence is the first of them. Spend some time admiring this culturally significant church before continuing your journey. Piazza Della Signoria is your next stop. This famous public square is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Uffizi Gallery. This historic art gallery is a sight to behold. To round off your sightseeing experience, visit Ponte Vecchio.

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 you explore more of Florence, 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.

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.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 8

Day 8

  • Florence
  • Pisa
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Drive 91 km, 1 hour 50 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Galleria dell'Accademia
  • David
  • piazzale Michelangelo
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On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Cathedral Of Santa Maria Del Fiore. This UNESCO world heritage-listed church is a highlight of any visit in the city. Then, enjoy Central Market, another instagrammable attraction that never fails to captivate visitors. Next, head over to Galleria Dell'accademia, one of the city’s most locally renowned attractions, known for its detailed features.

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.

Indulge in a memorable dining experience at one of Pisa's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Explore the vibrant nightlife at Bar Mocambo after your meal, a hub for lively evenings and memorable moments. Or, head to Tree for a great selection of flavorful drinks and a charming setting. Furthermore, Chupiteria is perfect for those looking to extend their night with a touch of local flavor.

Celebrate another amazing day of your road trip adventure 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, begin at Palazzo Gambacorti. This curiosity-inducing palace is a popular place to see in the city.

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.

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 in the mood to try something new, consider Ristorante alle Bandierine, another top spot with a mouthwatering 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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