12-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Siena, and Rome
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Experience the freedom of the open road in Italy as you embark on an unforgettable 12-day road trip! This experience caters to every traveler, featuring destinations like Pisa, Florence, Greve in Chianti, Castellina in Chianti, Siena, San Gimignano, Castelnuovo dell'Abate, Montalcino, Pienza, Castiglione d'Orcia, Rome, and Orvieto.
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, 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 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, 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, 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
- Pisa - Arrival day
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- “Tuttomondo” (Keith Haring)
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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 “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.
Enjoy a delicious meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.
Cap off your dinner by heading to Jeffer Cocktails & Friends, ideal for a leisurely evening with a drink in hand. Le Parisien Wine Bar is another bar that offers an enjoyable setting. Similarly, Las Volta Cocktailbar is also a popular place to go on a night out, perfect for relaxing and socializing.
Raise a toast to the start of your 12-day road trip in Italy!
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
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 vibrant destinations - Pisa and Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 3 nights here for some well-deserved relaxation.
Pisa is brimming with adventures. Today’s wonderful stops include a public square, a monument, a cemetery, an art gallery, a church and much more! Begin your sightseeing adventure at the beloved Knights' Square and allow yourself time to explore. Just a short distance away you'll find your next stop, Leaning Tower Of Pisa, an UNESCO world heritage-designated monument that draws visitors from far and near.
Continue your journey to Piazza Del Duomo, Pisa, one of the city’s most wondrous spots that you shouldn’t miss. Another great site to visit is the up-and-coming Campo Santo. When you're finished at the cemetery, Galleria Dell'accademia awaits your visit. This art gallery is a detailed highlight on today's itinerary. Last up is a church - the widely recognized Cathedral Of Santa Maria Del Fiore.
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.
After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.
Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.
Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.
Savor another day of unforgettable experiences in Italy!
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
Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.
Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Florence. Your adventure starts at Piazzale Michelangelo, a widely recognized local hot spot. Another notable attraction to explore is Basilica Of Santa Croce In Florence. This popular church is known for its enchanting appeal.
After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Della Signoria. This visually striking public square offers a fascinating experience that many visitors find memorable. Uffizi Gallery is also worth visiting, along with Ponte Vecchio. These standout landmarks offer unique experiences that add to the day’s enjoyment.
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.
Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.
After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.
Savor another day of unforgettable experiences in Italy!
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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At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most worthwhile attractions included on the itinerary is Castle Of Verrazzano. This instagrammable castle will help you start your sightseeing on top. Then, take a leisurely stroll to Tumulo Di Montecalvario and learn what makes this eye-catching archeological site unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Rocca Di Castellina In Chianti.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
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.
Make sure to reserve a table at Ristorante Buca Mario, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Agricola Toscana, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.
Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!
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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Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 3 nights.
Discover a day packed with fun adventures, romantic experiences, and scenic views in Florence. Begin your sightseeing with Siena Cathedral. This interesting church is one of the top attractions in the city. Proceed to Pubblico Palace, another must-visit attraction.
As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Del Campo. This extraordinary public square is a traveler-favorite. Not far away, you’ll find Tower Of Mangia, another key site on your sightseeing itinerary.
When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and spend some time relaxing before you head out to tour the city.
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.
To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.
Say good night to Siena and look forward to another great day of your road trip in Italy!
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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Wake up to day 6 of your extraordinary road trip in Italy. With 2 nights left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!
Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Rocca Di Montestaffoli. This visually striking castle is sure to ignite your curiosity. Next, dive into the culturally significant features of Palazzo Comunale, Pinacoteca, Torre Grossa, a must-visit museum in the village.
In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Piazza Del Duomo, a curiosity-inducing public square.
When you’re done exploring for the day, you’ll return to Siena and your accommodation.
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.
Have a fantastic dining experience at Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.
Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start. You could also check out Bar Pinacoteca, offering a different kind of charm. A last recommendation for the day is San Paolo Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.
Raise your glass and celebrate another amazing day of your road trip in Italy!
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 start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Castelnuovo dell'Abate, Montalcino, Pienza, and Castiglione d'Orcia. You still have 1 night left in Siena.
Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Siena. Begin your sightseeing with Abbey Of Sant'antimo. This often recommended monastery is one of the top attractions in the village. Proceed to Fortress Of Montalcino, 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 Palazzo Piccolomini, Pienza. This increasingly popular palace is a traveler-favorite. Not far away, you’ll find Rocca D'orcia, another key site on your sightseeing itinerary.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Siena.
As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.
Don’t miss out on dining at Ristorante San Desiderio, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Le Logge, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.
Get a good night's sleep and look forward to another great day on the road in Italy!
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
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On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 3 nights.
Siena is home to plenty of attractions that offer fun adventures, romantic experiences, and natural wonders! Start at Villa Borghese, an impressive park that is worthwhile a visit in the city. Nearby, you’ll find Spanish Steps, enchanting visitors with its respected appeal. Continue your exploration at Piazza Di Spagna. This public square is one of the city’s most globally renowned spots.
Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Trevi Fountain. After exploring the monument, head to the iconic Pantheon.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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 an authentic adventure.
Enjoy a lovely dining experience at La Bottega Roma, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Pasta In Corso, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Trattoria Vecchia Roma. It’s yet another ideal choice to enhance your time in Rome tonight.
If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.
Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!
Day 9
- Rome
- More
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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Day 9 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.
Make sure to visit Trastevere, a popular neighborhood 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. You can also explore Via del Corso today, a street that’s well worth a visit.
Begin your adventure at Piazza Del Popolo. This is a widely recognized public square you should not miss. Another must-see is St. Peter's Basilica, a wondrous major basilica in Rome.
When you’re ready for the next sight, head to Sistine Chapel. From there, take a leisurely stroll to Vatican Museums, another of the city’s world-famous attractions.
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.
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.
Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 10
- Rome
- More
Drive 9 km, 1 hour 19 min
- Colosseum
- Arch of Constantine
- Roman Forum
- Campo de' Fiori
- Piazza Navona
- Castel Sant'Angelo
- More
On day 10 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.
Rome is brimming with adventures. Today’s wonderful stops include an archeological site, a monument, a public square, a castle and much more! Begin your sightseeing adventure at the world-famous Colosseum and allow yourself time to explore. Just a short distance away you'll find your next stop, Arch Of Constantine, a masterful monument that draws visitors from far and near.
Continue your journey to Roman Forum, one of the city’s most iconic spots that you shouldn’t miss. Another great site to visit is the top-rated Campo De' Fiori. When you're finished at the public square, Piazza Navona awaits your visit. This public square is a grand highlight on today's itinerary. Last up is a castle - the top-rated Castel Sant'angelo.
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 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.
Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.
Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 11
- Rome
- Pisa
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Drive 371 km, 4 hours 31 min
- Orvieto Cathedral
- Orvieto subterranea
- Torre del Moro Orvieto
- Pozzo della Cava
- More
On day 11 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 Orvieto. In the evening, you’ll end up in Pisa, where you will stay for 1 night.
Get ready to discover some of the most iconic wonders in Rome, including a church, a cave system, a monument, a cave and much more! Start your day at Orvieto Cathedral. This majestic church is an interesting place to see in Rome. Then, wander over to Orvieto Underground. If photogenic sites excite you, this cave system will be right up your alley. Nearby, you’ll also find Torre Del Moro Orvieto. This historic monument is a favorite among visitors.
Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pozzo Della Cava is an up-and-coming spot in the town that will captivate you with its unique charm.
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 and reflect on the day's adventures.
Dine in style at Ristorante Capodimonte Pisa, a top recommendation for dinner tonight. Or, for a change of pace, La Locanda Dei Pisani Doc Pisa boasts a menu that's sure to impress. Also, be sure to check out Baribaldi Pisa. Known as a local hotspot, it’s a great choice for tonight in Pisa.
Round off your dining experience by visiting Bar Mocambo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Tree, a bar catering to every mood and preference. Chupiteria likewise offers a unique atmosphere, perfect for a memorable night out.
Celebrate another amazing day of your road trip adventure in Italy!
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. 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.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Pisa's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Pisa.
Dine in style at Restaurant -Pizzeria Il Mio Capriccio, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante alle Bandierine boasts a menu that's sure to impress.
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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