11-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Siena, Rome, and Naples
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Explore the best of Italy on a 11-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Pisa, Florence, Siena, San Gimignano, Rome, Naples, Pompei, and Lucca. 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, 2 nights in Florence, 2 nights in Siena, 2 nights in Rome, and 2 nights in Naples. 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, Siena, San Gimignano, Rome, Naples, Pompei, and Lucca, 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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- Knights' Square
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Welcome to Pisa, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night 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 Knights' Square, 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 savoring a delicious meal, step into the vibrant nightlife at Jeffer Cocktails & Friends, where the evening is just getting started. In the same way, Le Parisien Wine Bar offers a unique charm perfect for experiencing the local bar scene in Pisa. Las Volta Cocktailbar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Raise a toast to the start of your 11-day road trip in Italy!
Day 2
- Pisa
- Florence
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Drive 93 km, 1 hour 50 min
- Leaning Tower of Pisa
- Angelo Caduto
- Piazza del Duomo, Pisa
- Battistero di San Giovanni
- Pisa Cathedral
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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 1 vibrant destinations - Pisa. 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.
Start your day with a visit to Leaning Tower Of Pisa. This iconic monument is a must-visit in the city.
One of the best things about exploring Pisa 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 Piazza Del Duomo, Pisa, a globally renowned public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Battistero Di San Giovanni and Pisa Cathedral.
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.
As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.
Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 3
- Florence
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Drive 4 km, 1 hour 6 min
- piazzale Michelangelo
- Uffizi Gallery
- Ponte Vecchio
- piazza della Signoria
- Cathedral of Santa Maria del Fiore
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On day 3 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.
Today’s itinerary in Florence covers several incredible sights, including an observation deck, an art gallery, a historical landmark, a public square, a church and much more! Start your adventure at Piazzale Michelangelo. This top-rated observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Uffizi Gallery, a must-see art gallery 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 Ponte Vecchio. This timeless historical landmark offers an enriching experience. For a change of pace, head to Piazza Della Signoria, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Cathedral Of Santa Maria Del Fiore. These sights offer a fulfilling end to a perfect day.
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 Florence. 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 Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.
Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.
Savor another day of unforgettable experiences in Italy!
Day 4
- Florence
- Siena
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Drive 77 km, 1 hour 38 min
- Fortezza Medicea
- Piazza del Duomo
- Siena Cathedral
- piazza del Campo
- Tower of Mangia
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On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.
Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, scenic views, and picturesque spots. Start at Fortezza Medicea (siena), an up-and-coming monument in the city. Then, head to Piazza Del Duomo and soak in the ambiance of this romantic public square.
There are many interesting places to see in Florence, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most popular enchanting spots of interest. After exploring the church, visit the astonishing Piazza Del Campo. Not far away, you'll also find Tower Of Mangia. This monument is a culturally significant highlight in Florence.
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.
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.
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 your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 5
- Siena
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Drive 83 km, 1 hour 48 min
- Porta San Giovanni
- Piazza del Duomo, San Gimignano
- Town Hall, Picture Gallery and Great Tower
- Parco della Rocca
- Chiesa di Sant'Agostino
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Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in San Gimignano.
Get ready to discover some of the most iconic wonders in Siena, including a monument, a public square, a museum, a park, a church and much more! Start your day at Porta San Giovanni. This breathtaking monument is a locally appreciated place to see in Siena. Then, wander over to Piazza Del Duomo. If visually striking sites excite you, this public square will be right up your alley. Nearby, you’ll also find Palazzo Comunale, Pinacoteca, Torre Grossa. This culturally significant museum is a favorite among visitors.
Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Parco Della Rocca is a curiosity-inducing spot in the village that will captivate you with its unique charm. When you’re done at the park, don’t forget to check out the culturally significant Chiesa Di Sant'agostino. Take a moment to appreciate the fascinating details of this beloved church.
When you’re done exploring for the day, you’ll return to Siena and your accommodation.
After a day of adventure, treat yourself to an exquisite dinner at one of Siena's best restaurants.
Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.
Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand. Bar Pinacoteca is another bar that offers an enjoyable setting. Similarly, San Paolo Pub is also a popular place to go on a night out, perfect for relaxing and socializing.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 6
- Siena
- Rome
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Drive 242 km, 3 hours 38 min
- Colosseum
- Roman Forum
- Trevi Fountain
- Piazza Navona
- Pantheon
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On day 6 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 Rome. In the evening, you’ll end up in Rome, where you will stay for 2 nights.
Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Colosseum is the perfect place to start. This archeological site is one of the most world-famous places to visit in Siena. Next, head to Roman Forum, an iconic archeological site, known for its UNESCO world heritage-designated 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 Trevi Fountain. This masterful monument is a highly recommended experience. Nearby, you'll also find Piazza Navona and Pantheon. Visit these for an interesting touch to your journey.
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.
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.
Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.
After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio 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.
Day 7
- Rome
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Drive 11 km, 44 min
- St Peter's Basilica
- Piazza di Spagna
- Trastevere
- Via del Corso
- Via dei Condotti
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On day 7 of your road trip, you’ll start and end your day in Rome, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Vatican City and Rome. You still have 1 night left in Rome.
A visit to Trastevere in Vatican City is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights. Don’t forget to check out Via del Corso as well, a street that adds another layer to your exploration.
Just a short distance away you'll find your next stop, Piazza Di Spagna, a majestic public square that draws visitors from far and near.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.
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.
Raise your glass to another unforgettable day in Italy!
Day 8
- Rome
- Naples
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Drive 233 km, 3 hours 21 min
- Naples National Archaeological Museum
- Ovo Castle
- Castel Nuovo
- piazza del Plebiscito
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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 Naples. At the end of the day, you will enjoy the comforts of a top-rated hotel in Naples, which will be your home away from home for 2 nights.
Rome is home to plenty of attractions that offer fun adventures, picturesque spots, and historic treasures! Start at Naples National Archaeological Museum, an interesting museum that is worthwhile a visit in the city. Nearby, you’ll find Ovo Castle, enchanting visitors with its history-steeped appeal. Continue your exploration at Castel Nuovo. This castle is one of the city’s most captivating spots.
Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Del Plebiscito.
At the end of the day, you will drive to Naples, 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 Naples's best restaurants.
Enjoy a delicious meal at L'Oca Nera Irish Pub, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Mimì alla Ferrovia, another top spot with a mouthwatering menu. You might also want to secure a reservation at Spuzzulè Winebar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.
Explore the vibrant nightlife at Happening Cocktail Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Shanti Art Musik Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Gran Caffè Gambrinus is perfect for those looking to extend their night with a touch of local flavor.
Savor another day of unforgettable experiences in Italy!
Day 9
- Naples
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Drive 54 km, 1 hour 27 min
- Archaeological Park of Pompeii
- Basilica
- Lupanar des esclaves
- Teatro Grande
- Amphitheatre of Pompeii
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On day 9 of your road trip in Italy, you’ll start and end your day in Naples, but spend the day exploring what’s beyond the city. Since you will return to Naples for 1 night more, there’s no need to rush. Experience Pompei to the fullest today with this curated day itinerary!
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Naples allows for both. Start by heading to Archaeological Park Of Pompeii. This notable archeological site provides an insightful glimpse into the town's identity. Next, discover Basilica, an UNESCO world heritage-listed archeological site, promising a delightful encounter.
Continue your sightseeing with a visit to Lupanare Di Pompei, an up-and-coming archeological site. When you’re done, don’t forget to make a stop at the increasingly popular Teatro Grande. Round off your day at Amphitheatre Of Pompeii, another gem in Naples with picture-perfect features to discover.
When you’re done exploring for the day, you’ll return to Naples and your accommodation.
As you explore more of Naples, 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.
Enjoy a lovely meal at Antica Pizzeria Di Matteo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Mercure Napoli Centro Angioino is another top choice with a popular menu. You could also check for a table at La Lazzara Trattoria e Pizzeria. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Naples tonight.
Extend your evening after a delightful meal by visiting Archivio Storico - Cocktail Bar & Wonderfood, which offers the perfect atmosphere for a night out. Moreover, Archeobar is another popular option for a drink or two. Likewise, Babette Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 10
- Naples
- Pisa
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Drive 576 km, 6 hours 13 min
- Guinigi Tower
- Piazza dell'Anfiteatro
- St Martin Cathedral
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Dive into day 10 of your remarkable road trip in Italy. Today you will explore Lucca, 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 Pisa. You’ll stay here for 1 night.
Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Guinigi Tower. This intriguing monument is a visually striking place to see in Naples. Continue your discovery at Piazza Dell'anfiteatro, a romantic public square with stories to tell.
As you stroll around Naples, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to St Martin Cathedral. This underrated church offers a monumental encounter with Naples. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Naples.
When you’re done exploring for the day, you’ll drive to your hotel in Pisa. Check in and spend some time relaxing before you head out to tour the city.
Indulge in a memorable dining experience at one of Pisa's most popular restaurants, and connect with friendly locals for an authentic adventure.
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 your meal, keep the night alive at a bar like Bar Mocambo, known for its lively atmosphere. Tree is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Chupiteria offers an excellent atmosphere for those looking to amp up the evening.
Raise your glass to another unforgettable day in Italy!
Day 11
- Pisa - Departure day
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- Palazzo Gambacorti
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Day 11 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 history-steeped palace before you head out.
On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Pisa.
Savor the flavors at Restaurant -Pizzeria Il Mio Capriccio, a top pick for dinner tonight. Alternatively, Ristorante alle Bandierine beckons with its unique menu offerings.
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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