Relaxed 11-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
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Description
Explore Italy and discover its unique charm on this 11-day relaxed road trip through Pisa, Florence, Castellina in Chianti, Siena, San Gimignano, Corniglia, Vernazza, Lucca, Montecatini Terme, Vinci, and Fucecchio. Delight in a stress-free journey that focuses on exploration through the country's most captivating landscapes.
This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Pisa, Florence, Castellina in Chianti, Siena, San Gimignano, Corniglia, Vernazza, Lucca, Montecatini Terme, Vinci, and Fucecchio. Make yourself at home at top-rated hotels and stay 2 nights in Pisa and 8 nights in Florence. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.
Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Pisa, you’ll collect your rental car of choice. From there, you’ll begin your 11-day journey across Italy and discover its unique culture, history, and diverse scenery.
Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.
We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Ponte Vecchio. Another highlight of this self-drive tour is the captivating Leaning Tower Of Pisa.
Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Piazza Del Duomo, Pisa. With this travel plan, you could also soak in the atmosphere of the memorable Piazzale Michelangelo. Get close to the spectacular Cathedral Of Santa Maria Del Fiore and the wonderful Piazza Della Signoria. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.
Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.
Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.
This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 10 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 11 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.
This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.
Spend an amazing 11-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Italy today!
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Day 1
- Pisa - Arrival day
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- Knights' Square
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Your relaxed road trip through Italy starts when you reach the incredible city of Pisa, where you'll stay for 1 night. You'll pick up your rental car in Pisa and begin your adventure in Italy.
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.
Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Pisa. Make yourself at home and enjoy some downtime before heading out again.
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.
If you feel like it, head out to a bar to celebrate another fantastic day in Pisa and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.
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 as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Pisa as you soak in the city’s unique vibe.
Day 2
- Pisa
- Florence
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Drive 90 km, 1 hour 59 min
- Leaning Tower of Pisa
- Piazza del Duomo, Pisa
- Central Market
- Galleria dell'Accademia
- Cathedral of Santa Maria del Fiore
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Day 2 of your relaxed road trip across the beautiful country of Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!
Today's adventure in Pisa promises more breathtaking discoveries and enriching experiences! Begin at Leaning Tower Of Pisa. This culturally significant monument is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another UNESCO world heritage-listed attraction that never fails to captivate visitors. Next, head over to Central Market, one of the city’s most locally renowned attractions, known for its visually striking features.
If you’re looking for more, spend time soaking in the atmosphere of Galleria Dell'accademia. This eye-catching art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Cathedral Of Santa Maria Del Fiore, an astonishing church, and take a stroll around the area.
Continue your laid-back road trip exploration of the best attractions in Italy at Florence. Select from top hotels and accommodations in the city to recharge and rejuvenate.
Exploring the food culture in Florence offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.
Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.
Hang out and unwind at some of the top bars in Florence.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.
Toast to another unforgettable and relaxing road trip adventure in Italy!
Day 3
- Florence
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Drive 6 km, 49 min
- Ponte Vecchio
- piazza della Signoria
- Uffizi Gallery
- piazzale Michelangelo
- Oltrarno
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Day 3 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.
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 fun adventures, romantic experiences, and scenic views. 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. Ponte Vecchio is the first of them. Spend some time admiring this respected historical landmark before continuing your journey. Piazza Della Signoria is your next stop. This impressive 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 romantic art gallery is a sight to behold. To round off your sightseeing experience, visit Piazzale Michelangelo.
Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Florence. There are so many fun and eye-opening activities to try out in Florence that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Florence to find the best options for you!
Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.
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.
If you feel like it, head out to a bar to celebrate another fantastic day in Florence and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.
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.
Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!
Day 4
- Florence
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Drive 101 km, 2 hours 6 min
- Poggio Amorelli
- Tumulo di Montecalvario
- Rocca di Castellina in Chianti
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On day 4 of your relaxed road trip across Italy, you’ll explore the area around Florence, where you’ll be staying for another 6 nights. With so many fun and inspiring experiences to offer, a tour of Florence will make you fall even more in love with the city and uniqueness of Italy.
Today’s agenda in Florence includes a winery, an archeological site, and a castle. Poggio Amorelli is must-visit winery and a great starting point for the day. Next, continue your journey to Tumulo Di Montecalvario, an often recommended archeological site, located just a leisurely stroll away. Next, head to Rocca Di Castellina In Chianti, a respected castle, also available for your discovery today.
When you’re done exploring for the day, you’ll return to Florence and your accommodation.
Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Florence, explore the city like a local by trying out the best restaurants in the area.
Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.
If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.
Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.
Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!
Day 5
- Florence
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Drive 149 km, 2 hours 58 min
- Palazzo Salimbeni
- piazza del Campo
- Siena Cathedral
- Basilica of San Domenico
- Fortezza Medicea
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On day 5 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in Siena destinations, just outside of the city. You still have 5 nights left in Florence. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.
Discover a day packed with family-friendly attractions, photo-friendly spots, and history-rich sites in Florence. Begin your sightseeing with Palazzo Salimbeni. This often recommended palace is one of the top attractions in the city. Proceed to Piazza Del Campo, 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 Siena Cathedral. This interesting church is a traveler-favorite. Not far away, you’ll find Basilica Of San Domenico, another key site on your sightseeing itinerary. Fortezza Medicea (siena) is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.
Enjoy a lovely dining experience at Tijuana, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Djària - American Bar, 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 The Florence Irish Pub. It’s yet another ideal choice to enhance your time in Florence tonight.
After dinner, it’s time to fall in love with the amazing nightlife in Florence and unwind at some of the best bars in the city.
Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!
Day 6
- Florence
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Drive 116 km, 2 hours 13 min
- Porta San Giovanni
- SanGimignano1300
- Town Hall, Picture Gallery and Great Tower
- Piazza del Duomo, San Gimignano
- Parco della Rocca
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Your laid-back and relaxed road trip in Italy continues on day 6, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Florence and beyond. With 4 nights left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.
Start by visiting Porta San Giovanni, a prime spot to begin your journey. This picture-perfect monument is sure to impress. Next on your list is Sangimignano1300, another must-visit landmark and locally appreciated museum renowned for its photogenic features.
While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Palazzo Comunale, Pinacoteca, Torre Grossa. This culturally significant museum is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Piazza Del Duomo, a locally appreciated public square. Nearby, you'll also find Parco Della Rocca, ready to add charm to your journey.
When you’re done exploring for the day, you’ll return to Florence and your accommodation.
Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.
Enjoy a lovely meal at Ristorante Buca Niccolini, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Essenziale is another top choice with a popular menu. You could also check for a table at Ristorante La Grotta Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.
Hang out and unwind at some of the top bars in Florence.
Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!
Day 7
- Florence
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Drive 367 km, 5 hours 20 min
- Cinque Terre National Park
- Ruins of Doria Tower
- Church of St. Margaret of Antioch
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On day 7 of your relaxed road trip across Italy, you’ll explore the area around Florence, where you’ll be staying for another 3 nights. With so many fun and inspiring experiences to offer, a tour of Florence will make you fall even more in love with the city and uniqueness of Italy.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most notable attractions included on the itinerary is Cinque Terre National Park. This eye-catching national park will help you start your sightseeing on top. Then, take a leisurely stroll to Ruins Of Doria Tower and learn what makes this history-steeped monument unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the underrated Church Of St. Margaret Of Antioch.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.
Dine in style at Cibrèo Caffè, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Le Volte Firenze boasts a menu that's sure to impress. Also, be sure to check out Ristorante Romantico il Paiolo. Known as a local hotspot, it’s a great choice for tonight in Florence.
A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Florence.
Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across Italy.
Day 8
- Florence
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Drive 175 km, 2 hours 43 min
- Walls of Lucca
- Piazza Napoleone
- St Martin Cathedral
- Guinigi Tower
- Piazza dell'Anfiteatro
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On day 8 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in Lucca destinations, just outside of the city. You still have 2 nights left in Florence. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.
Florence is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Mura Di Lucca, an increasingly popular historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Piazza Napoleone, enchanting visitors with its enchanting appeal. Continue your exploration at St Martin Cathedral. This church is one of the city’s most up-and-coming 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 Guinigi Tower. After exploring the monument, head to the well-known Piazza Dell'anfiteatro.
When you’re done exploring for the day, you’ll return to Florence and your accommodation.
Exploring the food culture in Florence offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.
Treat yourself to a delicious dinner at Osteria Tripperia Il Magazzino, an excellent option for tonight's dining. Looking for something different? Ristorante La Spada offers a tantalizing alternative with its diverse menu. And don’t miss Osteria Vecchio Cancello. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.
As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.
Toast to another unforgettable and relaxing road trip adventure in Italy!
Day 9
- Florence
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Drive 114 km, 1 hour 59 min
- Parco delle Terme
- Montecatini Terme centro
- Church of Saint Mary of the Assumption
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Your laid-back and relaxed road trip in Italy continues on day 9, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Florence and beyond. With 1 night left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.
Florence is brimming with adventures. Today’s wonderful stops include a park, a spa, and a church. Begin your sightseeing adventure at the beloved Parco Delle Terme and allow yourself time to explore. Just a short distance away you'll find your next stop, Montecatini Terme Centro, a romantic spa that draws visitors from far and near.
Continue your journey to Church Of Saint Mary Of The Assumption, one of the town’s most often recommended spots that you shouldn’t miss.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.
Make sure to reserve a table at Hotel Lungarno, 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 Residence la Contessina, 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 Ristorante Paoli, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Before calling it a day, visit one of the best bars in Florence. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.
A leisurely self-drive holiday in Montecatini Terme can’t get any better than this! Toast to another amazing day in Italy!
Day 10
- Florence
- Pisa
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Drive 120 km, 2 hours 11 min
- Leonardo da Vinci museum
- Padule di Fucecchio
- Porto delle Morette
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Day 10 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the town of Vinci. By the end of the day, you’ll drive in the direction of the city of Pisa, where you’ll stay at a top-rated hotel of your choice for 1 night.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Leonardo Da Vinci Museum. This curiosity-inducing museum provides an insightful glimpse into the town's identity. Next, discover Padule Di Fucecchio, an enchanting nature reserve, promising a delightful encounter.
Continue your sightseeing with a visit to Porto Delle Morette, a locally appreciated park.
After a day of exploration, relax at one of the top hotels or accommodations in Pisa. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.
Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Pisa, explore the city like a local by trying out the best restaurants in the area.
Don’t miss out on dining at Ristorante Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider La Locanda Dei Pisani Doc Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.
After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.
After enjoying a fulfilling meal, continue your evening at Bar Mocambo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tree offers a welcoming atmosphere for easing into the nightlife. Similarly, Chupiteria provides an excellent environment for a relaxed and enjoyable evening.
Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!
Day 11
- Pisa - Departure day
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- Palazzo Gambacorti
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Day 11 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Pisa.
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.
If you're up for some more sightseeing, we recommend visiting Palazzo Gambacorti, a standout palace before you head out.
Unwind and look back at the past 11 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Pisa or just grab something light to keep you going.
Give yourself enough time to wave goodbye to Pisa and begin your journey home. The unforgettable experiences you’ve collected along your 11-day relaxed road trip in Italy is a story you will tell for the rest of your life.
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