Relaxed 11-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
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Experience Italy like never before on this 11-day relaxed road trip, traversing through Pisa, Florence, Castellina in Chianti, Siena, San Gimignano, Corniglia, Vernazza, Lucca, Montecatini Terme, Vinci, and Fucecchio. This self-drive vacation offers a tranquil journey through the heart-stopping beauty found in Italy.
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.
As afternoon approaches, head to your chosen hotel in Pisa. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.
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.
Don’t miss out on dining 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.
Experience the amazing nightlife in Pisa and unwind at the coolest bars in the city.
After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Jeffer Cocktails & Friends, a well-loved spot among locals and tourists. Or, head to Le Parisien Wine Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Las Volta Cocktailbar, another top-rated place in the area.
Raise a toast 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 self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Florence for 8 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.
Brace yourself for today’s incredible lineup of attractions in Pisa, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Leaning Tower Of Pisa, a world-famous monument in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this breathtaking public square.
There are many interesting places to see in Pisa, and when you are ready for more, go to Central Market. This is one of the city’s most interesting photogenic spots of interest. After exploring the food market, visit the captivating Galleria Dell'accademia. Not far away, you'll also find Cathedral Of Santa Maria Del Fiore. This church is an inviting highlight in Pisa.
After a day of exploration, relax at one of the top hotels or accommodations in Florence. 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 Florence, explore the city like a local by trying out the best restaurants in the area.
Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San 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.
Experience the amazing nightlife in Florence and unwind at the coolest bars in the city.
Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.
Raise your glass to celebrate another day of your laid-back and relaxed road trip experience 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 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!
A visit to Oltrarno in Florence 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.
Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Ponte Vecchio, a wondrous historical landmark in the city. Then, head to Piazza Della Signoria and soak in the ambiance of this history-steeped public square.
There are many interesting places to see in Florence, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most famous romantic spots of interest. After exploring the art gallery, visit the famous 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!
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.
Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.
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.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.
Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across 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.
Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Poggio Amorelli. This underrated winery is one of the top attractions in the village. Proceed to Tumulo Di Montecalvario, 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 Rocca Di Castellina In Chianti. This often recommended castle is a traveler-favorite.
When you’re done exploring for the day, you’ll return to Florence and your accommodation.
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.
Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.
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.
Start by visiting Palazzo Salimbeni, a prime spot to begin your journey. This history-steeped palace is sure to impress. Next on your list is Piazza Del Campo, another must-visit landmark and top-rated public square renowned for its UNESCO world heritage-listed 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 Siena Cathedral. This enchanting church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Basilica Of San Domenico, an increasingly popular church. Nearby, you'll also find Fortezza Medicea (siena), ready to add charm to your journey.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
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 Tijuana, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Djària - American Bar is another top choice with a popular menu. You could also check for a table at The Florence Irish Pub. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.
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.
Raise your glass and relax after another big day of your leisurely paced road trip 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.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most beloved attractions included on the itinerary is Porta San Giovanni. This historic monument will help you start your sightseeing on top. Then, take a leisurely stroll to Sangimignano1300 and learn what makes this photogenic museum unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the increasingly popular Palazzo Comunale, Pinacoteca, Torre Grossa. After exploring the museum, head to Piazza Del Duomo. This up-and-coming public square is a highlight in Florence. As your day continues, stop by Parco Della Rocca, known for its visually striking features.
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.
Savor the flavors at Ristorante Buca Niccolini, a top pick for dinner tonight. Alternatively, Essenziale beckons with its unique menu offerings. Also, consider Ristorante La Grotta Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.
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.
Grab a drink and enjoy every passing minute of this night of your 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.
Today’s route brings fun adventures, romantic experiences, and natural wonders. The first attraction of today is Cinque Terre National Park. This notable national park is an eye-catching place to see in Florence. Continue your discovery at Ruins Of Doria Tower, an enchanting monument with stories to tell.
As you stroll around Florence, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Church Of St. Margaret Of Antioch. This up-and-coming church offers a stunning encounter with Florence. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.
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.
Treat yourself to a wonderful meal at Cibrèo Caffè, a top-rated dining spot in Florence. If you're in the mood for something new, try Ristorante Le Volte Firenze, another premier location with a delectable menu. You might also want to book a table at Ristorante Romantico il Paiolo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.
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.
Today, you'll explore some of the most beautiful places in Florence, including a historical landmark, a public square, a church, a monument and much more! Start your day with a visit to Mura Di Lucca. This curiosity-inducing historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Napoleone, which may be one of the most history-steeped places you will experience today.
One of the best things about exploring Florence 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 St Martin Cathedral, a curiosity-inducing church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Guinigi Tower and Piazza Dell'anfiteatro.
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.
Treat yourself to a delightful dinner at Osteria Tripperia Il Magazzino, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante La Spada? It's another excellent option with a diverse menu. Consider reserving a table at Osteria Vecchio Cancello as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.
A leisurely self-drive holiday in Lucca can’t get any better than this! Toast to another amazing day 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.
Savor the day by visiting some of the best places to see in Florence, including a park, a spa, and a church. Start your adventure at Parco Delle Terme. This up-and-coming park is a must-visit for travelers looking for a unique holiday experience. Make your way to Montecatini Terme Centro located in Florence for another exciting encounter.
Next, immerse yourself in the setting of Church Of Saint Mary Of The Assumption. Its respected features will captivate you.
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.
Enjoy a delicious meal at Hotel Lungarno, a highly-rated dining destination in Florence. If you're eager to try something different, consider Residence la Contessina, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Paoli. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.
Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.
Raise your glass to celebrate another day of your laid-back and relaxed road trip experience 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.
Bring your curiosity for today’s adventure around Florence. Some of the town’s most loved attractions await! Leonardo Da Vinci Museum is the perfect place to start. This museum is one of the most locally appreciated places to visit in Florence. Next, head to Padule Di Fucecchio, a frequently visited nature reserve, known for its enchanting features.
Visit these for an interesting touch to your journey.
You’ll be staying at the incredible city of Pisa in this laid-back road trip in Italy. You'll stay here for 1 night.
Exploring new places makes you hungry. Luckily, Pisa has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.
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.
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.
Keep the excitement of the evening going by visiting a bar or two. Bar Mocambo is an excellent place to start. You could also check out Tree, offering a different kind of charm. A last recommendation for the day is Chupiteria. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.
Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Pisa!
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 history-steeped 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.
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.
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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