10-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, San Gimignano, Santa Maria degli Angeli, and Rome
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Explore the best of Italy on a 10-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Pisa, Florence, Siena, San Gimignano, Greve in Chianti, Montefioralle, Santa Maria degli Angeli, Rome, and Orvieto. 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 San Gimignano, 1 night in Santa Maria degli Angeli, and 2 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, Siena, San Gimignano, Greve in Chianti, Montefioralle, Santa Maria degli Angeli, 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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- 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.
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.
Enjoy a lovely dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at il Mercante, 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 La Ghiotteria. It’s yet another ideal choice to enhance your time in Pisa tonight.
Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Raise a toast to the start of your 10-day road trip in Italy!
Day 2
- Pisa
- Florence
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Drive 88 km, 1 hour 39 min
- Leaning Tower of Pisa
- Piazza del Duomo, Pisa
- Ponte Vecchio
- Uffizi Gallery
- piazza della Signoria
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Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.
Pisa is home to plenty of attractions that offer fun adventures, scenic views, and photo-friendly spots! Start at Leaning Tower Of Pisa, a world-famous monument that is worthwhile a visit in the city. Nearby, you’ll find Piazza Del Duomo, Pisa, enchanting visitors with its stunning appeal. Continue your exploration at Ponte Vecchio. This historical landmark is one of the city’s most timeless spots.
Enjoy the freedom of exploring Pisa at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Uffizi Gallery. After exploring the art gallery, head to the top-rated Piazza Della Signoria.
When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.
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.
Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 3
- Florence
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Drive 9 km, 1 hour 19 min
- David
- Galleria dell'Accademia
- Central Market
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Croce in Florence
- piazzale Michelangelo
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Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, picturesque spots, and history-rich sites. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. David is the first of them. Galleria Dell'accademia is your next stop. This popular art gallery 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 Central Market. This picture-perfect food market is a sight to behold. To round off your sightseeing experience, visit Cathedral Of Santa Maria Del Fiore and Basilica Of Santa Croce In Florence. If time allows, end your day with Piazzale Michelangelo, a history-steeped observation deck that offers a memorable conclusion to your exploration.
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.
After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.
Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, 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 excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.
Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!
Day 4
- Florence
- San Gimignano
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Drive 117 km, 2 hours 16 min
- Palazzo Salimbeni
- piazza del Campo
- Siena Cathedral
- Porta San Giovanni
- Parco della Rocca
- Piazza del Duomo, San Gimignano
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On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in San Gimignano, where you’ll be staying for 2 nights.
Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Palazzo Salimbeni is the perfect place to start. This palace is one of the most often recommended places to visit in Florence. Next, head to Piazza Del Campo, a top-rated public square, known for its romantic 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 Siena Cathedral. This history-steeped church is a highly recommended experience. Nearby, you'll also find Porta San Giovanni and Parco Della Rocca. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Duomo, an UNESCO world heritage-designated public square in Florence.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in San Gimignano. San Gimignano 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 San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Get a good night's sleep and look forward to another great day on the road in Italy!
Day 5
- San Gimignano
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Drive 97 km, 2 hours 12 min
- Castle of Verrazzano
- Fattoria Viticcio
- Villa Calcinaia - Conti Capponi
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On day 5 of your road trip, you’ll start and end your day in San Gimignano, where you'll stay for 1 night more.
Today's adventure in San Gimignano promises more breathtaking discoveries and enriching experiences! Begin at Castle Of Verrazzano. This history-steeped castle is a highlight of any visit in the town. Then, enjoy Fattoria Viticcio, another idyllic attraction that never fails to captivate visitors. Next, head over to Villa Calcinaia - Conti Capponi, one of the town’s most often recommended attractions, known for its visually striking features.
When you’re done exploring for the day, you’ll return to San Gimignano and your accommodation.
Indulge in a memorable dining experience at one of San Gimignano's most popular restaurants, and connect with friendly locals for an authentic adventure.
Head back to your accommodation in San Gimignano and get some rest in preparation for another magical day of your road trip in Italy!
Day 6
- San Gimignano
- Assisi
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Drive 169 km, 3 hours 29 min
- Basilica of San Francesco d'Assisi
- Porta San Giacomo
- Portico of Monte Frumentario
- Rocca Maggiore
- Basilica di Santa Chiara
- Piazza del Comune
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Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Santa Maria degli Angeli. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Santa Maria degli Angeli. You will spend 1 night here for some well-deserved relaxation.
Today’s route brings fun adventures, scenic views, and photo-friendly spots. The first attraction of today is Basilica Of San Francesco D'assisi. This locally renowned church is a historic place to see in San Gimignano.
As you stroll around San Gimignano, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Portico Of Monte Frumentario. This increasingly popular historical landmark offers a culturally significant encounter with San Gimignano. Next, make your way to Rocca Maggiore to add another highlight to your day. After that, visit Basilica Di Santa Chiara, a worthwhile church that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Del Comune, an intriguing public square in the town. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in San Gimignano.
At the end of the day, you will drive to Santa Maria degli Angeli, 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 Santa Maria degli Angeli's best restaurants.
Unwind after your meal by stepping into Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings. This venue is celebrated for its extensive drink selections and cozy vibes.
Raise your glass to another unforgettable day in Italy!
Day 7
- Assisi
- Rome
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Drive 185 km, 3 hours 29 min
- Colosseum
- Roman Forum
- Pantheon
- Trevi Fountain
- Spanish Steps
- Piazza di Spagna
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Dive into day 7 of your remarkable road trip in Italy. Today you will explore Rome, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Rome. You’ll stay here for 2 nights.
Brace yourself for today’s incredible lineup of attractions in Santa Maria degli Angeli, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Colosseum, a timeless archeological site in the city. Then, head to Roman Forum and soak in the ambiance of this breathtaking archeological site.
There are many interesting places to see in Santa Maria degli Angeli, and when you are ready for more, go to Pantheon. This is one of the city’s most timeless culturally significant spots of interest. After exploring the monument, visit the world-famous Trevi Fountain. Not far away, you'll also find Spanish Steps. This public square is a culturally significant highlight in Santa Maria degli Angeli. Before wrapping up your self-guided sightseeing tour, head to Piazza Di Spagna, a timeless public square in the city.
When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and spend some time relaxing before you head out to tour the city.
Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.
Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. 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 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.
Relax and recharge in preparation for another adventurous day in Italy!
Day 8
- Rome
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Drive 11 km, 1 hour 25 min
- Vatican Museums
- St Peter's Basilica
- Sistine Chapel
- piazza del Popolo
- Piazza Navona
- Via del Corso
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On day 8 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.
Via del Corso is one of the highlights of today. Take your time exploring this iconic street in Vatican City, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.
Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Next, go to St. Peter's Basilica.
Piazza Del Popolo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Navona, one of the most enchanting places to visit in Rome.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.
As you explore more of Rome, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.
Treat yourself to a wonderful meal at RomAntica, a top-rated dining spot in Rome. If you're in the mood for something new, try Coso Ristorante, another premier location with a delectable menu. You might also want to book a table at DEROMA - Farine Romane. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.
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.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 9
- Rome
- Pisa
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Drive 370 km, 4 hours 48 min
- Well of St Patrick
- Orvieto Cathedral
- Museo dell'Opera del Duomo
- Orvieto subterranea
- Torre del Moro Orvieto
- Pozzo della Cava
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On day 9 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.
Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Rome. Begin your sightseeing with Well Of St. Patrick. This popular monument is one of the top attractions in the village. Proceed to Orvieto Cathedral, another must-visit attraction.
As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Museo Dell'opera Del Duomo. This curiosity-inducing museum is a traveler-favorite. Not far away, you’ll find Orvieto Underground, another key site on your sightseeing itinerary. Torre Del Moro Orvieto is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Pozzo Della Cava and uncover why it's recognized as one of the village's most intriguing attractions.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Pisa. Pisa offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
As dinnertime approaches, it's time to head out for a bite to eat in Pisa. 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 Ristorante Capodimonte Pisa, a highly-rated dining destination in Pisa. If you're eager to try something different, consider La Locanda Dei Pisani Doc Pisa, another top spot with a tantalizing menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Pisa this evening.
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.
Head back to your accommodation in Pisa and get some rest in preparation for another magical day of your road trip in Italy!
Day 10
- Pisa - Departure day
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- Palazzo Blu
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Day 10 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 Blu, a historic art gallery before you head out.
Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Pisa.
Enjoy a lovely meal at Restaurant -Pizzeria Il Mio Capriccio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante alle Bandierine is another top choice with a popular menu.
You’ll then say farewell to Pisa. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!
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