11-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to San Gimignano, Perugia, Orvieto, and Rome
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Escape the ordinary with this exciting 11-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!
This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 4 nights in Florence, 2 nights in San Gimignano, 1 night in Perugia, 1 night in Orvieto, 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 Florence, 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 Florence, Pisa, Lucca, Siena, San Gimignano, Castellina in Chianti, Santa Maria degli Angeli, Perugia, Orvieto, Bolsena, Rome, and Tivoli, 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
- Florence - Arrival day
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- Central Market
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Welcome to Florence, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 3 nights immersing yourself in Florence's charm before embarking on the next leg of your journey.
Florence 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 Central Market, 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.
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.
Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.
Raise a toast to the start of your 11-day road trip in Italy!
Day 2
- Florence
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Drive 7 km, 56 min
- Cathedral of Santa Maria del Fiore
- piazza della Signoria
- Ponte Vecchio
- Uffizi Gallery
- piazzale Michelangelo
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Day 2 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking 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. Cathedral Of Santa Maria Del Fiore is the first of them. Spend some time admiring this romantic church before continuing your journey. Piazza Della Signoria is your next stop. This astonishing 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 Ponte Vecchio. This romantic historical landmark is a sight to behold. To round off your sightseeing experience, visit Uffizi Gallery and Piazzale Michelangelo.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.
Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.
Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 3
- Florence
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Drive 199 km, 3 hours 12 min
- Piazza del Duomo, Pisa
- Pisa Cathedral
- Leaning Tower of Pisa
- Guinigi Tower
- Piazza dell'Anfiteatro
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Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence 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 Pisa and Lucca.
Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming city of Florence. Your adventure starts at Piazza Del Duomo, Pisa, a globally renowned local hot spot. Another notable attraction to explore is Pisa Cathedral. This often recommended church is known for its picture-perfect appeal.
After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This breathtaking monument offers a fascinating experience that many visitors find memorable. Guinigi Tower is also worth visiting, along with Piazza Dell'anfiteatro. These standout landmarks offer unique experiences that add to the day’s enjoyment.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.
Enjoy a lovely dining experience at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.
Extend your evening after a delightful meal by visiting Gosh*, which offers the perfect atmosphere for a night out. Moreover, Antico Caffè Del Moro - Art Bar Firenze is another popular option for a drink or two. Likewise, Quelo Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Savor another day of unforgettable experiences in Italy!
Day 4
- Florence
- San Gimignano
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Drive 118 km, 2 hours 21 min
- Fortezza Medicea
- piazza del Campo
- Siena Cathedral
- Porta San Giovanni
- Piazza del Duomo, San Gimignano
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Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, 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 San Gimignano. You’ll stay here for 2 nights.
Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, breathtaking views, and picturesque spots. Start at Fortezza Medicea (siena), a locally appreciated monument in the city. Then, head to Piazza Del Campo 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 Siena Cathedral. This is one of the city’s most popular enchanting spots of interest. After exploring the church, visit the often recommended Porta San Giovanni. Not far away, you'll also find Piazza Del Duomo. This public square is an inviting highlight 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 61 km, 1 hour 46 min
- Poggio Amorelli
- Tumulo di Montecalvario
- Rocca di Castellina in Chianti
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Wake up to day 5 of your extraordinary road trip in Italy. With 1 night left in San Gimignano, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!
Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the often recommended Poggio Amorelli, a visually striking winery in San Gimignano. Next, go to Tumulo Di Montecalvario.
After visiting Poggio Amorelli and Tumulo Di Montecalvario, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Rocca Di Castellina In Chianti. This respected castle offers a unique experience.
When you’re done exploring for the day, you’ll return to San Gimignano and your accommodation.
As dinnertime approaches, it's time to head out for a bite to eat in San Gimignano. If you are looking to dine at a popular restaurant in the village, it's often a good idea to reserve a table in advance.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 6
- San Gimignano
- Perugia
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Drive 189 km, 3 hours 8 min
- Basilica of San Francesco d'Assisi
- Piazza del Comune
- Basilica di Santa Chiara
- Rocca Paolina
- Piazza IV Novembre
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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 Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Perugia, where you will stay for 1 night.
San Gimignano is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Basilica Of San Francesco D'assisi, a captivating church that is worthwhile a visit in the town. Nearby, you’ll find Piazza Del Comune, enchanting visitors with its visually striking appeal. Continue your exploration at Basilica Di Santa Chiara. This church is one of the town’s most underrated spots.
Enjoy the freedom of exploring San Gimignano at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Rocca Paolina. After exploring the historical landmark, head to the curiosity-inducing Piazza Iv Novembre.
At the end of the day, you will drive to Perugia, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.
As you explore more of Perugia, 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 delightful dinner at Ristorante Settimo Sigillo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Caffè Baglioni? It's another excellent option with a diverse menu. Consider reserving a table at Bar Pellas as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.
Unwind after your meal by stepping into Tommi Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Valentina offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffe Dal Perugino, another top-rated bar in the area.
Raise your glass to another unforgettable day in Italy!
Day 7
- Perugia
- Orvieto
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Drive 123 km, 2 hours 43 min
- Well of St Patrick
- Orvieto Cathedral
- Torre del Moro Orvieto
- Collegiata di Santa Cristina
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Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Orvieto and Bolsena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Orvieto, which will be your home away from home for 1 night.
Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the notable Well Of St. Patrick, a culturally significant monument in Perugia. Next, go to Orvieto Cathedral.
After visiting Well Of St. Patrick and Orvieto Cathedral, have a stroll along Perugia's streets and take in the local charm. Continue your sightseeing by heading to Torre Del Moro Orvieto. This culturally significant monument offers a unique experience. Basilica Of Santa Cristina, Bolsena is another noteworthy attraction worthwhile a visit.
When you’re done exploring for the day, you’ll drive to your hotel in Orvieto. Check in and spend some time relaxing before you head out to tour the town.
After a day of adventure, treat yourself to an exquisite dinner at one of Orvieto's best restaurants.
After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Duomo, a well-loved spot among locals and tourists.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 8
- Orvieto
- Rome
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Drive 124 km, 2 hours 12 min
- Piazza di Spagna
- Trevi Fountain
- Piazza Navona
- Pantheon
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Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 2 nights here for some well-deserved relaxation.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Orvieto allows for both. Start by heading to Piazza Di Spagna. This world-famous public square provides an insightful glimpse into the city's identity. Next, discover Trevi Fountain, a history-steeped monument, promising a delightful encounter.
Continue your sightseeing with a visit to Piazza Navona, a world-famous public square. When you’re done, don’t forget to make a stop at the iconic Pantheon.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
Enjoy a delicious meal at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.
If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.
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
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Drive 8 km, 45 min
- St Peter's Basilica
- Roman Forum
- Colosseum
- Trastevere
- Monti
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Day 9 of your road trip will take you to the best attractions Vatican City has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.
One of the most iconic places you can visit today in Vatican City is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby. You can also explore Monti, a neighborhood that offers a glimpse into local life and culture.
Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at St. Peter's Basilica. Next, dive into the historic features of Roman Forum, a must-visit archeological site in the city.
In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Colosseum, a world-famous archeological site.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.
If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.
As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.
Day 10
- Rome
- Florence
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Drive 314 km, 4 hours 2 min
- Villa d'Este
- Fontana dell'Organo
- Fontana dell'Ovato (o di Tivoli)
- Villa Gregoriana
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On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Tivoli. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Villa D'este is the first of them. Spend some time admiring this enchanting palace before continuing your journey. Fontana Dell'organo is your next stop. This frequently visited monument is one of the best-rated sights in Rome.
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 Fontana Dell'ovato (o Di Tivoli). This romantic monument is a sight to behold. To round off your sightseeing experience, visit Villa Gregoriana.
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.
Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.
Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.
Say good night to Florence and look forward to another great day of your road trip in Italy!
Day 11
- Florence - Departure day
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- Oltrarno
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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 Florence before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.
One of the best things to do on your last day is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.
On your last day in Italy, take time to indulge in shopping at Florence’s popular marketplace, San Lorenzo Market. 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 Florence.
Treat yourself to a delicious dinner at Ristorante Buca Niccolini, an excellent option for tonight's dining. Looking for something different? Essenziale offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante La Grotta Toscana.
You’ll then say farewell to Florence. 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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