11-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to San Gimignano, Perugia, Orvieto, and Rome
Description
Included
Description
Explore the best of Italy on a 11-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Florence, Pisa, Lucca, Siena, San Gimignano, Castellina in Chianti, Santa Maria degli Angeli, Perugia, Orvieto, Bolsena, Rome, and Tivoli. 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 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!
Travel details
Set your travel details to find the best price
Flights
Compare and choose from the best flights to Florence
Car
Choose from the best car rental deals or see all options
Itinerary summary
See a summary of the itinerary that you can fully customize
Personalize your itinerary
Customize tours under each day and destination
Day 1
- Florence - Arrival day
- More
- Central Market
- More
Your road trip adventure in Italy begins as soon as you reach Florence and pick up your car. You’ll stay in Florence for 3 nights and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.
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.
Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.
Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.
Raise a toast to the start of your 11-day road trip in Italy!
Day 2
- Florence
- More
Drive 7 km, 56 min
- Cathedral of Santa Maria del Fiore
- piazza della Signoria
- Ponte Vecchio
- Uffizi Gallery
- piazzale Michelangelo
- More
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.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most spectacular attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This inviting church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Della Signoria and learn what makes this visually striking public square unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the wondrous Ponte Vecchio. After exploring the historical landmark, head to Uffizi Gallery. This extraordinary art gallery is a highlight in Florence. As your day continues, stop by Piazzale Michelangelo, known for its romantic features.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.
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 3
- Florence
- More
Drive 199 km, 3 hours 12 min
- Piazza del Duomo, Pisa
- Pisa Cathedral
- Leaning Tower of Pisa
- Guinigi Tower
- Piazza dell'Anfiteatro
- More
Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!
Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo, Pisa. This UNESCO world heritage-designated public square is a highlight of any visit in the city. Then, enjoy Pisa Cathedral, another historic attraction that never fails to captivate visitors. Next, head over to Leaning Tower Of Pisa, one of the city’s most globally renowned attractions, known for its UNESCO world heritage-designated features.
If you’re looking for more, spend time soaking in the atmosphere of Guinigi Tower. This symbolic monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Dell'anfiteatro, a well-known public square, and take a stroll around the area.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.
Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.
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 4
- Florence
- San Gimignano
- More
Drive 118 km, 2 hours 21 min
- Fortezza Medicea
- piazza del Campo
- Siena Cathedral
- Porta San Giovanni
- Piazza del Duomo, San Gimignano
- More
Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in San Gimignano, which will be your home away from home for 2 nights.
Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This picture-perfect monument is sure to impress. Next on your list is Piazza Del Campo, another must-visit landmark and impressive public square renowned for its romantic 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 visually striking church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Porta San Giovanni, a beloved monument. Nearby, you'll also find Piazza Del Duomo, ready to add charm to your journey.
When you’re done exploring for the day, you’ll drive to your hotel in San Gimignano. Check in and spend some time relaxing before you head out to tour the village.
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.
Celebrate another amazing day of your road trip adventure in Italy!
Day 5
- San Gimignano
- More
Drive 61 km, 1 hour 46 min
- Poggio Amorelli
- Tumulo di Montecalvario
- Rocca di Castellina in Chianti
- More
On day 5 of your road trip, you’ll start and end your day in San Gimignano, but spend part of the day exploring places of interest outside the immediate village. On today's itinerary, you'll find attractions in Castellina in Chianti. You still have 1 night left in San Gimignano.
Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Poggio Amorelli. This up-and-coming winery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Tumulo Di Montecalvario, one of the village’s best highlights.
Next, check out Rocca Di Castellina In Chianti, one of the most intriguing places to see in San Gimignano. This castle is a favorite among locals and travelers alike.
When you’re done exploring for the day, you’ll return to San Gimignano and your accommodation.
As you explore more of San Gimignano, 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.
Say good night to San Gimignano and look forward to another great day of your road trip in Italy!
Day 6
- San Gimignano
- Perugia
- More
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
- More
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.
A blend of fun adventures, scenic views, and photo-friendly spots await you in San Gimignano on today’s itinerary. First up is the popular church, Basilica Of San Francesco D'assisi. Afterward, continue to Piazza Del Comune, a public square every traveler should visit.
As you explore San Gimignano’s charming streets, take in the lively atmosphere and get to know the character of the town. Next, make your way to Basilica Di Santa Chiara. This worthwhile church is an essential stop. Following that, head to Rocca Paolina, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Iv Novembre, an increasingly popular public square in the town.
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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Treat yourself to a wonderful meal at Ristorante Settimo Sigillo, a top-rated dining spot in Perugia. If you're in the mood for something new, try Caffè Baglioni, another premier location with a delectable menu. You might also want to book a table at Bar Pellas. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Perugia.
Following your dinner, dive into the local bar culture at Tommi Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Valentina, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffe Dal Perugino provides excellent drinks and a great atmosphere, ensuring a memorable night out.
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 7
- Perugia
- Orvieto
- More
Drive 123 km, 2 hours 43 min
- Well of St Patrick
- Orvieto Cathedral
- Torre del Moro Orvieto
- Collegiata di Santa Cristina
- More
Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Orvieto and Bolsena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Orvieto. You will spend 1 night here for some well-deserved relaxation.
Bring your curiosity for today’s adventure around Perugia. Some of the village’s most loved attractions await! Well Of St. Patrick is the perfect place to start. This monument is one of the most captivating places to visit in Perugia. Next, head to Orvieto Cathedral, a captivating church, known for its inviting 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 Torre Del Moro Orvieto. This picture-perfect monument is a highly recommended experience. Nearby, you'll also find Basilica Of Santa Cristina, Bolsena. Visit these for an interesting touch to your journey.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Orvieto. Orvieto offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Orvieto. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Round off your dining experience by visiting Bar Duomo, a prime location for a drink.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 8
- Orvieto
- Rome
- More
Drive 124 km, 2 hours 12 min
- Piazza di Spagna
- Trevi Fountain
- Piazza Navona
- Pantheon
- More
On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 2 nights.
Orvieto is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Piazza Di Spagna, a globally renowned public square that is worthwhile a visit in the city. Nearby, you’ll find Trevi Fountain, enchanting visitors with its majestic appeal. Continue your exploration at Piazza Navona. This public square is one of the city’s most iconic spots.
Enjoy the freedom of exploring Orvieto at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pantheon.
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.
Don’t miss out on dining 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.
To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 9
- Rome
- More
Drive 8 km, 45 min
- St Peter's Basilica
- Roman Forum
- Colosseum
- Trastevere
- Monti
- More
On day 9 of your road trip, you will have an entire day to explore Vatican City. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.
Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day. You might also want to visit Monti, a neighborhood offering another perspective on the city.
Start your adventure at St. Peter's Basilica. This timeless major basilica is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the UNESCO world heritage-designated wonders of Roman Forum, a must-see archeological site in the city.
Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Colosseum. This iconic archeological site offers an enriching experience. These sights offer a fulfilling end to a perfect day.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, 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 DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.
Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 10
- Rome
- Florence
- More
Drive 314 km, 4 hours 2 min
- Villa d'Este
- Fontana dell'Organo
- Fontana dell'Ovato (o di Tivoli)
- Villa Gregoriana
- More
Dive into day 10 of your remarkable road trip in Italy. Today you will explore Tivoli, 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 Florence. You’ll stay here for 1 night.
Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Villa D'este. This romantic palace is sure to ignite your curiosity. Next, dive into the UNESCO world heritage-listed features of Fontana Dell'organo, a must-visit monument in the town.
In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Fontana Dell'ovato (o Di Tivoli), a beloved monument. For a change of scene, check out Villa Gregoriana, known for its eye-catching features.
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.
After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.
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.
Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!
Day 11
- Florence - Departure day
- More
- Oltrarno
- More
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.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Florence's best shopping area, San Lorenzo Market. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.
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!
Similar travel packages
Discover other popular vacations in Italy
Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place
Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.