11-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to San Gimignano, Perugia, Orvieto, and Rome

Day 2 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Start by visiting Cathedral Of Santa Maria Del Fiore, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Piazza Della Signoria, another must-visit landmark and extraordinary public square renowned for its visually striking 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 Ponte Vecchio. This respected historical landmark is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Uffizi Gallery, an impressive art gallery. Nearby, you'll also find Piazzale Michelangelo, ready to add charm to your journey.

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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day in Italy!

On day 3 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Discover a day packed with family-friendly attractions, scenic views, and photo-friendly spots in Florence. Begin your sightseeing with Piazza Del Duomo, Pisa. This wondrous public square is one of the top attractions in the city. Proceed to Pisa Cathedral, 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 Leaning Tower Of Pisa. This timeless monument is a traveler-favorite. Not far away, you’ll find Guinigi Tower, another key site on your sightseeing itinerary. Piazza Dell'anfiteatro is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After savoring a delicious meal, step into the vibrant nightlife at Gosh*, where the evening is just getting started. In the same way, Antico Caffè Del Moro - Art Bar Firenze offers a unique charm perfect for experiencing the local bar scene in Florence. Quelo Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Get a good night's sleep and look forward to another great day on the road in Italy!

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.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the frequently visited Fortezza Medicea (siena), a picture-perfect monument in Florence. Next, go to Piazza Del Campo.

After visiting Fortezza Medicea (siena) and Piazza Del Campo, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Siena Cathedral. This majestic church offers a unique experience. Porta San Giovanni is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Del Duomo, one of the most UNESCO world heritage-designated places to visit 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.

After a day of adventure, treat yourself to an exquisite dinner at one of San Gimignano's best restaurants.

Relax and recharge in preparation for another adventurous day in Italy!

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.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Poggio Amorelli. This intriguing winery is an enchanting place to see in San Gimignano. Continue your discovery at Tumulo Di Montecalvario, a photogenic archeological site with stories to tell.

As you stroll around San Gimignano, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Rocca Di Castellina In Chianti. This up-and-coming castle offers a romantic encounter with San Gimignano. 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.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in San Gimignano.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in San Gimignano. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Head back to your accommodation in San Gimignano and get some rest in preparation for another magical day of your road trip in Italy!

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 2 vibrant destinations - Santa Maria degli Angeli and Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of family-friendly attractions, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Basilica Of San Francesco D'assisi. This captivating church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Comune, one of the town’s best highlights.

Next, check out Basilica Di Santa Chiara, one of the most intriguing places to see in San Gimignano. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Rocca Paolina. Wander around and soak in the heritage-rich atmosphere this historical landmark offers. Then, head to Piazza Iv Novembre, a top-rated public square that adds another dimension to your day.

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.

Indulge in a memorable dining experience at one of Perugia's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a delicious meal at Ristorante Settimo Sigillo, a highly-rated dining destination in Perugia. If you're eager to try something different, consider Caffè Baglioni, another top spot with a tantalizing menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Perugia this evening.

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.

Celebrate another amazing day of your road trip adventure in Italy!

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.

Perugia is brimming with adventures. Today’s wonderful stops include a monument and a church. Begin your sightseeing adventure at the captivating Well Of St. Patrick and allow yourself time to explore. Just a short distance away you'll find your next stop, Orvieto Cathedral, a visually striking church that draws visitors from far and near.

Continue your journey to Torre Del Moro Orvieto, one of the village’s most often recommended spots that you shouldn’t miss. Another great site to visit is the locally appreciated Basilica Of Santa Cristina, Bolsena.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Orvieto. If you are looking to dine at a popular restaurant in the town, it's often a good idea to reserve a table in advance.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Duomo, known for its inviting atmosphere.

Raise your glass to another unforgettable day in Italy!

Dive into day 8 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.

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Orvieto. Your adventure starts at Piazza Di Spagna, a wondrous local hot spot. Another notable attraction to explore is Trevi Fountain. This timeless monument is known for its history-steeped appeal.

After soaking in the highlights of these sights, take some time to wander Orvieto's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Navona. This romantic public square offers a fascinating experience that many visitors find memorable. Pantheon is also worth visiting.

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 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.

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.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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 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.

Trastevere is one of the highlights of today. Take your time exploring this iconic neighborhood in Vatican City, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city. Be sure to also visit Monti, a neighborhood that showcases another side of Vatican City.

Just a short distance away you'll find your next stop, Roman Forum, a historic archeological site that draws visitors from far and near.

Continue your journey to Colosseum, one of the city’s most timeless spots that you shouldn’t miss.

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.

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 RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Say good night to Rome and look forward to another great day of your road trip in Italy!

On day 10 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 Tivoli. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Today’s itinerary in Rome covers several incredible sights, including a palace, a monument, and a park. Start your adventure at Villa D'este. This interesting palace is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Fontana Dell'organo, a must-see monument in the town.

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 Fontana Dell'ovato (o Di Tivoli). This beloved monument offers an enriching experience. For a change of pace, head to Villa Gregoriana, where you can take in mesmerizing features. These sights offer a fulfilling end to a perfect day.

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.

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.

Treat yourself to a delicious dinner at Tijuana, an excellent option for tonight's dining. Looking for something different? Djària - American Bar offers a tantalizing alternative with its diverse menu. And don’t miss The Florence Irish Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Savor another day of unforgettable experiences in Italy!