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 will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Florence.

Florence is brimming with adventures.

Start your day at Cathedral Of Santa Maria Del Fiore. This visually striking church is an extraordinary place to see in Florence. Then, wander over to Piazza Della Signoria. If romantic sites excite you, this public square will be right up your alley. Nearby, you’ll also find Ponte Vecchio. This romantic historical landmark is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Uffizi Gallery is a widely recognized spot in the city that will captivate you with its unique charm. When you’re done at the art gallery, don’t forget to check out the enchanting Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this widely recognized observation deck.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for a true cultural experience.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. Known for great service, it’s a fantastic choice for tonight in Florence.

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.

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

On day 3 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

As you explore Pisa’s charming streets, take in the lively atmosphere and get to know the character of the city.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 16 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

When you're ready for some sights, head to Piazza Del Duomo, Pisa, a globally renowned public square in Pisa. Explore its UNESCO world heritage-designated features at your own pace before you continue your journey to your next attraction, Pisa Cathedral. This frequently visited church is a top recommendation in the area.

When you’re ready to explore more, Leaning Tower Of Pisa is an excellent choice. Spend some time discovering what some claim to be the most picture-perfect monument in the region.

Set your GPS to Lucca and hit the road. Expect a journey of approximately 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Lucca beckons with new experiences!

When you're ready for some sights, head to Guinigi Tower, an often recommended monument in Lucca. Explore its visually striking features at your own pace before you continue your journey to your next attraction, Piazza Dell'anfiteatro. This captivating public square is a top recommendation in the area.

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

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 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.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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

On day 4 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Gimignano are on today's agenda. In the evening, you’ll end up in San Gimignano, where you will stay for 2 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Siena may take around 1 hour 10 min. Upon your arrival in Siena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Fortezza Medicea (siena), an up-and-coming monument that everyone visiting Siena should see. Next, head to Piazza Del Campo. This awe-inspiring public square is one of the most impressive attractions in the region.

If you're keen to see more, don’t miss out on Siena Cathedral, a romantic church popular among locals as well as travelers.

San Gimignano’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 42 min. San Gimignano welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Porta San Giovanni and explore the culturally significant features. Next, make your way to Piazza Del Duomo, another highlight in San Gimignano.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in San Gimignano, it's often a good idea to reserve a table in advance.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 5 of your road trip in Italy, you’ll start and end your day in San Gimignano, but spend the day exploring what’s beyond the village. Since you still have 1 night to spend in San Gimignano, there’s no need to rush. Experience Castellina in Chianti to the fullest today with this curated day itinerary.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Castellina in Chianti. This drive usually takes around 47 min, without any stops or traffic disruptions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Poggio Amorelli, an increasingly popular winery that everyone visiting Castellina in Chianti should see. Next, head to Tumulo Di Montecalvario. This photogenic archeological site is one of the most up-and-coming attractions in the region.

If you're keen to see more, don’t miss out on Rocca Di Castellina In Chianti, a culturally significant castle popular among locals as well as travelers.

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

San Gimignano is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in San Gimignano.

Savor another day of unforgettable experiences in Italy!

Your itinerary for day 6 of your road trip in Italy includes 2 stops and features some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, enjoy the comforts of a top-rated hotel in Perugia, where you'll spend 1 night.

When you’ve had your share of San Gimignano, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Santa Maria degli Angeli. Your travel time is around 2 hours 8 min.

For a more meaningful self-guided tour of the town's best attractions, visit Basilica Of San Francesco D'assisi, a popular church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Piazza Del Comune and admire its grand features.

When you’re ready, continue to Basilica Di Santa Chiara, an increasingly popular church beloved by locals and tourists alike.

Continue your road trip and head to your next destination, Perugia. This car ride takes around 29 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Rocca Paolina, a frequently visited historical landmark that everyone visiting Perugia should see. Next, head to Piazza Iv Novembre. This enchanting public square is one of the most frequently visited attractions in the region.

When you’re done exploring for the day, you’ll drive to your hotel in Perugia. Check in and relax before you head out to tour the city.

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

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Tommi Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Valentina offers an ideal atmosphere to enjoy the pleasures of the night. Caffe Dal Perugino is also a great option that provides a perfect setting for a relaxing evening.

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

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Orvieto and Bolsena. At the end of the day, you’ll unwind at one of the finest accommodations in Orvieto, where you'll spend 1 night.

After soaking in Perugia’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Orvieto. Expect your car journey to take a minimum of 1 hour 17 min. When you arrive in Orvieto, it's time to take a break from the road.

When you're ready for some sights, head to Well Of St. Patrick, a popular monument in Orvieto. Explore its picture-perfect features at your own pace before you continue your journey.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Orvieto may take around 1 hour 17 min. Upon your arrival in Orvieto, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready for some sights, head to Orvieto Cathedral, a popular church in Orvieto. Explore its enchanting features at your own pace before you continue your journey to your next attraction, Torre Del Moro Orvieto. This curiosity-inducing monument is a top recommendation in the area.

When you arrive in Bolsena, it's time to take a break from the road.

When you're ready for some sights, head to Basilica Of Santa Cristina, Bolsena, a beloved church in Bolsena. Explore its picture-perfect features at your own pace before you continue your journey.

At the end of the day, you will drive to Orvieto, 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 Orvieto. Enjoy a relaxing evening as you savor delicious local cuisine.

Unwind after your meal by stepping into Bar Duomo. This venue is celebrated for its extensive drink selections and cozy vibes.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Rome, where you’ll be staying for 2 nights.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 1 hour 33 min, without any stops or traffic disruptions.

Set out on a self-guided sightseeing tour at Piazza Di Spagna and explore the visually striking features. Next, make your way to Trevi Fountain, another highlight in Rome. When you’re done exploring the monument, continue to Piazza Navona, a visually striking public square.

Nearby, you will also find Pantheon. This iconic monument is a top place to see in the area.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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.

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

Take some time to reflect on your day and savor another beautiful night in Italy.

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Tivoli. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 1 night.

Fasten your seatbelt and make your way to your next stop — Tivoli, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Tivoli may take around 49 min without traffic disruptions. Upon arrival in Tivoli, we highly recommend checking out some of the top attractions.

Villa D'este is an interesting palace we recommend visiting today. Discover its respected features before continuing your self-guided tour to Fontana Dell'organo, a history-steeped monument that’s well-regarded in the area.

Next, stop by Fontana Dell'ovato (o Di Tivoli), an UNESCO world heritage-listed monument. While you’re nearby, don’t forget to visit Villa Gregoriana, an idyllic and truly unique park.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

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

Savor the flavors at Tijuana, a top pick for dinner tonight. Alternatively, Djària - American Bar beckons with its unique menu offerings. Also, consider The Florence Irish Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.