10-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to Siena, Perugia, and Orvieto

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 Florence by discovering the best things there are to see and do in the city.

A blend of family-friendly attractions, photo-friendly spots, and history-rich sites await you in Florence on today’s itinerary. First up is the locally renowned art gallery, Galleria Dell'accademia. Afterward, continue to Piazza Della Signoria, a public square every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Ponte Vecchio. This timeless historical landmark is an essential stop. Following that, head to Uffizi Gallery, another must-visit site that will enhance your experience. Don’t forget to stop by Basilica Of Santa Croce In Florence, a well-known church in the city. Finally, end your day with a visit to Piazzale Michelangelo, a history-steeped observation deck that offers the perfect conclusion to your sightseeing of the 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

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 well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly spots. 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. Battistero Di San Giovanni is the first of them. Spend some time admiring this UNESCO world heritage-designated church before continuing your journey. Piazza Del Duomo, Pisa is your next stop. This timeless 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 Leaning Tower Of Pisa. This breathtaking monument is a sight to behold. To round off your sightseeing experience, visit Guinigi Tower and San Michele In Foro. If time allows, end your day with Mura Di Lucca, a romantic historical landmark that offers a memorable conclusion to your exploration.

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

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.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Gosh*, a well-loved spot among locals and tourists. Or, head to Antico Caffè Del Moro - Art Bar Firenze. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Quelo Bar, another top-rated place in the area.

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

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 Siena. You’ll stay here for 2 nights.

Today, you'll explore some of the most beautiful places in Florence, including a church, a public square, a monument, a museum and much more! Start your day with a visit to Siena Cathedral. This well-known church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Campo, which may be one of the most romantic places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Tower Of Mangia, an increasingly popular monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Porta San Giovanni and Sangimignano1300. End your day with a visit to Piazza Del Duomo, a worthwhile public square that’s sure to leave a lasting impression.

At the end of the day, you will drive to Siena, 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 Siena's best restaurants.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena 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 Castellina in Chianti and San Regolo.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most intriguing attractions included on the itinerary is Rocca Di Castellina In Chianti. This enchanting castle will help you start your sightseeing on top. Then, take a leisurely stroll to Poggio Amorelli and learn what makes this romantic winery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the curiosity-inducing Castello Di Brolio.

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

As you explore more of Siena, 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.

Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pinacoteca, a bar catering to every mood and preference. San Paolo Pub likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 1 night.

Get ready to discover some of the most iconic wonders in Siena, including a church, a public square, a castle, a cave system, a monument and much more! Start your day at Basilica Of San Francesco D'assisi. This breathtaking church is a well-known place to see in Siena. Then, wander over to Piazza Del Comune. If history-steeped sites excite you, this public square will be right up your alley. Nearby, you’ll also find Rocca Maggiore. This grand castle is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Perugia Sotterranea Accesso is a curiosity-inducing spot in the town that will captivate you with its unique charm. When you’re done at the cave system, don’t forget to check out the culturally significant The Fontana Maggiore. Take a moment to appreciate the fascinating details of this curiosity-inducing monument in Siena.

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

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.

Make sure to reserve a table at Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Tommi Bar, a top-rated bar in the area. For other recommendations, Valentina provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffe Dal Perugino offers a memorable night with diverse drink options and excellent service.

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

On day 7 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 and Bolsena. In the evening, you’ll end up in Orvieto, where you will stay for 2 nights.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the locally renowned Orvieto Cathedral, a visually striking church in Perugia. Next, go to Orvieto Underground.

After visiting Orvieto Cathedral and Orvieto Underground, take time to explore Perugia's streets and absorb its charm. Continue your sightseeing by heading to Pozzo Della Cava. This standout cave offers a unique experience. Basilica Of Santa Cristina, Bolsena is another noteworthy stop.

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.

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 and reflect on the day's adventures.

Round off your dining experience by visiting Bar Duomo, a prime location for a drink.

Savor another day of unforgettable experiences in Italy!

On day 8 of your road trip in Italy, you’ll start and end your day in Orvieto, but spend the day exploring what’s beyond the town. Since you will return to Orvieto for 1 night more, there’s no need to rush. Experience Rome to the fullest today with this curated day itinerary!

Start by visiting Colosseum, a prime spot to begin your journey. This culturally significant archeological site is sure to impress. Next on your list is Roman Forum, another must-visit landmark and timeless archeological site renowned for its historic features.

While exploring and sightseeing, take time to savor the ambiance of Orvieto by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Trevi Fountain. This romantic monument is a remarkable attraction that offers a unique experience. Pantheon also adds charm to your journey, and Piazza Navona wraps up your day with its romantic appeal.

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

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

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Montepulciano, San Quirico d'Orcia, and Montalcino. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Get ready for an exciting day in Orvieto. Today’s sightseeing agenda includes a castle and a rock formation. Begin your adventure at Fortezza Medicea. This is an often recommended castle you should not miss. Another must-see is Cipressi Di San Quirico D'orcia, an up-and-coming rock formation in Orvieto.

When you’re ready for the next sight, head to Fortress Of Montalcino.

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.

Treat yourself to a wonderful meal at Tijuana, a top-rated dining spot in Florence. If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu. You might also want to book a table at The Florence Irish Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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