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

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes an art gallery, a public square, a historical landmark, a church, an observation deck and much more! Begin your adventure at Galleria Dell'accademia. This is an interesting art gallery you should not miss. Another must-see is Piazza Della Signoria, a top-rated public square in Florence.

When you’re ready for the next sight, head to Ponte Vecchio. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s widely recognized attractions. We recommend continuing your self-guided tour at Basilica Of Santa Croce In Florence, a standout place of interest in the city. If time allows, add Piazzale Michelangelo to your itinerary. This spectacular observation deck offers the perfect finishing touch to your day in Florence.

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

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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

On day 3 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 1 night more, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary!

Today’s well-planned self-sightseeing route offers several fun adventures, breathtaking views, and picturesque 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 breathtaking church before continuing your journey. Piazza Del Duomo, Pisa is your next stop. This world-famous 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 visually striking 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.

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.

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly 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.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Say good night to Florence and look forward to another great 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Siena Cathedral. This interesting church provides an insightful glimpse into the city's identity. Next, discover Piazza Del Campo, a visually striking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Tower Of Mangia, an up-and-coming monument. When you’re done, don’t forget to make a stop at the curiosity-inducing Porta San Giovanni. Not far away from the monument, you will find the visually striking Piazza Del Duomo, perfect for a quick visit. Round off your day at Sangimignano1300, another gem in Florence with photogenic features to discover.

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

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

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 5 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Start by visiting Rocca Di Castellina In Chianti, a prime spot to begin your journey. This history-steeped castle is sure to impress. Next on your list is Poggio Amorelli, another must-visit landmark and intriguing winery renowned for its awe-inspiring features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Castello Di Brolio. This romantic castle is an essential place to visit for anyone looking for the full Siena experience.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Let the evening flow smoothly from dinner to drinks at Charlie Mixology Bar Di Aldinucci Riccardo, a top-rated bar in the area. For other recommendations, Bar Pinacoteca provides a perfect setting for rounding out your night with style and great drinks. Likewise, San Paolo Pub offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences in Italy!

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your selected hotel in Perugia, where you’ll be staying for 1 night.

Bring your curiosity for today’s adventure around Siena. Some of the town’s most loved attractions await! Basilica Of San Francesco D'assisi is the perfect place to start. This church is one of the most well-known places to visit in Siena. Next, head to Piazza Del Comune, an often recommended public square, known for its visually striking 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 Rocca Maggiore. This culturally significant castle is a highly recommended experience. Nearby, you'll also find Perugia Sotterranea Accesso and The Fontana Maggiore. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Iv Novembre, a history-steeped public square in Siena.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Perugia. Perugia 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 Perugia's best restaurants.

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

After savoring a delicious meal, step into the vibrant nightlife at Tommi Bar, where the evening is just getting started. In the same way, Valentina offers a unique charm perfect for experiencing the local bar scene in Perugia. Caffe Dal Perugino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Head back to your accommodation in Perugia and get some rest in preparation for another magical day of your road trip 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 2 nights.

Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Perugia. Begin your sightseeing with Orvieto Cathedral. This popular church is one of the top attractions in the town. Proceed to Orvieto Underground, another must-visit attraction.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Pozzo Della Cava. This worthwhile cave is a traveler-favorite. Not far away, you’ll find Basilica Of Santa Cristina, Bolsena, another key site on your sightseeing itinerary.

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 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 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.

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

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Orvieto for your remaining 1 night in the town 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 Rome.

Today, you'll explore some of the most beautiful places in Orvieto, including an archeological site, a monument, and a public square. Start your day with a visit to Colosseum. This wondrous archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Roman Forum, which may be one of the most picture-perfect places you will experience today.

One of the best things about exploring Orvieto 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 Trevi Fountain, an iconic monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pantheon and Piazza Navona.

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

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.

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

On day 9 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 Montepulciano, San Quirico d'Orcia, and Montalcino. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea. This often recommended castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Cipressi Di San Quirico D'orcia, one of the town’s best highlights.

Next, check out Fortress Of Montalcino, one of the most frequently visited places to see in Orvieto. This castle is a favorite among locals and travelers alike.

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

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.

Dine in style at Tijuana, a top recommendation for dinner tonight. Or, for a change of pace, Djària - American Bar boasts a menu that's sure to impress. Also, be sure to check out The Florence Irish Pub. Known as a local hotspot, it’s a great choice for tonight in Florence.

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