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

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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Piazzale Michelangelo. This famous observation deck provides an insightful glimpse into the city's identity. Next, discover Basilica Of Santa Croce In Florence, a photogenic church, promising a delightful encounter.

Continue your sightseeing with a visit to Uffizi Gallery, a widely recognized art gallery. When you’re done, don’t forget to make a stop at the globally renowned Ponte Vecchio. Not far away from the historical landmark, you will find the noteworthy Galleria Dell'accademia, perfect for a quick visit. Round off your day at Piazza Della Signoria, another gem in Florence with visually striking features to discover.

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 Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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!

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazza Del Duomo, Pisa is the perfect place to start. This public square is one of the most iconic places to visit in Florence. Next, head to Leaning Tower Of Pisa, a wondrous monument, known for its culturally significant 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 Guinigi Tower. This enchanting monument is a highly recommended experience. Nearby, you'll also find San Michele In Foro and Mura Di Lucca. Visit these for an interesting touch to your journey.

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

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

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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.

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

On day 4 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 Siena and San Gimignano. In the evening, you’ll end up in Siena, where you will stay 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 Fortezza Medicea (siena). This often recommended monument provides an insightful glimpse into the city's identity. Next, discover Tower Of Mangia, a picture-perfect monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Del Campo, an extraordinary public square. When you’re done, don’t forget to make a stop at the up-and-coming Pubblico Palace. Not far away from the palace, you will find the enchanting Piazza Del Duomo, perfect for a quick visit. Round off your day at Siena Cathedral, another gem in Florence with history-steeped 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.

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

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.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Poggio Amorelli. This romantic winery is a highlight of any visit in the village. Then, enjoy Tumulo Di Montecalvario, another respected attraction that never fails to captivate visitors. Next, head over to Rocca Di Castellina In Chianti, one of the village’s most frequently visited attractions, known for its enchanting features.

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

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

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

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

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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 Perugia. You’ll stay here for 1 night.

Start by visiting Basilica Of San Francesco D'assisi, a prime spot to begin your journey. This historic church is sure to impress. Next on your list is Rocca Maggiore, another must-visit landmark and intriguing castle renowned for its romantic 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 Etruscan Arch. This instagrammable historical landmark is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Perugia Cathedral, an often recommended church. Nearby, you'll also find Piazza Iv Novembre, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at The Fontana Maggiore and wrap up your day with its historic appeal.

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.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Perugia tonight.

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

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

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 Sant'Angelo. 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 notable church, known for its history-steeped 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 Orvieto Underground. This historic cave system is a highly recommended experience. Nearby, you'll also find Torre Del Moro Orvieto and Pozzo Della Cava. Visit these for an interesting touch to your journey. Finish the day with a visit to Il Paese Delle Fiabe, a detailed art installation in Perugia.

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 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.

To truly maximize your evening out, consider visiting Bar Duomo after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, 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.

Immerse yourself in Orvieto’s rich culture with today's sightseeing itinerary. Start your journey at Cipressi Di San Quirico D'orcia. This mesmerizing rock formation is sure to ignite your curiosity. Next, dive into the romantic features of Fortress Of Montalcino, a must-visit castle 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 Piazza Del Popolo, an intriguing public square.

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 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 Tijuana, 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 Djària - American Bar, 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 The Florence Irish Pub, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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