9-Day Italy Self-Drive Road Trip With Itinerary from Florence 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.

Today, you'll explore some of the most beautiful places in Florence, including an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Start your day with a visit to Piazzale Michelangelo. This impressive observation deck is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of Santa Croce In Florence, which may be one of the most culturally significant 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 Uffizi Gallery, a widely recognized art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Ponte Vecchio and Piazza Della Signoria. End your day with a visit to Galleria Dell'accademia, a popular art gallery that’s sure to leave a lasting impression.

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.

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.

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.

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Florence is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Piazza Del Duomo, Pisa, a timeless public square that is worthwhile a visit in the city. Nearby, you’ll find Leaning Tower Of Pisa, enchanting visitors with its UNESCO world heritage-listed appeal. Continue your exploration at Guinigi Tower. This monument is one of the city’s most often recommended spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit San Michele In Foro. After exploring the church, head to the intriguing Mura Di Lucca.

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

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.

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.

Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

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.

Prepare for a day full of fun adventures, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea (siena). This up-and-coming monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Tower Of Mangia, one of the city’s best highlights.

Next, check out Piazza Del Campo, one of the most extraordinary places to see in Florence. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pubblico Palace. Wander around and soak in the culturally significant atmosphere this palace offers. Then, head to Siena Cathedral, a top-rated church that adds another dimension to your day. Finally, visit the beloved Piazza Del Duomo, the last of our attraction recommendations for today.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 Siena. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

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

Wake up to day 5 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

A blend of fun adventures, romantic experiences, and scenic views await you in Siena on today’s itinerary. First up is the up-and-coming winery, Poggio Amorelli. Afterward, continue to Tumulo Di Montecalvario, an archeological site every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Rocca Di Castellina In Chianti. This worthwhile castle is an essential stop.

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

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.

Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start. You could also check out Bar Pinacoteca, offering a different kind of charm. A last recommendation for the day is San Paolo Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Head back to your accommodation in Siena 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.

Savor the day by visiting some of the best places to see in Siena, including a church, a castle, a historical landmark, a public square, a monument and much more! Start your adventure at Basilica Of San Francesco D'assisi. This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Rocca Maggiore located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Etruscan Arch. Its culturally significant features will captivate you. After the historical landmark, continue your tour of the town with a visit to Perugia Cathedral. Visitors usually appreciate the photogenic features of this church. Next up is Piazza Iv Novembre, a highly recommended public square. For a change of pace, head to The Fontana Maggiore. As one of the most often recommended attractions in Siena, this monument is the perfect place to end your self-guided sightseeing tour.

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 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.

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.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Orvieto and Sant'Angelo. When you’re not sightseeing, take time to relax at your selected hotel in Orvieto, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and photo-friendly spots. Whether you decide to explore Perugia on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Well Of St. Patrick is the first of them. Spend some time admiring this breathtaking monument before continuing your journey. Orvieto Cathedral is your next stop. This popular church is one of the best-rated sights in Perugia.

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 Orvieto Underground. This visually striking cave system is a sight to behold. To round off your sightseeing experience, visit Torre Del Moro Orvieto and Pozzo Della Cava. If time allows, end your day with Il Paese Delle Fiabe, a photogenic art installation that offers a memorable conclusion to your exploration.

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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Bar Duomo, where the evening is just getting started.

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

Dive into day 8 of your remarkable road trip in Italy. Today you will explore San Quirico d'Orcia and Montalcino, 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 Florence. You’ll stay here for 1 night.

Get ready to discover some of the most iconic wonders in Orvieto, including a rock formation, a castle, and a public square. Start your day at Cipressi Di San Quirico D'orcia. This stunning rock formation is a beloved place to see in Orvieto. Then, wander over to Fortress Of Montalcino. If culturally significant sites excite you, this castle will be right up your alley. Nearby, you’ll also find Piazza Del Popolo. This respected public square is a favorite among visitors.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

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.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.