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 a popular art gallery you should not miss. Another must-see is Piazza Della Signoria, an extraordinary 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 top-rated attractions. We recommend continuing your self-guided tour at Basilica Of Santa Croce In Florence, an inviting place of interest in the city. If time allows, add Piazzale Michelangelo to your itinerary. This astonishing 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 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.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery 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!

On day 3 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a monument, a historical landmark and much more! Start your adventure at Battistero Di San Giovanni. This often recommended church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Piazza Del Duomo, Pisa, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Leaning Tower Of Pisa. This globally renowned monument offers an enriching experience. For a change of pace, head to Guinigi Tower, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to San Michele In Foro and Mura Di Lucca. These sights offer a fulfilling end to a perfect day.

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

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Savor the day by visiting some of the best places to see in Florence, including a church, a public square, a monument, a museum and much more! Start your adventure at Siena Cathedral. This locally renowned church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Campo located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Tower Of Mangia. Its breathtaking features will captivate you. After the monument, continue your tour of the city with a visit to Porta San Giovanni. Visitors usually appreciate the breathtaking features of this monument. Next up is Sangimignano1300, a highly recommended museum. For a change of pace, head to Piazza Del Duomo. As one of the most beloved attractions in Florence, this public square is the perfect place to end your self-guided sightseeing tour.

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.

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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

If you’re not ready to end the night just yet, Meet Life Cafè offers a perfect venue to relax and savor a drink. Similarly, Maudit Pub is well-suited for those looking to unwind in a social setting. Bar Impero Siena is another excellent spot to enjoy a nightcap after a delightful meal.

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.

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

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Rocca Di Castellina In Chianti. This often recommended castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Poggio Amorelli, one of the village’s best highlights.

Next, check out Castello Di Brolio, one of the most often recommended places to see in Siena. This castle is a favorite among locals and travelers alike.

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

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

Enjoy a lovely dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time 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.

Relax and recharge in preparation for another adventurous day 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.

A blend of fun adventures, breathtaking views, and picturesque spots await you in Siena on today’s itinerary. First up is the interesting church, Basilica Of San Francesco D'assisi. Afterward, continue to Piazza Del Comune, a public square every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the town. Next, make your way to Rocca Maggiore. This worthwhile castle is an essential stop. Following that, head to Perugia Sotterranea Accesso, another must-visit site that will enhance your experience. Don’t forget to stop by The Fontana Maggiore, a beloved monument in the town. Finally, end your day with a visit to Piazza Iv Novembre, a visually striking public square that offers the perfect conclusion to your sightseeing of the day.

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.

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

Treat yourself to a delightful dinner at Ristorante Settimo Sigillo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Caffè Baglioni? It's another excellent option with a diverse menu. Consider reserving a table at Bar Pellas as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

Keep the excitement of the evening going by visiting a bar or two. Tommi Bar is an excellent place to start. You could also check out Valentina, offering a different kind of charm. A last recommendation for the day is Caffe Dal Perugino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Brace yourself for today’s incredible lineup of attractions in Perugia, featuring fun adventures, romantic experiences, and scenic views. Start at Orvieto Cathedral, an interesting church in the town. Then, head to Orvieto Underground and soak in the ambiance of this instagrammable cave system.

There are many interesting places to see in Perugia, and when you are ready for more, go to Pozzo Della Cava. This is one of the town’s most increasingly popular history-steeped spots of interest. After exploring the cave, visit the up-and-coming Basilica Of Santa Cristina, Bolsena.

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.

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

Keep the evening going at Bar Duomo, a great choice for enjoying the after-dinner hours with a drink.

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

On day 8 of your road trip, you’ll start and end your day in Orvieto, but spend part of the day exploring places of interest outside the immediate town. On today's itinerary, you'll find attractions in Rome. You still have 1 night left in Orvieto.

Today's adventure in Orvieto promises more breathtaking discoveries and enriching experiences! Begin at Colosseum. This UNESCO world heritage-listed archeological site is a highlight of any visit in the city. Then, enjoy Roman Forum, another historic attraction that never fails to captivate visitors. Next, head over to Trevi Fountain, one of the city’s most iconic attractions, known for its grand features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This photogenic monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Navona, an iconic public square, and take a stroll around the area.

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

As you explore more of Orvieto, 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.

Savor another day of unforgettable experiences in Italy!

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Montepulciano, 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.

Today's adventure in Orvieto promises more breathtaking discoveries and enriching experiences! Begin at Fortezza Medicea. This visually striking castle is a highlight of any visit in the town. Then, enjoy Cipressi Di San Quirico D'orcia, another romantic attraction that never fails to captivate visitors. Next, head over to Fortress Of Montalcino, one of the town’s most beloved attractions, known for its romantic features.

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.

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.

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.

Savor another day of unforgettable experiences in Italy!