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.

Today’s route brings fun adventures, photo-friendly spots, and historic treasures. The first attraction of today is Galleria Dell'accademia. This well-known art gallery is a photogenic place to see in Florence. Continue your discovery at Piazza Della Signoria, a history-steeped public square with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Ponte Vecchio. This wondrous historical landmark offers a history-steeped encounter with Florence. Next, make your way to Uffizi Gallery to add another highlight to your day. After that, visit Basilica Of Santa Croce In Florence, a well-known church that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazzale Michelangelo, a top-rated observation deck in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this 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.

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.

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.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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.

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence 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 Pisa and Lucca.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, a public square, a monument, a historical landmark and much more! Begin your adventure at Battistero Di San Giovanni. This is a locally appreciated church you should not miss. Another must-see is Piazza Del Duomo, Pisa, a timeless public square in Florence.

When you’re ready for the next sight, head to Leaning Tower Of Pisa. From there, take a leisurely stroll to Guinigi Tower, another of the city’s locally appreciated attractions. We recommend continuing your self-guided tour at San Michele In Foro, a symbolic place of interest in the city. If time allows, add Mura Di Lucca to your itinerary. This increasingly popular historical landmark offers the perfect finishing touch to your day in Florence.

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar 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!

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Siena Cathedral. This inviting church is a highlight of any visit in the city. Then, enjoy Piazza Del Campo, another UNESCO world heritage-designated attraction that never fails to captivate visitors. Next, head over to Tower Of Mangia, one of the city’s most underrated attractions, known for its respected features.

If you’re looking for more, spend time soaking in the atmosphere of Porta San Giovanni. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Sangimignano1300, an up-and-coming museum, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Duomo before you head back to your hotel.

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 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 lovely dining experience at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!

On day 5 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Castellina in Chianti and San Regolo. You still have 1 night left in Siena.

Today’s agenda in Siena includes a castle and a winery. Rocca Di Castellina In Chianti is must-visit castle and a great starting point for the day. Next, continue your journey to Poggio Amorelli, an intriguing winery, located just a leisurely stroll away. Next, head to Castello Di Brolio, a history-steeped castle, also available for your discovery today.

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

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.

Have a fantastic dining experience at Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink. Similarly, Bar Pinacoteca is well-suited for those looking to unwind in a social setting. San Paolo Pub is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day 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.

Today’s agenda in Siena includes a church, a public square, a castle, a cave system, a monument and much more! Basilica Of San Francesco D'assisi is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Del Comune, an underrated public square, located just a leisurely stroll away. Next, head to Rocca Maggiore, a romantic castle, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the frequently visited Perugia Sotterranea Accesso. If you’re looking for more, The Fontana Maggiore is also a worthwhile attraction that is worthwhile a visit. Lastly, don’t miss Piazza Iv Novembre, a place of symbolic interest in the town.

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.

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 delicious dinner at Ristorante Settimo Sigillo, an excellent option for tonight's dining. Looking for something different? Caffè Baglioni offers a tantalizing alternative with its diverse menu. And don’t miss Bar Pellas. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

Following your dinner, dive into the local bar culture at Tommi Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Valentina, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffe Dal Perugino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to another unforgettable day 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.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. 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. Orvieto Cathedral is the first of them. Spend some time admiring this majestic church before continuing your journey. Orvieto Underground is your next stop. This beloved cave system 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 Pozzo Della Cava. This eye-catching cave is a sight to behold. To round off your sightseeing experience, visit Basilica Of Santa Cristina, Bolsena.

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

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.

Continue the enjoyment post-dinner at Bar Duomo, a cherished local gathering spot renowned for its welcoming atmosphere.

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.

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!

Today’s itinerary in Orvieto covers several incredible sights, including an archeological site, a monument, and a public square. Start your adventure at Colosseum. This globally renowned archeological site is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the UNESCO world heritage-listed wonders of Roman Forum, a must-see archeological site 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 Trevi Fountain. This wondrous monument offers an enriching experience. For a change of pace, head to Pantheon, where you can take in heritage-rich features. Conclude your self-guided sightseeing tour with a visit to Piazza Navona. These sights offer a fulfilling end to a perfect day.

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

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

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

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 3 stops and experience some of the highlights of Montepulciano, San Quirico d'Orcia, and Montalcino. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Orvieto allows for both. Start by heading to Fortezza Medicea. This beloved castle provides an insightful glimpse into the town's identity. Next, discover Cipressi Di San Quirico D'orcia, an eye-catching rock formation, promising a delightful encounter.

Continue your sightseeing with a visit to Fortress Of Montalcino, an intriguing castle.

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.

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.

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.

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