11-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.

Savor the day by visiting some of the best places to see in Florence, including an observation deck, a church, a public square, a palace, an art gallery, a historical landmark and much more! Start your adventure at Piazzale Michelangelo. This widely recognized observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Of Santa Croce In Florence located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Della Signoria. Its masterful features will captivate you. After the public square, continue your tour of the city with a visit to Palazzo Vecchio. Visitors usually appreciate the history-steeped features of this palace. Next up is Uffizi Gallery, a highly recommended art gallery. For a change of pace, head to Ponte Vecchio. As one of the most globally renowned attractions in Florence, this historical landmark is the perfect place to end your self-guided sightseeing tour.

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 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.

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.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day 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.

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

When you’re ready for the next sight, head to Guinigi Tower. From there, take a leisurely stroll to San Michele In Foro, another of the city’s beloved attractions. We recommend continuing your self-guided tour at Mura Di Lucca, a symbolic place of interest in the city.

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

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.

Enjoy a delicious meal 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.

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

Relax and recharge in preparation for another adventurous day in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 3 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 intriguing monument provides an insightful glimpse into the city's identity. Next, discover Basilica Of San Domenico, a historic church, promising a delightful encounter.

Continue your sightseeing with a visit to Siena Cathedral, a locally renowned church. When you’re done, don’t forget to make a stop at the famous Piazza Del Campo. Not far away from the public square, you will find the awe-inspiring Porta Romana, perfect for a quick visit. Round off your day at Pubblico Palace, another gem in Florence with breathtaking features to discover.

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.

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

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 5 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 2 nights more, there’s no need to rush. Experience San Gimignano and Volterra to the fullest today with this curated day itinerary!

Brace yourself for today’s incredible lineup of attractions in Siena, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Piazza Del Duomo, an increasingly popular public square in the village. Then, head to Palazzo Comunale, Pinacoteca, Torre Grossa and soak in the ambiance of this UNESCO world heritage-listed museum.

There are many interesting places to see in Siena, and when you are ready for more, go to Parco Della Rocca. This is one of the village’s most locally appreciated romantic spots of interest. After exploring the park, visit the often recommended Etruscan Museum "mario Guarnacci". Not far away, you'll also find Palazzo Incontri Viti. This palace is a historic highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Baptistery Of San Giovanni Battista, a worthwhile church in the village.

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 delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Savor another day of unforgettable experiences in Italy!

On day 6 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, Greve in Chianti, and San Regolo. You still have 1 night left in Siena.

Siena is brimming with adventures. Today’s wonderful stops include a castle and a winery. Begin your sightseeing adventure at the frequently visited Rocca Di Castellina In Chianti and allow yourself time to explore. Just a short distance away you'll find your next stop, Poggio Amorelli, a visually striking winery that draws visitors from far and near.

Continue your journey to Il Molino Di Grace, one of the village’s most locally appreciated spots that you shouldn’t miss. Another great site to visit is the locally appreciated Castello Di Brolio.

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.

Don’t miss out on dining at Ristorante San Desiderio, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Le Logge, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

Dive into day 7 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 breathtaking church is sure to impress. Next on your list is Rocca Maggiore, another must-visit landmark and often recommended castle renowned for its visually striking 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 stunning 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 masterful 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 explore more of Perugia, 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 Ristorante Settimo Sigillo, a popular restaurant in Perugia. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Perugia at Caffè Baglioni, 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 Bar Pellas. It’s yet another ideal choice to enhance your time in Perugia tonight.

Round off your dining experience by visiting Tommi Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Valentina, a bar catering to every mood and preference. Caffe Dal Perugino likewise offers a unique atmosphere, perfect for a memorable night out.

Say good night to Perugia and look forward to another great day of your road trip in Italy!

On day 8 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. In the evening, you’ll end up in Orvieto, where you will stay for 2 nights.

Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Perugia. Begin your sightseeing with Well Of St. Patrick. This well-known monument is one of the top attractions in the village. Proceed to Orvieto Cathedral, 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 Museo Dell'opera Del Duomo. This locally appreciated museum is a traveler-favorite. Not far away, you’ll find Orvieto Underground, another key site on your sightseeing itinerary. Torre Del Moro Orvieto is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Pozzo Della Cava and uncover why it's recognized as one of the village's most worthwhile attractions.

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.

After your meal, keep the night alive at a bar like Bar Duomo, known for its lively atmosphere.

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

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

Today’s route brings fun adventures, scenic views, and picturesque spots. The first attraction of today is Colosseum. This timeless archeological site is a historic place to see in Orvieto. Continue your discovery at Roman Forum, a picture-perfect archeological site with stories to tell.

As you stroll around Orvieto, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Trevi Fountain. This wondrous monument offers a history-steeped encounter with Orvieto. Next, make your way to Pantheon to add another highlight to your day. After that, visit Piazza Navona, a wondrous public square that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Orvieto.

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

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

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

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Cortona. 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.

Today’s itinerary in Orvieto covers several incredible sights, including a park, a church, and a monastery. Start your adventure at Parterre. This beloved park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the awe-inspiring wonders of Basilica Of Saint Margaret Of Cortona, a must-see church in the town.

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 Hermitage "le Celle". This often recommended monastery offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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.

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

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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