11-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 discover what to see in Florence. You’ll stay in Florence for 2 nights.

Florence is brimming with adventures.

Piazzale Michelangelo is an ideal stop early in the day. This famous 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 photogenic 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 Piazza Della Signoria, a spectacular public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Palazzo Vecchio and Uffizi Gallery. End your day with a visit to Ponte Vecchio, a timeless historical landmark that’s sure to leave a lasting impression.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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.

Head back to your accommodation in Florence and get some rest to prepare for another magical day of your road trip in Italy.

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Pisa and Lucca.

Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Your adventure in Florence is only getting started when you visit Piazza Del Duomo, Pisa, an iconic local hot spot. Another notable attraction to explore is Leaning Tower Of Pisa. This timeless monument is known for its symbolic appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Guinigi Tower. This visually striking monument offers a fascinating experience that many visitors find memorable. San Michele In Foro is also worth visiting, along with Mura Di Lucca. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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 Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Siena. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 3 nights.

Fortezza Medicea (siena) makes a great addition to your morning plans. This up-and-coming monument is a breathtaking place to see in Florence. Continue your discovery at Basilica Of San Domenico, a picture-perfect church 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 Siena Cathedral. This popular church offers an enchanting encounter with Florence. Next, make your way to Piazza Del Campo to add another highlight to your day. After that, visit Pubblico Palace, a frequently visited palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Porta Romana, an intriguing monument 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.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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

Enjoy a delicious meal 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.

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.

Relax 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 still have 2 nights to spend in Siena, there’s no need to rush. Experience San Gimignano and Volterra to the fullest today with this curated day itinerary.

San Gimignano is brimming with adventures.

Whatever your travel style is, Piazza Del Duomo is an essential stop in Siena. This intriguing public square provides an insightful glimpse into the village's identity. Next, discover Palazzo Comunale, Pinacoteca, Torre Grossa, an UNESCO world heritage-listed museum, promising a delightful encounter.

Continue your sightseeing with a visit to Parco Della Rocca, a worthwhile park. When you’re done, don’t forget to make a stop at the increasingly popular Etruscan Museum "mario Guarnacci". Not far away from the museum, you will find the culturally significant Baptistery Of San Giovanni Battista, perfect for a quick visit. Round off your day at Palazzo Incontri Viti, another gem in Siena with respected features to discover.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

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 consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pinacoteca, a bar catering to every mood and preference. San Paolo Pub likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 6 of your road trip, you’ll start and end your day in Siena, where you have 1 night left to stay.

Check out the up-and-coming castle, Rocca Di Castellina In Chianti. Afterward, continue to Poggio Amorelli, a winery 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 Il Molino Di Grace. This frequently visited winery is an essential stop. Following that, head to Castello Di Brolio, another must-visit site that will enhance your experience.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

Make sure to reserve a table at Ristorante San Desiderio, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Le Logge, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Taverna Di Cecco, a hidden gem nestled in Siena. 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 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 places, which are Santa Maria degli Angeli and Perugia. At the end of the day, you will retreat to the hotel of your choice in Perugia, where will spend 1 night.

Awaiting your discovery is the well-known Basilica Of San Francesco D'assisi, a breathtaking church in Siena. Next, go to Rocca Maggiore.

After visiting Basilica Of San Francesco D'assisi and Rocca Maggiore, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Etruscan Arch. This picture-perfect historical landmark offers a unique experience. Perugia Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Iv Novembre, one of the most awe-inspiring places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by The Fontana Maggiore.

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.

Perugia is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Perugia.

Dine in style at Ristorante Settimo Sigillo, a top recommendation for dinner tonight. Or, for a change of pace, Caffè Baglioni boasts a menu that's sure to impress. Also, be sure to check out Bar Pellas. Known as a local hotspot, it’s a great 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.

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

Your itinerary for day 8 of your road trip in Italy includes 1 stop and features some of the highlights of Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 2 nights.

Start your day at Well Of St. Patrick. This standout monument is a captivating place to see in Perugia. Then, wander over to Orvieto Cathedral. If grand sites excite you, this church will be right up your alley. Nearby, you’ll also find Museo Dell'opera Del Duomo. This noteworthy museum is a favorite among visitors.

Perugia offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Orvieto Underground is a beloved spot in the village that will captivate you with its unique charm. When you’re done at the cave system, don’t forget to check out the culturally significant Torre Del Moro Orvieto. Take a moment to appreciate the fascinating details of this increasingly popular monument. Wrap up your self-guided tour of Perugia's top attractions with a visit to Pozzo Della Cava.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Orvieto, it's often a good idea to reserve a table in advance.

After enjoying a fulfilling meal, continue your evening at Bar Duomo, ideal for those looking to unwind with a drink in a comfortable setting.

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

Wake up to day 9 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Rome. With 1 night to stay in Orvieto, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

Colosseum makes a great addition to your morning plans. This timeless archeological site is a historic place to see in Orvieto. Continue your discovery at Roman Forum, a historic 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 globally renowned monument offers an enchanting 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 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, rest up and recharge for the next leg of your road trip in Italy.

Dive into day 10 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Cortona. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Enjoy all that Parterre has to offer. This is a curiosity-inducing park you should not miss. Another must-see is Basilica Of Saint Margaret Of Cortona, an increasingly popular church in Orvieto.

When you’re ready for the next sight, head to Hermitage "le Celle".

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 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.

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