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

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

Start your day at Piazzale Michelangelo. This romantic observation deck is a famous place to see in Florence. Then, wander over to Basilica Of Santa Croce In Florence. If instagrammable sites excite you, this church will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This romantic art gallery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Ponte Vecchio is a wondrous spot in the city that will captivate you with its unique charm. When you’re done at the historical landmark, don’t forget to check out the visually striking Piazza Della Signoria. Take a moment to appreciate the fascinating details of this top-rated public square. Wrap up your self-guided tour of Florence's top attractions with a visit to Galleria Dell'accademia.

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.

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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.

Pisa is brimming with adventures.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 16 min.

Our first attraction recommendation in Pisa is Piazza Del Duomo, Pisa, a globally renowned public square that draws attention for its picture-perfect features. Spend some time soaking in the atmosphere before continuing to Leaning Tower Of Pisa, a historic monument that stands out in the city.

Set your GPS to Lucca and hit the road. Expect a journey of approximately 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Lucca beckons with new experiences!

Savor the day by heading to Guinigi Tower, a curiosity-inducing monument that draws visitors from near and far. When you're done, continue to San Michele In Foro, where you can soak in the historic surroundings.

Next, explore Mura Di Lucca, yet another frequently visited place to see in the area.

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

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

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Gosh*, known for its inviting atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another great option if you’re looking for a place to get the night started. Similarly, Quelo Bar provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

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

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 10 min. When you arrive in Siena, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Fortezza Medicea (siena), a frequently visited monument that everyone visiting Siena should see. Next, head to Tower Of Mangia. This picture-perfect monument is one of the most frequently visited attractions in the region.

If you're keen to see more, don’t miss out on Piazza Del Campo, an awe-inspiring public square popular among locals as well as travelers. Pubblico Palace is an excellent attraction to visit next. Spend some time learning more about this beloved palace before you continue your journey. Lastly, visit Siena Cathedral, a visually striking church and a top attraction in the city.

It’s time to gear up for the next part of your road trip adventure. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Piazza Del Duomo is a worthwhile public square we recommend visiting today. Discover its inviting features before continuing your self-guided tour.

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.

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.

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.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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 1 night to spend in Siena, there’s no need to rush. Experience Castellina in Chianti to the fullest today with this curated day itinerary.

Set your GPS to Castellina in Chianti and hit the road. Expect a journey of approximately 35 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Castellina in Chianti beckons with new experiences!

Poggio Amorelli is a frequently visited winery we recommend visiting today. Discover its enchanting features before continuing your self-guided tour to Tumulo Di Montecalvario, a symbolic archeological site that’s well-regarded in the area.

Next, stop by Rocca Di Castellina In Chianti, a visually striking castle.

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

Siena 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 Siena.

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.

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.

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

Your itinerary for day 6 of your road trip in Italy includes 2 stops and features some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, enjoy the comforts of a top-rated hotel in Perugia, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Santa Maria degli Angeli. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 36 min. Upon reaching Santa Maria degli Angeli, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Basilica Of San Francesco D'assisi is a locally renowned church we recommend visiting today. Discover its historic features before continuing your self-guided tour to Rocca Maggiore, an enchanting castle that’s well-regarded in the area.

After soaking in Santa Maria degli Angeli’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Perugia. Expect your car journey to take a minimum of 34 min. When you arrive in Perugia, it's time to take a break from the road.

Our first attraction recommendation in Perugia is Etruscan Arch, an intriguing historical landmark that draws attention for its respected features. Spend some time soaking in the atmosphere before continuing to Perugia Cathedral, a photogenic church that stands out in the town.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Piazza Iv Novembre, an up-and-coming public square that offers a unique experience. Be sure to also explore The Fontana Maggiore, a nearby monument, highly recommended by other travelers.

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

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 Perugia, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Tommi Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Valentina, a bar that offers unique local touches. Likewise, Caffe Dal Perugino provides an excellent alternative for a fun evening.

Take some time to reflect on your day and savor another beautiful night 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 Orvieto and Sant'Angelo. At the end of the day, you will retreat to the hotel of your choice in Orvieto, where will spend 1 night.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Orvieto. This drive usually takes around 1 hour 17 min, without any stops or traffic disruptions.

Set out on a self-guided sightseeing tour at Well Of St. Patrick and explore the respected features.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Perugia behind. This drive usually takes around 1 hour 17 min. Orvieto welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Orvieto Cathedral, a well-known church that draws visitors from near and far. When you're done, continue to Orvieto Underground, where you can soak in the historic surroundings.

Next, explore Torre Del Moro Orvieto, yet another beloved place to see in the area. After the monument, make time to go to Pozzo Della Cava. This heritage-rich cave is well worth the visit.

Sant'Angelo welcomes you with a multitude of unique vacation experiences.

Spend your afternoon discovering Il Paese Delle Fiabe, a locally appreciated art installation known for its photogenic features.

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.

Orvieto 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 Orvieto.

If you’re not ready to end the night just yet, Bar Duomo offers a perfect venue to relax and savor a drink.

Savor another day of unforgettable experiences in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including San Quirico d'Orcia and Montalcino. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Throughout the day, make sure to take breaks to appreciate the surroundings.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Quirico d'Orcia may take around 1 hour 31 min. Upon your arrival in San Quirico d'Orcia, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Cipressi Di San Quirico D'orcia, a worthwhile rock formation known for its instagrammable features.

Set your GPS to Montalcino and hit the road. Expect a journey of approximately 20 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Montalcino beckons with new experiences!

Spend your afternoon discovering Fortress Of Montalcino, an up-and-coming castle known for its awe-inspiring features. Next, continue your sightseeing at Piazza Del Popolo, an up-and-coming public square.

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!