10-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to Siena, Perugia, and Orvieto

Day 2 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Look forward to a unique sightseeing adventure at the interesting Galleria Dell'accademia and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Della Signoria, an enchanting public square that draws visitors from far and near.

Continue your journey to Ponte Vecchio, one of the city’s most world-famous spots that you shouldn’t miss. Another great site to visit is the extraordinary Uffizi Gallery. When you're finished at the art gallery, Basilica Of Santa Croce In Florence awaits your visit. This church is a culturally significant highlight on today's itinerary. Last up is an observation deck - the extraordinary Piazzale Michelangelo.

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.

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

Don’t miss out on dining 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.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Raise your glass and celebrate another amazing 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.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 14 min. Pisa welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Battistero Di San Giovanni and explore the picture-perfect features. Next, make your way to Piazza Del Duomo, Pisa, another highlight in Pisa. When you’re done exploring the public square, continue to Leaning Tower Of Pisa, a picture-perfect monument.

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!

For a more meaningful self-guided tour of the city's best attractions, visit Guinigi Tower, an intriguing monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to San Michele In Foro and admire its picture-perfect features.

When you’re ready, continue to Mura Di Lucca, a worthwhile historical landmark beloved by locals and tourists alike.

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

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for a true cultural experience.

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.

Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass and celebrate another amazing day of your road trip 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 places, which are Siena and San Gimignano. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 2 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Siena. This drive usually takes around 1 hour 12 min, without any stops or traffic disruptions.

Set out on a self-guided sightseeing tour at Siena Cathedral and explore the grand features. Next, make your way to Piazza Del Campo, another highlight in Siena. When you’re done exploring the public square, continue to Tower Of Mangia, a picture-perfect monument.

Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Set out on a self-guided sightseeing tour at Porta San Giovanni and explore the UNESCO world heritage-designated features. Next, make your way to Sangimignano1300, another highlight in San Gimignano. When you’re done exploring the museum, continue to Piazza Del Duomo, a visually striking public square.

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

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

Don’t miss out on dining 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.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day 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 and San Regolo to the fullest today with this curated day itinerary.

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Castellina in Chianti. This drive usually takes around 31 min, without any stops or traffic disruptions.

Savor the day by heading to Rocca Di Castellina In Chianti, a curiosity-inducing castle that draws visitors from near and far. When you're done, continue to Poggio Amorelli, where you can soak in the visually striking surroundings.

When you’re ready to jump back into the car and say goodbye to Castellina in Chianti, you’ll hit the road in the direction of San Regolo. This drive usually takes around 38 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castello Di Brolio, a frequently visited castle that everyone visiting San Regolo should see.

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

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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Let the evening flow smoothly from dinner to drinks at Charlie Mixology Bar Di Aldinucci Riccardo, a top-rated bar in the area. For other recommendations, Bar Pinacoteca provides a perfect setting for rounding out your night with style and great drinks. Likewise, San Paolo Pub offers a memorable night with diverse drink options and excellent service.

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

Continue your road trip and head to your next destination, Santa Maria degli Angeli. This car ride takes around 1 hour 36 min.

Basilica Of San Francesco D'assisi is an interesting church we recommend visiting today. Discover its UNESCO world heritage-listed features before continuing your self-guided tour to Piazza Del Comune, a history-steeped public square that’s well-regarded in the area.

Next, stop by Rocca Maggiore, an enchanting castle.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Perugia. This drive usually takes around 32 min, without any stops or traffic disruptions.

One of our top recommendations for your sightseeing is Perugia Sotterranea Accesso. Spend some time admiring the instagrammable features of the cave system before you continue to your next stop. Then, head to The Fontana Maggiore. This increasingly popular monument is a traveler-favorite in the town.

If you're keen to see more, continue to Piazza Iv Novembre. Feed your curiosity by learning something new about the public square.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Perugia. Perugia 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. If you are looking to dine at a popular restaurant in Perugia, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Perugia tonight.

After enjoying a fulfilling meal, continue your evening at Tommi Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Valentina offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffe Dal Perugino provides an excellent environment for a relaxed and enjoyable evening.

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

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Orvieto and Bolsena. At the end of the day, you’ll unwind at one of the finest accommodations in Orvieto, where you'll spend 2 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Orvieto may take around 1 hour 19 min. Upon your arrival in Orvieto, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready for some sights, head to Orvieto Cathedral, an interesting church in Orvieto. Explore its majestic features at your own pace before you continue your journey to your next attraction, Orvieto Underground. This curiosity-inducing cave system is a top recommendation in the area.

When you’re ready to explore more, Pozzo Della Cava is an excellent choice. Spend some time discovering what some claim to be the most history-steeped cave in the region.

When you arrive in Bolsena, 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 Basilica Of Santa Cristina, Bolsena, an intriguing church that everyone visiting Bolsena should see.

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.

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.

Continue your lively evening at Bar Duomo, a perfect place for winding down or revving up the night, depending on which mood you’re in.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 8 of your road trip, you’ll start and end your day in Orvieto, where you have 1 night left to stay.

Fasten your seatbelt and make your way to your next stop — Rome, home to many well-known sights in the region. Keep in mind that your travel time from Orvieto to Rome may take around 1 hour 37 min without traffic disruptions. Upon arrival in Rome, we highly recommend checking out some of the top attractions.

For a more meaningful self-guided tour of the city's best attractions, visit Colosseum, a timeless archeological site that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Roman Forum and admire its culturally significant features.

When you’re ready, continue to Trevi Fountain, an iconic monument beloved by locals and tourists alike. Don't miss out on Pantheon, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Piazza Navona, a romantic place to see that you won’t regret spending some extra time discovering.

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

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.

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, including Montepulciano, San Quirico d'Orcia, and Montalcino. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

Fasten your seatbelt and make your way to your next stop — Montepulciano, home to many well-known sights in the region. Keep in mind that your travel time from Orvieto to Montepulciano may take around 1 hour 3 min without traffic disruptions. Upon arrival in Montepulciano, we highly recommend checking out some of the top attractions.

Our first attraction recommendation in Montepulciano is Fortezza Medicea, an up-and-coming castle that draws attention for its romantic features.

Fasten your seatbelt and make your way to your next stop — San Quirico d'Orcia, home to many well-known sights in the region. Keep in mind that your travel time from Montepulciano to San Quirico d'Orcia may take around 43 min without traffic disruptions. Upon arrival in San Quirico d'Orcia, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Cipressi Di San Quirico D'orcia, a frequently visited rock formation in San Quirico d'Orcia. Explore its serene features at your own pace before you continue your journey.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Montalcino. This drive usually takes around 20 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the town's best attractions, visit Fortress Of Montalcino, a worthwhile castle that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

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

Florence 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 Florence.

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!