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

Day 2 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Experience Galleria Dell'accademia, a popular art gallery in the city. Then, head to Piazza Della Signoria and soak in the ambiance of this visually striking public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Ponte Vecchio. This is one of the city’s most world-famous romantic spots of interest. After exploring the historical landmark, visit the widely recognized Uffizi Gallery. Not far away, you'll also find Basilica Of Santa Croce In Florence. This church is a culturally significant highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazzale Michelangelo, an impressive observation deck in the city.

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.

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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. Known for great service, it’s a fantastic choice for tonight in Florence.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

On day 3 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary.

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 detailed monument.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Lucca may take around 32 min. Upon your arrival in Lucca, you’ll be greeted with the opportunity to do some sightseeing and exploring.

For a more meaningful self-guided tour of the city's best attractions, visit Guinigi Tower, a frequently visited 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.

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.

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. Known for great service, 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.

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 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.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Siena may take around 1 hour 12 min. Upon your arrival in Siena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Siena Cathedral is a well-known church we recommend visiting today. Discover its romantic features before continuing your self-guided tour to Piazza Del Campo, a romantic public square that’s well-regarded in the area.

Next, stop by Tower Of Mangia, a respected monument.

Set your GPS to San Gimignano and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Spend your afternoon discovering Porta San Giovanni, a locally appreciated monument known for its breathtaking features. Next, continue your sightseeing at Sangimignano1300, a locally appreciated museum.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Del Duomo and uncover the details of this inviting public square.

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 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.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists. Or, head to Maudit Pub. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Impero Siena, another top-rated place in the area.

Raise your glass to another unforgettable day in Italy!

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

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.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Castellina in Chianti. Expect your car journey to take a minimum of 31 min. When you arrive in Castellina in Chianti, it's time to take a break from the road.

Rocca Di Castellina In Chianti is a locally appreciated castle we recommend visiting today. Discover its romantic features before continuing your self-guided tour to Poggio Amorelli, an instagrammable winery that’s well-regarded in the area.

Set your GPS to San Regolo and hit the road. Expect a journey of approximately 38 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Regolo beckons with new experiences!

Savor the day by heading to Castello Di Brolio, an intriguing castle that draws visitors from near and far.

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 a true cultural experience.

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Fischi per Fiaschi? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your chosen hotel in Perugia, where you’ll be staying for 1 night.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Santa Maria degli Angeli. Your travel time is around 1 hour 36 min.

Savor the day by heading to Basilica Of San Francesco D'assisi, a well-known church that draws visitors from near and far. When you're done, continue to Piazza Del Comune, where you can soak in the grand surroundings.

Next, explore Rocca Maggiore, yet another increasingly popular place to see in the area.

Embrace the thrill of the open road as you wave goodbye to Santa Maria degli Angeli and set your GPS to Perugia. 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 32 min. Upon reaching Perugia, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

One of our top recommendations for your sightseeing is Perugia Sotterranea Accesso. Spend some time admiring the heritage-rich features of the cave system before you continue to your next stop. Then, head to The Fontana Maggiore. This worthwhile 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.

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.

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

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.

To truly maximize your evening out, consider visiting Tommi Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Valentina, another bar with an inviting ambiance. Similarly, Caffe Dal Perugino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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.

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.

Fasten your seatbelt and make your way to your next stop — Orvieto, home to many well-known sights in the region. Keep in mind that your travel time from Perugia to Orvieto may take around 1 hour 19 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Orvieto Cathedral, an interesting church that everyone visiting Orvieto should see. Next, head to Orvieto Underground. This respected cave system is one of the most up-and-coming attractions in the region.

If you're keen to see more, don’t miss out on Pozzo Della Cava, an instagrammable cave popular among locals as well as travelers.

Fasten your seatbelt and make your way to your next stop — Bolsena, home to many well-known sights in the region. Upon arrival in Bolsena, we highly recommend checking out some of the top attractions.

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, a curiosity-inducing 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.

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.

Unwind after your meal by stepping into Bar Duomo. This venue is celebrated for its extensive drink selections and cozy vibes.

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

On day 8 of your road trip, you'll get the chance to experience Rome. At the end of the day, you'll drive back to Orvieto, where you still have 1 night left to stay.

Continue your road trip and head to your next destination, Rome. This car ride takes around 1 hour 37 min.

Our first attraction recommendation in Rome is Colosseum, a globally renowned archeological site that draws attention for its picture-perfect features. Spend some time soaking in the atmosphere before continuing to Roman Forum, a culturally significant archeological site that stands out in the city.

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 Trevi Fountain, a world-famous monument that offers a unique experience. Be sure to also explore Pantheon, a nearby monument, highly recommended by other travelers. End your self-guided tour at Piazza Navona, a majestic public square and the perfect final attraction in Rome.

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.

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

On day 9 of your road trip in Italy, your travel plans include 3 stops at the most scenic, wondrous, and interesting places in the region. Montepulciano, San Quirico d'Orcia, and Montalcino are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Set your GPS to Montepulciano and hit the road. Expect a journey of approximately 1 hour 3 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Montepulciano beckons with new experiences!

Our first attraction recommendation in Montepulciano is Fortezza Medicea, a beloved castle that draws attention for its history-steeped features.

Continue your road trip and head to your next destination, San Quirico d'Orcia. This car ride takes around 43 min.

Our first attraction recommendation in San Quirico d'Orcia is Cipressi Di San Quirico D'orcia, an often recommended rock formation that draws attention for its mesmerizing features.

Montalcino’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of San Quirico d'Orcia behind. This drive usually takes around 20 min. Montalcino welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Fortress Of Montalcino. Spend some time admiring the visually striking features of the castle before you continue to your next stop.

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.

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.

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.

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