9-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.

Florence is brimming with adventures. Today’s wonderful stops include an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Begin your sightseeing adventure at the top-rated Piazzale Michelangelo. Just a short distance away is Basilica Of Santa Croce In Florence, a photogenic church that draws visitors from far and near.

Continue your journey to Uffizi Gallery, one of the city’s most famous spots that you shouldn’t miss. Another great site to visit is the wondrous Ponte Vecchio. Last up on today’s itinerary is a public square. Make your way to Piazza Della Signoria for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Florence.

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.

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

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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences in Italy!

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

Today, you'll explore some of the most beautiful places in Florence, including a public square, a monument, a church, a historical landmark and much more! Start your day with a visit to Piazza Del Duomo, Pisa. This timeless public square is a must-visit in the city. When you’re ready for your next discovery, continue to Leaning Tower Of Pisa, which may be one of the most culturally significant 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 Guinigi Tower, an intriguing monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for San Michele In Foro and Mura Di Lucca.

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

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

Treat yourself to a delightful dinner at Ristorante Buca Mario, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Agricola Toscana? It's another excellent option with a diverse menu. Consider reserving a table at Eataly Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Continue your lively evening at Gosh*, a perfect place for winding down or revving up the night, depending on which mood you’re in. Antico Caffè Del Moro - Art Bar Firenze is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Quelo Bar ensures a night out tailored to your taste.

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

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

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the increasingly popular Fortezza Medicea (siena), a culturally significant monument in Florence. Next, go to Tower Of Mangia.

After visiting Fortezza Medicea (siena) and Tower Of Mangia, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Piazza Del Campo. This enchanting public square offers a unique experience. Pubblico Palace is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Siena Cathedral, one of the most culturally significant places to visit in Florence.

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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

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

On day 5 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. You still have 1 night left in Siena.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most curiosity-inducing attractions included on the itinerary is Poggio Amorelli. This visually striking winery will help you start your sightseeing on top. Then, take a leisurely stroll to Tumulo Di Montecalvario and learn what makes this symbolic archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Rocca Di Castellina In Chianti.

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 and reflect on the day's adventures.

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. 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 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.

Savor another day of unforgettable experiences in Italy!

On day 6 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 Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Discover a day packed with fun adventures, scenic views, and picturesque spots in Siena. Begin your sightseeing with Basilica Of San Francesco D'assisi. This locally renowned church is one of the top attractions in the town. Proceed to Rocca Maggiore, another must-visit attraction that enhances the town’s allure.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Etruscan Arch. This locally appreciated historical landmark is a traveler-favorite. Not far away, you’ll find Perugia Cathedral, another key site on your sightseeing itinerary. Conclude your day at Piazza Iv Novembre and uncover why it's recognized as one of the town's most up-and-coming attractions.

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

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

Treat yourself to a delicious dinner at Ristorante Settimo Sigillo, an excellent option for tonight's dining. Looking for something different? Caffè Baglioni offers a tantalizing alternative with its diverse menu. And don’t miss Bar Pellas. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

After savoring a delicious meal, step into the vibrant nightlife at Tommi Bar, where the evening is just getting started. In the same way, Valentina offers a unique charm perfect for experiencing the local bar scene in Perugia. Caffe Dal Perugino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Orvieto and Sant'Angelo, 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 Orvieto. You’ll stay here for 1 night.

A blend of family-friendly attractions, scenic views, and picturesque spots await you in Perugia on today’s itinerary. First up is the captivating monument, Well Of St. Patrick. Afterward, continue to Orvieto Cathedral, a church every traveler should visit.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Orvieto Underground. This often recommended cave system is an essential stop. Following that, head to Torre Del Moro Orvieto, another must-visit site that will enhance your experience. Don’t forget to stop by Pozzo Della Cava, a worthwhile cave in the village. Finally, end your day with a visit to Il Paese Delle Fiabe, an eye-catching art installation that offers the perfect conclusion to your sightseeing of the day.

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.

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

Continue the enjoyment post-dinner at Bar Duomo, a cherished local gathering spot renowned for its welcoming atmosphere.

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

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of San Quirico d'Orcia and Montalcino. 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.

Orvieto is home to plenty of attractions that offer fun adventures, romantic experiences, and natural wonders! Start at Cipressi Di San Quirico D'orcia, a beloved rock formation that is worthwhile a visit in the town. Nearby, you’ll find Fortress Of Montalcino, enchanting visitors with its history-steeped appeal. Continue your exploration at Piazza Del Popolo. This public square is one of the town’s most up-and-coming spots.

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.

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.

Dine in style at Tijuana, a top recommendation for dinner tonight. Or, for a change of pace, Djària - American Bar boasts a menu that's sure to impress. Also, be sure to check out The Florence Irish Pub. Known as a local hotspot, it’s a great choice for tonight in Florence.

Savor another day of unforgettable experiences in Italy!