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.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. 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. Piazzale Michelangelo is the first of them. Spend some time admiring this visually striking observation deck before continuing your journey. Basilica Of Santa Croce In Florence is your next stop. This locally renowned church is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Uffizi Gallery. This romantic art gallery is a sight to behold. To round off your sightseeing experience, visit Ponte Vecchio and Piazza Della Signoria. If time allows, end your day with Galleria Dell'accademia, a detailed art gallery that offers a memorable conclusion to your exploration.

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.

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.

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

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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.

On day 3 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and photo-friendly spots. 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. Piazza Del Duomo, Pisa is the first of them. Spend some time admiring this UNESCO world heritage-designated public square before continuing your journey. Leaning Tower Of Pisa is your next stop. This iconic monument is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Guinigi Tower. This history-steeped monument is a sight to behold. To round off your sightseeing experience, visit 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.

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

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Gosh*, a well-loved spot among locals and tourists. Or, head to Antico Caffè Del Moro - Art Bar Firenze. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Quelo Bar, another top-rated place in the area.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

A blend of fun adventures, breathtaking views, and photo-friendly spots await you in Florence on today’s itinerary. First up is the up-and-coming monument, Fortezza Medicea (siena). Afterward, continue to Tower Of Mangia, a monument every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Del Campo. This extraordinary public square is an essential stop. Following that, head to Pubblico Palace, another must-visit site that will enhance your experience. Don’t forget to stop by Siena Cathedral, a locally renowned church in the city. Finally, end your day with a visit to Piazza Del Duomo, a visually striking public square that offers the perfect conclusion to your sightseeing of the day.

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.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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

Today’s itinerary in Siena covers several incredible sights, including a winery, an archeological site, and a castle. Start your adventure at Poggio Amorelli. This underrated winery is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the symbolic wonders of Tumulo Di Montecalvario, a must-see archeological site in the village.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Rocca Di Castellina In Chianti. This worthwhile castle offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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

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

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.

After enjoying a fulfilling meal, continue your evening at Charlie Mixology Bar Di Aldinucci Riccardo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Pinacoteca offers a welcoming atmosphere for easing into the nightlife. Similarly, San Paolo Pub provides an excellent environment for a relaxed and enjoyable evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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

Today’s itinerary in Siena covers several incredible sights, including a church, a castle, a historical landmark, a public square, a monument and much more! Start your adventure at Basilica Of San Francesco D'assisi. This captivating church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Rocca Maggiore, a must-see castle in the town.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Etruscan Arch. This worthwhile historical landmark offers an enriching experience. For a change of pace, head to Perugia Cathedral, where you can take in photogenic features. Conclude your self-guided sightseeing tour with a visit to Piazza Iv Novembre and The Fontana Maggiore. These sights offer a fulfilling end to a perfect day.

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.

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

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.

Continue the enjoyment post-dinner at Tommi Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Valentina offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffe Dal Perugino. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Prepare for a day full of fun adventures, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Well Of St. Patrick. This interesting monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Orvieto Cathedral, one of the village’s best highlights.

Next, check out Orvieto Underground, one of the most up-and-coming places to see in Perugia. This cave system is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Torre Del Moro Orvieto. Wander around and soak in the instagrammable atmosphere this monument offers. Then, head to Pozzo Della Cava, a top-rated cave that adds another dimension to your day. Finally, visit the underrated Il Paese Delle Fiabe, the last of our attraction recommendations for today.

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

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

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

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

On day 8 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 San Quirico d'Orcia and Montalcino. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and natural wonders. Start at the up-and-coming Cipressi Di San Quirico D'orcia, an idyllic rock formation in Orvieto. Next, go to Fortress Of Montalcino.

After visiting Cipressi Di San Quirico D'orcia and Fortress Of Montalcino, have a stroll along Orvieto's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Popolo. This instagrammable public square offers a unique experience.

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 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 and reflect on the day'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.

Savor another day of unforgettable experiences in Italy!