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

Day 2 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Begin your adventure at Piazzale Michelangelo. This is a top-rated observation deck you should not miss. Another must-see is Basilica Of Santa Croce In Florence, a captivating church in Florence.

When you’re ready for the next sight, head to Uffizi Gallery. From there, take a leisurely stroll to Ponte Vecchio, another of the city’s globally renowned attractions. We recommend continuing your self-guided tour at Piazza Della Signoria, a history-steeped place of interest in the city. If time allows, add Galleria Dell'accademia to your itinerary. This captivating art gallery offers the perfect finishing touch to your day in 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.

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 Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. 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 Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a public square, a monument, a church, a historical landmark and much more! Begin your adventure at Piazza Del Duomo, Pisa. This is a wondrous public square you should not miss. Another must-see is Leaning Tower Of Pisa, an iconic monument in Florence.

When you’re ready for the next sight, head to Guinigi Tower. From there, take a leisurely stroll to San Michele In Foro, another of the city’s locally appreciated attractions. We recommend continuing your self-guided tour at Mura Di Lucca, a romantic place of interest in the city.

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.

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. 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 Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

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

On day 4 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 Siena and San Gimignano. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a public square, a palace, a church and much more! Begin your adventure at Fortezza Medicea (siena). This is an underrated monument you should not miss. Another must-see is Tower Of Mangia, an underrated monument in Florence.

When you’re ready for the next sight, head to Piazza Del Campo. From there, take a leisurely stroll to Pubblico Palace, another of the city’s intriguing attractions. We recommend continuing your self-guided tour at Siena Cathedral, a visually striking place of interest in the city. If time allows, add Piazza Del Duomo to your itinerary. This curiosity-inducing public square offers the perfect finishing touch to your day 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.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Maudit Pub is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Impero Siena ensures a night out tailored to your taste.

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

On day 5 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Today’s agenda in Siena includes a winery, an archeological site, and a castle. Poggio Amorelli is must-visit winery and a great starting point for the day. Next, continue your journey to Tumulo Di Montecalvario, a worthwhile archeological site, located just a leisurely stroll away. Next, head to Rocca Di Castellina In Chianti, a respected castle, also available for your discovery today.

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

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

Make sure to reserve a table at Osteria Quattro Venti, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Fischi per Fiaschi, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Santa Maria degli Angeli and Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

Start by visiting Basilica Of San Francesco D'assisi, a prime spot to begin your journey. This picture-perfect church is sure to impress. Next on your list is Rocca Maggiore, another must-visit landmark and up-and-coming castle renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Etruscan Arch. This historic historical landmark is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Perugia Cathedral, an underrated church. Nearby, you'll also find Piazza Iv Novembre, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at The Fontana Maggiore and wrap up your day with its picture-perfect appeal.

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.

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

Enjoy a delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

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.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Orvieto and Sant'Angelo. When you’re not sightseeing, take time to relax at your selected hotel in Orvieto, where you’ll be staying for 1 night.

Enjoy the perfect balance of relaxation and exploration in Perugia today. One of the most popular attractions included on the itinerary is Well Of St. Patrick. This picture-perfect monument will help you start your sightseeing on top. Then, take a leisurely stroll to Orvieto Cathedral and learn what makes this enchanting church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Orvieto Underground. After exploring the cave system, head to Torre Del Moro Orvieto. This curiosity-inducing monument is a highlight in Perugia. As your day continues, stop by Pozzo Della Cava, known for its heritage-rich features. Lastly, don’t forget to check out the locally appreciated Il Paese Delle Fiabe. Enjoy exploring this incredible art installation at your own pace.

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.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Duomo, known for its inviting atmosphere.

Raise your glass and celebrate another amazing day of your road trip 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.

Today’s route brings family-friendly attractions, romantic experiences, and natural wonders. The first attraction of today is Cipressi Di San Quirico D'orcia. This frequently visited rock formation is a serene place to see in Orvieto. Continue your discovery at Fortress Of Montalcino, a majestic castle with stories to tell.

As you stroll around Orvieto, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Piazza Del Popolo. This often recommended public square offers a visually striking encounter with Orvieto. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Orvieto.

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 explore more of Florence, 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.

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.

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