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

Day 2 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in Florence by discovering the best things there are to see and do in the city.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Galleria Dell'accademia. This photogenic art gallery is a highlight of any visit in the city. Then, enjoy Piazza Della Signoria, another romantic attraction that never fails to captivate visitors. Next, head over to Ponte Vecchio, one of the city’s most timeless attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Uffizi Gallery. This standout art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Basilica Of Santa Croce In Florence, an interesting church, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazzale Michelangelo before you head back to your hotel.

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 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.

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.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

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

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Florence. Begin your sightseeing with Battistero Di San Giovanni. This frequently visited church is one of the top attractions in the city. Proceed to Piazza Del Duomo, Pisa, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Leaning Tower Of Pisa. This wondrous monument is a traveler-favorite. Not far away, you’ll find Guinigi Tower, another key site on your sightseeing itinerary. San Michele In Foro is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Mura Di Lucca and uncover why it's recognized as one of the city's most often recommended attractions.

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

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.

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.

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.

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

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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Siena Cathedral. This romantic church is a highlight of any visit in the city. Then, enjoy Piazza Del Campo, another respected attraction that never fails to captivate visitors. Next, head over to Tower Of Mangia, one of the city’s most increasingly popular attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Porta San Giovanni. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Sangimignano1300, a frequently visited museum, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Duomo before you head back to your hotel.

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent 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.

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, 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 and San Regolo. You still have 1 night left in Siena.

Savor the day by visiting some of the best places to see in Siena, including a castle and a winery. Start your adventure at Rocca Di Castellina In Chianti. This locally appreciated castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Poggio Amorelli located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Castello Di Brolio. Its history-steeped features will captivate you.

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

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

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

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.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 1 night.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most popular attractions included on the itinerary is Basilica Of San Francesco D'assisi. This picture-perfect church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Comune and learn what makes this symbolic public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Rocca Maggiore. After exploring the castle, head to Perugia Sotterranea Accesso. This curiosity-inducing cave system is a highlight in Siena. As your day continues, stop by The Fontana Maggiore, known for its historic features. Lastly, don’t forget to check out the curiosity-inducing Piazza Iv Novembre. Enjoy exploring this incredible public square at your own pace.

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.

As you explore more of Perugia, 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 Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Orvieto and Bolsena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Orvieto. You will spend 2 nights here for some well-deserved relaxation.

A blend of fun adventures, romantic experiences, and scenic views await you in Perugia on today’s itinerary. First up is the notable church, Orvieto Cathedral. Afterward, continue to Orvieto Underground, a cave system every traveler should visit.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the town. Next, make your way to Pozzo Della Cava. This often recommended cave is an essential stop. Following that, head to Basilica Of Santa Cristina, Bolsena, another must-visit site that will enhance your experience.

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.

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

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.

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

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Orvieto for your remaining 1 night in the town later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Rome.

Get ready to discover some of the most iconic wonders in Orvieto, including an archeological site, a monument, and a public square. Start your day at Colosseum. This picture-perfect archeological site is a globally renowned place to see in Orvieto. Then, wander over to Roman Forum. If historic sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Trevi Fountain. This history-steeped monument is a favorite among visitors.

Orvieto offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pantheon is a wondrous spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the symbolic Piazza Navona. Take a moment to appreciate the fascinating details of this iconic public square.

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

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.

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

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

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea. This frequently visited castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Cipressi Di San Quirico D'orcia, one of the town’s best highlights.

Next, check out Fortress Of Montalcino, one of the most up-and-coming places to see in Orvieto. This castle is a favorite among locals and travelers alike.

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.

Treat yourself to a wonderful meal at Tijuana, a top-rated dining spot in Florence. If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu. You might also want to book a table at The Florence Irish Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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