9-Day Italy Self-Drive Road Trip With Itinerary from Florence 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 well-planned self-sightseeing route offers several family-friendly attractions, 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 history-steeped observation deck before continuing your journey. Basilica Of Santa Croce In Florence is your next stop. This captivating 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.

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.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city 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 Pisa and Lucca.

Start by visiting Battistero Di San Giovanni, a prime spot to begin your journey. This UNESCO world heritage-listed church is sure to impress. Next on your list is Piazza Del Duomo, Pisa, another must-visit landmark and timeless public square renowned for its historic features.

While exploring and sightseeing, take time to savor the ambiance of Florence by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Leaning Tower Of Pisa. This UNESCO world heritage-listed monument is a remarkable attraction that offers a unique experience. Guinigi Tower also adds charm to your journey, and San Michele In Foro wraps up your day with its breathtaking appeal.

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

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.

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 fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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 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.

Florence is brimming with adventures. Today’s wonderful stops include a monument, a public square, a palace, a church and much more! Begin your sightseeing adventure at the curiosity-inducing Fortezza Medicea (siena). Just a short distance away is Tower Of Mangia, a respected monument that draws visitors from far and near.

Continue your journey to Piazza Del Campo, one of the city’s most impressive spots that you shouldn’t miss. Another great site to visit is the locally appreciated Pubblico Palace. Last up on today’s itinerary is a church. Make your way to Siena Cathedral for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of 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 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.

Make sure to reserve a table at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Savor another day of unforgettable experiences in Italy!

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

A blend of fun adventures, romantic experiences, and breathtaking views await you in Siena on today’s itinerary. First up is the often recommended winery, Poggio Amorelli. Afterward, continue to Tumulo Di Montecalvario.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Rocca Di Castellina In Chianti. This underrated castle is an essential stop that should not be missed.

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

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.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

After your meal, keep the night alive at a bar like Charlie Mixology Bar Di Aldinucci Riccardo, known for its lively atmosphere. Bar Pinacoteca is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, San Paolo Pub offers an excellent atmosphere for those looking to amp up the evening.

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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Basilica Of San Francesco D'assisi, a locally renowned church in the town. Then, head to Etruscan Well and soak in the ambiance of this heritage-rich archeological site.

There are many interesting places to see in Siena and when you are ready for more, go to Perugia Cathedral. This is one of the town’s most frequently visited spots. After exploring the church, visit the underrated Rocca Paolina. Before wrapping up your self-guided sightseeing tour, head to the worthwhile Piazza Iv Novembre, a worthwhile public square in the town.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Tommi Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Valentina offers an ideal atmosphere to enjoy the pleasures of the night. Caffe Dal Perugino is also a great option that provides a perfect setting for a relaxing evening.

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Orvieto and Sant'Angelo. At the end of the day, you will enjoy the comforts of a top-rated hotel in Orvieto, which will be your home away from home for 1 night.

Discover a day packed with family-friendly attractions, breathtaking views, and picturesque spots in Perugia. Begin your sightseeing with Well Of St. Patrick. This interesting monument is one of the top attractions in the village. Proceed to Orvieto Cathedral, another must-visit attraction that enhances the village’s allure.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Orvieto Underground. This curiosity-inducing cave system is a traveler-favorite. Not far away, you’ll find Torre Del Moro Orvieto, another key site on your sightseeing itinerary. Conclude your day at Pozzo Della Cava and uncover why it's recognized as one of the village's most intriguing attractions.

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.

Following your dinner, dive into the local bar culture at Bar Duomo. Enjoy this evening's relaxed ambiance with delightful drinks.

Raise your glass to another unforgettable day in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you will explore San Quirico d'Orcia and Montalcino, 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 Florence. You’ll stay here for 1 night.

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

After visiting Cipressi Di San Quirico D'orcia and Fortress Of Montalcino, take time to explore Orvieto's streets and absorb its charm. Continue your sightseeing by heading to Piazza Del Popolo. This romantic 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.

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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