9-Day Italy Self-Drive Road Trip With Itinerary from Rome to Florence, Siena, Greve in Chianti, and Perugia

Day 2 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Make sure to visit Trastevere, a popular neighborhood in Rome. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Spanish Steps is the first of them. Spend some time admiring this history-steeped public square before continuing your journey. Piazza Di Spagna is your next stop. This world-famous public square is one of the best-rated sights in Rome.

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 Trevi Fountain. This noteworthy monument is a sight to behold. To round off your sightseeing experience, visit Roman Forum and Colosseum.

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 Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

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

Round off your dining experience by visiting Sant' Eustachio Caffè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yellowsquare Rome, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 3 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, romantic experiences, and scenic views. Start at Piazzale Michelangelo, an impressive observation deck in the city. Then, head to Basilica Of Santa Croce In Florence and soak in the ambiance of this photogenic church.

There are many interesting places to see in Rome, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most top-rated eye-catching spots of interest. After exploring the art gallery, visit the globally renowned Ponte Vecchio. Not far away, you'll also find Piazza Della Repubblica. This public square is a romantic highlight in Rome. Before wrapping up your self-guided sightseeing tour, head to Piazza Della Signoria, an impressive public square in the city.

At the end of the day, you will drive to Florence, 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

Say good night to Florence and look forward to another great day of your road trip in Italy!

Greet day 4 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Leaning Tower Of Pisa. This timeless monument provides an insightful glimpse into the city's identity.

Continue your sightseeing with a visit to Piazza Del Duomo, Pisa, a timeless public square. When you’re done, don’t forget to make a stop at the underrated Pisa Cathedral. Not far away from the church, you will find the visually striking Mura Di Lucca, perfect for a quick visit. Round off your day at Porta San Pietro, another gem in Florence with breathtaking features to discover.

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

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

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.

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming city of Florence. Your adventure starts at Siena Cathedral, a well-known local hot spot. Another notable attraction to explore is Piazza Del Campo. This widely recognized public square is known for its romantic appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Tower Of Mangia. This historic monument offers a fascinating experience that many visitors find memorable. Parco Della Rocca is also worth visiting.

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.

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

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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 6 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Castellina in Chianti. At the end of the day, you will enjoy the comforts of a top-rated hotel in Greve in Chianti, which will be your home away from home for 1 night.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a castle, an archeological site, and a winery. Begin your adventure at Rocca Di Castellina In Chianti. This is an underrated castle you should not miss. Another must-see is Tumulo Di Montecalvario, a beloved archeological site in Siena.

When you’re ready for the next sight, head to Poggio Amorelli.

When you’re done exploring for the day, you’ll drive to your hotel in Greve in Chianti. 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 Greve in Chianti. 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.

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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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 Perugia. You’ll stay here for 1 night.

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

While exploring and sightseeing, take time to savor the culture of Greve in Chianti by sampling some local delicacies. When you’re ready for more sightseeing, head to Perugia Sotterranea Accesso. This historic cave system is an essential place to visit for anyone looking for the full Greve in Chianti experience. We also recommend visiting Perugia Cathedral, a beloved 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 breathtaking 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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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.

If you’re not ready to end the night just yet, Tommi Bar offers a perfect venue to relax and savor a drink. Similarly, Valentina is well-suited for those looking to unwind in a social setting. Caffe Dal Perugino is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Orvieto. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 1 night.

Perugia is brimming with adventures. Today’s wonderful stops include a church, a cave system, and a cave. Begin your sightseeing adventure at the interesting Orvieto Cathedral and allow yourself time to explore. Just a short distance away you'll find your next stop, Orvieto Underground, a history-steeped cave system that draws visitors from far and near.

Continue your journey to Pozzo Della Cava, one of the town’s most locally appreciated spots that you shouldn’t miss.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome 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 Rome's best restaurants.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

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