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

Day 2 offers an itinerary packed with the best things to see in Rome. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Don’t miss Trastevere today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

One of the most widely recognized attractions included on the itinerary is Spanish Steps. This enchanting public square will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Di Spagna and learn what makes this enchanting public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the world-famous Trevi Fountain. After exploring the monument, head to Roman Forum. This wondrous archeological site is a highlight in Rome. As your day continues, stop by Colosseum, known for its UNESCO world heritage-designated features.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine.

Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

Continue your road trip and head to your next destination, Florence. This car ride takes around 3 hours 6 min.

One of our top recommendations for your sightseeing is Piazzale Michelangelo. Spend some time admiring the respected features of the observation deck before you continue to your next stop. Then, head to Basilica Of Santa Croce In Florence. This interesting church is a traveler-favorite in the city.

If you're keen to see more, continue to Uffizi Gallery. Feed your curiosity by learning something new about the art gallery. Next, take your journey to Ponte Vecchio, a timeless historical landmark. Conclude your sightseeing at Piazza Della Repubblica, known for its romantic features.

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.

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

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day in Italy!

On day 4 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary.

Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 1 hour 18 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Leaning Tower Of Pisa is a world-famous monument we recommend visiting today. Discover its UNESCO world heritage-listed features before continuing your self-guided tour.

Next, stop by Piazza Del Duomo, Pisa, an UNESCO world heritage-listed public square. While you’re nearby, don’t forget to visit Pisa Cathedral, a stunning and truly unique church.

Lucca’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 27 min. Lucca welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Porta San Pietro, a frequently visited monument that draws visitors from near and far. When you're done, continue to Mura Di Lucca, where you can soak in the enchanting surroundings.

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

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.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Siena and San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 1 night.

Siena’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 12 min. Siena welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Siena Cathedral, a well-known church that draws visitors from near and far. When you're done, continue to Piazza Del Campo, where you can soak in the history-steeped surroundings.

Next, explore Tower Of Mangia, yet another intriguing place to see in the area.

Set your GPS to San Gimignano and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Savor the day by heading to Parco Della Rocca, an intriguing park that draws visitors from near and far.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

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.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

Take some time to reflect on your day and savor another beautiful night 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 1 place, which are Castellina in Chianti. At the end of the day, you will retreat to the hotel of your choice in Greve in Chianti, where will spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Castellina in Chianti. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 31 min. Upon reaching Castellina in Chianti, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Our first attraction recommendation in Castellina in Chianti is Rocca Di Castellina In Chianti, a frequently visited castle that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to Tumulo Di Montecalvario, an instagrammable archeological site that stands out in the village.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Poggio Amorelli, an underrated winery that offers a unique experience.

When you’re done exploring for the day, you’ll drive to your hotel in Greve in Chianti. Check in and relax before you head out to tour the town.

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

Savor another day of unforgettable experiences in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your chosen hotel in Perugia, where you’ll be staying for 1 night.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Santa Maria degli Angeli. This drive usually takes around 2 hours 10 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the town's best attractions, visit Basilica Of San Francesco D'assisi, a captivating church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Rocca Maggiore and admire its visually striking features.

When you’ve had your share of Santa Maria degli Angeli, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Perugia. Your travel time is around 32 min.

Set out on a self-guided sightseeing tour at Perugia Sotterranea Accesso and explore the heritage-rich features. Next, make your way to Perugia Cathedral, another highlight in Perugia. When you’re done exploring the church, continue to Piazza Iv Novembre, an enchanting public square.

Nearby, you will also find The Fontana Maggiore. This frequently visited monument is a top place to see in the area.

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.

Savor the flavors at Ristorante Settimo Sigillo, a top pick for dinner tonight. Alternatively, Caffè Baglioni beckons with its unique menu offerings. Also, consider Bar Pellas. With its consistent customer satisfaction, it’s an excellent option for dining in Perugia tonight.

Following your dinner, dive into the local bar culture at Tommi Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Valentina, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffe Dal Perugino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Orvieto are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 1 night.

Fasten your seatbelt and make your way to your next stop — Orvieto, home to many well-known sights in the region. Keep in mind that your travel time from Perugia to Orvieto may take around 1 hour 19 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Orvieto Cathedral, a notable church that everyone visiting Orvieto should see. Next, head to Orvieto Underground. This standout cave system is one of the most worthwhile attractions in the region.

If you're keen to see more, don’t miss out on Pozzo Della Cava, an instagrammable cave popular among locals as well as travelers.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

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