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

Day 2 of your road trip across Italy promises a magnificent time exploring what to see in Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

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. 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.

Look forward to a unique sightseeing adventure at the top-rated Spanish Steps and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Di Spagna, a romantic public square that draws visitors from far and near.

Continue your journey to Trevi Fountain, one of the city’s most iconic spots that you shouldn’t miss. Another great site to visit is the iconic Roman Forum. When you're finished at the archeological site, Colosseum awaits your visit. This archeological site is a historic highlight on today's itinerary.

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.

For an unforgettable shopping experience, visit Trastevere, the top shopping destination in Rome. Browse local boutique shops and stores, each offering delightful surprises. Find unique souvenirs or items to take home, including artisan crafts. After shopping, explore what Trastevere has to offer, including attractions, essential services, and vibrant community activities.

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

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining 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.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Florence may take around 3 hours 6 min. Upon your arrival in Florence, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Set out on a self-guided sightseeing tour at Piazzale Michelangelo and explore the enchanting features. Next, make your way to Basilica Of Santa Croce In Florence, another highlight in Florence. When you’re done exploring the church, continue to Uffizi Gallery, a respected art gallery.

Nearby, you will also find Ponte Vecchio. This wondrous historical landmark is a top place to see in the area. Lastly, head to Piazza Della Repubblica, a romantic public square that is perfect for some final exploring in the city.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San 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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 4 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Pisa’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 18 min. Pisa welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Leaning Tower Of Pisa. Spend some time admiring the UNESCO world heritage-listed features of the monument before you continue to your next stop. Then, head to Putti Fountain. This increasingly popular fountain is a traveler-favorite in the city.

If you're keen to see more, continue to Piazza Del Duomo, Pisa. Feed your curiosity by learning something new about the public square. Next, take your journey to Pisa Cathedral, an up-and-coming church.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Lucca may take around 27 min. Upon your arrival in Lucca, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Porta San Pietro. Spend some time admiring the historic features of the monument before you continue to your next stop. Then, head to Mura Di Lucca. This locally appreciated historical landmark is a traveler-favorite in the city.

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

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass to another unforgettable day in Italy!

On day 5 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Gimignano are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 1 night.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 12 min.

Our first attraction recommendation in Siena is Siena Cathedral, a well-known church that draws attention for its romantic features. Spend some time soaking in the atmosphere before continuing to Piazza Del Campo, a visually striking public square that stands out in the city.

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 Tower Of Mangia, a locally appreciated monument that offers a unique experience.

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!

Set out on a self-guided sightseeing tour at Parco Della Rocca and explore the romantic features.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Castellina in Chianti. When you’re not sightseeing, take time to relax at your chosen hotel in Greve in Chianti, where you’ll be staying for 1 night.

Continue your road trip and head to your next destination, Castellina in Chianti. This car ride takes around 31 min.

Savor the day by heading to Rocca Di Castellina In Chianti, a beloved castle that draws visitors from near and far. When you're done, continue to Tumulo Di Montecalvario, where you can soak in the heritage-rich surroundings.

Next, explore Poggio Amorelli, yet another increasingly popular place to see in the area.

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.

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

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

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Santa Maria degli Angeli and Perugia. At the end of the day, you’ll unwind at one of the finest accommodations in Perugia, where you'll spend 1 night.

After soaking in Greve in Chianti’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Santa Maria degli Angeli. Expect your car journey to take a minimum of 2 hours 10 min. When you arrive in Santa Maria degli Angeli, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Basilica Of San Francesco D'assisi, a well-known church that everyone visiting Santa Maria degli Angeli should see. Next, head to Rocca Maggiore. This romantic castle is one of the most curiosity-inducing attractions in the region.

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.

Our first attraction recommendation in Perugia is Perugia Sotterranea Accesso, an underrated cave system that draws attention for its respected features. Spend some time soaking in the atmosphere before continuing to Perugia Cathedral, a culturally significant church that stands out in the town.

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 Piazza Iv Novembre, a locally appreciated public square that offers a unique experience. Be sure to also explore The Fontana Maggiore, a nearby monument, highly recommended by other travelers.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Perugia. Perugia 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 Perugia, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Perugia tonight.

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

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Orvieto. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Perugia and set your GPS to Orvieto. 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 1 hour 19 min. Upon reaching Orvieto, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Spend your afternoon discovering Orvieto Cathedral, an interesting church known for its culturally significant features. Next, continue your sightseeing at Orvieto Underground, an increasingly popular cave system.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Pozzo Della Cava and uncover the details of this visually striking cave.

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

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

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