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.

Trastevere is a neighborhood that stands out as one of the must-see places in Rome. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Today’s agenda in Rome includes a public square, a monument, and an archeological site. Spanish Steps is must-visit public square and a great starting point for the day. Next, continue your journey to Piazza Di Spagna, a wondrous public square, located just a leisurely stroll away. Next, head to Trevi Fountain, a history-steeped monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the timeless Roman Forum. If you’re looking for more, Colosseum is also a wondrous attraction that is worthwhile a visit.

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.

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

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.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Today, you'll explore some of the most beautiful places in Rome, including an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Start your day with a visit to Piazzale Michelangelo. This impressive observation deck is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of Santa Croce In Florence, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Rome on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Uffizi Gallery, a widely recognized art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Ponte Vecchio and Piazza Della Repubblica. End your day with a visit to Piazza Della Signoria, a top-rated public square that’s sure to leave a lasting impression.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Wake up to day 4 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the timeless Leaning Tower Of Pisa, a historic monument in Florence. Next, go to Putti Fountain.

After visiting Leaning Tower Of Pisa and Putti Fountain, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Duomo, Pisa. This historic public square offers a unique experience. Pisa Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Porta San Pietro, one of the most historic places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Mura Di Lucca.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences in Italy!

On day 5 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 1 night.

Florence is brimming with adventures. Today’s wonderful stops include a church, a public square, a monument, a park and much more! Begin your sightseeing adventure at the notable Siena Cathedral and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Del Campo, a history-steeped public square that draws visitors from far and near.

Continue your journey to Tower Of Mangia, one of the city’s most beloved spots that you shouldn’t miss. Another great site to visit is the underrated Parco Della Rocca.

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.

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

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.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Castellina in Chianti, 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 Greve in Chianti. You’ll stay here for 1 night.

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

Next, immerse yourself in the setting of Poggio Amorelli. Its romantic features will captivate you.

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

Raise your glass and celebrate another amazing day of your road trip 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 - 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.

Enjoy the perfect balance of relaxation and exploration in Greve in Chianti today. One of the most well-known attractions included on the itinerary is Basilica Of San Francesco D'assisi. This breathtaking church will help you start your sightseeing on top. Then, take a leisurely stroll to Rocca Maggiore and learn what makes this visually striking castle unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Perugia Sotterranea Accesso. After exploring the cave system, head to Perugia Cathedral. This beloved church is a highlight in Greve in Chianti. As your day continues, stop by Piazza Iv Novembre, known for its majestic features. Lastly, don’t forget to check out the frequently visited The Fontana Maggiore. Enjoy exploring this incredible monument at your own pace.

When you’re done exploring for the day, you’ll drive to your hotel in Perugia. Check in and spend some time relaxing before you head out to tour the city.

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.

Let the evening flow smoothly from dinner to drinks at Tommi Bar, a top-rated bar in the area. For other recommendations, Valentina provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffe Dal Perugino offers a memorable night with diverse drink options and excellent service.

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.

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 1 night.

Today’s agenda in Perugia includes a church, a cave system, and a cave. Orvieto Cathedral is must-visit church and a great starting point for the day. Next, continue your journey to Orvieto Underground, an often recommended cave system, located just a leisurely stroll away. Next, head to Pozzo Della Cava, an eye-catching cave, also available for your discovery today.

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.

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

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Unwind after your meal by stepping into The Apartment Bar Roma. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Hassler Roma offers a dynamic and energetic atmosphere for a glass or two.

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