9-Day Italy Self-Drive Road Trip With Itinerary from Rome traveling west to Florence, Siena, Montefioralle, and Perugia

Wake up to day 2 of your extraordinary road trip in Italy. With 1 night left in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

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.

Start your adventure at Spanish Steps. This spectacular public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Di Spagna located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Trevi Fountain. Its detailed features will captivate you. After the monument, continue your tour of the city with a visit to Pantheon. Visitors usually appreciate the standout features of this monument. Next up is Roman Forum, a highly recommended archeological site. For a change of pace, head to Colosseum. As one of the most wondrous attractions in Rome, this archeological site is the perfect place to end your self-guided sightseeing tour.

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

As you explore more of Rome, 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.

Don’t miss out on dining 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.

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 to another unforgettable day in Italy!

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Get ready to discover some of the most iconic wonders in Rome, including a botanical garden, an observation deck, a church, an art gallery, a historical landmark and much more! Start your day at The Boboli Gardens. This romantic botanical garden is a well-known place to see in Rome. Then, wander over to Piazzale Michelangelo. If romantic sites excite you, this observation deck will be right up your alley. Nearby, you’ll also find Basilica Of Santa Croce In Florence. This standout church is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Uffizi Gallery is an extraordinary spot in the city that will captivate you with its unique charm. When you’re done at the art gallery, don’t forget to check out the symbolic Ponte Vecchio. Take a moment to appreciate the fascinating details of this iconic historical landmark.

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.

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 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.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo, Pisa. This grand public square is a highlight of any visit in the city. Then, enjoy Pisa Cathedral, another historic attraction that never fails to captivate visitors. Next, head over to Leaning Tower Of Pisa, one of the city’s most iconic attractions, known for its detailed features.

If you’re looking for more, spend time soaking in the atmosphere of Museo Dell'opera Del Duomo. This heritage-rich museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Mura Di Lucca, a frequently visited historical landmark, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Dell'anfiteatro before you head back to your hotel.

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

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.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.

Raise your glass and celebrate another amazing day of your road trip 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 home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Fortezza Medicea (siena), a locally appreciated monument that is worthwhile a visit in the city. Nearby, you’ll find Tower Of Mangia, enchanting visitors with its breathtaking appeal. Continue your exploration at Piazza Del Campo. This public square is one of the city’s most extraordinary spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Siena Cathedral. After exploring the church, head to the locally appreciated Parco Della Rocca. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Del Duomo, a place of inviting interest in 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.

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 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.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Castellina in Chianti and Greve in Chianti. When you’re not sightseeing, take time to relax at your selected hotel in Montefioralle, where you’ll be staying for 1 night.

Today’s itinerary in Siena covers several incredible sights, including a castle and a winery. Start your adventure at Rocca Di Castellina In Chianti. This beloved castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the instagrammable wonders of Poggio Amorelli, a must-see winery in the village.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Castle Of Verrazzano. This increasingly popular castle offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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

Savor the flavors at La Castellana, a top pick for dinner tonight.

Raise your glass to another unforgettable day 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.

Get ready for a day filled with fun adventures, scenic views, and photo-friendly spots in the charming town of Montefioralle. Your adventure starts at Basilica Of San Francesco D'assisi, a notable local hot spot. Another notable attraction to explore is Piazza Del Comune. This worthwhile public square is known for its stunning appeal.

After soaking in the highlights of these sights, take some time to wander Montefioralle's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Rocca Maggiore. This history-steeped castle offers a fascinating experience that many visitors find memorable. Rocca Paolina is also worth visiting, along with Perugia Cathedral. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Iv Novembre. This underrated public square provides a fitting finale to your sightseeing.

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 explore more of Perugia, 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.

Treat yourself to a delightful dinner at Ristorante Settimo Sigillo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Caffè Baglioni? It's another excellent option with a diverse menu. Consider reserving a table at Bar Pellas as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

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

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 8 of your remarkable road trip in Italy. Today you will explore Orvieto, 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 Rome. You’ll stay here for 1 night.

Immerse yourself in Perugia’s rich culture with today's sightseeing itinerary. Start your journey at Well Of St. Patrick. This breathtaking monument is sure to ignite your curiosity. Next, dive into the grand features of Orvieto Cathedral, a must-visit church in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Orvieto Underground, an up-and-coming cave system. For a change of scene, check out Torre Del Moro Orvieto, known for its culturally significant features. We also recommend visiting Pozzo Della Cava. This cave is a must for anyone looking to experience the village to the fullest.

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.

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

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

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