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

On day 2 of your road trip, you’ll start and end your day in Rome, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Rome and Vatican City. You still have 1 night left in Rome.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Begin your adventure at Spanish Steps. This is a spectacular public square you should not miss. Another must-see is Piazza Di Spagna, a wondrous public square in Rome.

When you’re ready for the next sight, head to Trevi Fountain. From there, take a leisurely stroll to Pantheon, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Roman Forum, a culturally significant place of interest in the city. If time allows, add Colosseum to your itinerary. This wondrous archeological site offers the perfect finishing touch to your day in Rome.

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

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.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

Take some time to reflect on your day and savor another beautiful night 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 for an exciting day in Rome. Today’s sightseeing agenda includes a botanical garden, an observation deck, a church, an art gallery, a historical landmark and much more! Begin your adventure at The Boboli Gardens. This is an interesting botanical garden you should not miss. Another must-see is Piazzale Michelangelo, a famous observation deck in Rome.

When you’re ready for the next sight, head to Basilica Of Santa Croce In Florence. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s spectacular attractions. We recommend continuing your self-guided tour at Ponte Vecchio, a visually striking place of interest in the city.

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

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day 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.

Florence is home to plenty of attractions that offer fun adventures, scenic views, and photo-friendly spots! Start at Piazza Del Duomo, Pisa, a wondrous public square that is worthwhile a visit in the city. Nearby, you’ll find Pisa Cathedral, enchanting visitors with its culturally significant appeal. Continue your exploration at Leaning Tower Of Pisa. This monument is one of the city’s most wondrous 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 Museo Dell'opera Del Duomo. After exploring the museum, head to the increasingly popular Mura Di Lucca. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Dell'anfiteatro, a place of stunning interest in Florence.

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

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

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.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Fortezza Medicea (siena). This intriguing monument provides an insightful glimpse into the city's identity. Next, discover Tower Of Mangia, a culturally significant monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Del Campo, a famous public square. When you’re done, don’t forget to make a stop at the notable Siena Cathedral. Not far away from the church, you will find the romantic Piazza Del Duomo, perfect for a quick visit. Round off your day at Parco Della Rocca, another gem in Florence with enchanting features to discover.

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.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 6 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 Castellina in Chianti and Greve in Chianti. In the evening, you’ll end up in Montefioralle, where you will stay for 1 night.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Rocca Di Castellina In Chianti. This enchanting castle is sure to ignite your curiosity. Next, dive into the enchanting features of Poggio Amorelli, a must-visit winery 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 Castle Of Verrazzano, an up-and-coming castle.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Montefioralle. Montefioralle 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 Montefioralle. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at La Castellana, highly recommended for tonight's dining.

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

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

Savor the day by visiting some of the best places to see in Montefioralle, including a church, a public square, a castle, a historical landmark and much more! Start your adventure at Basilica Of San Francesco D'assisi. This notable church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Comune located in Montefioralle for another exciting encounter.

Next, immerse yourself in the setting of Rocca Maggiore. Its history-steeped features will captivate you. After the castle, continue your tour of the town with a visit to Rocca Paolina. Visitors usually appreciate the symbolic features of this historical landmark. Next up is Perugia Cathedral, a highly recommended church. For a change of pace, head to Piazza Iv Novembre. As one of the most beloved attractions in Montefioralle, this public square is the perfect place to end your self-guided sightseeing tour.

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.

Treat yourself to a wonderful meal at Ristorante Settimo Sigillo, a top-rated dining spot in Perugia. If you're in the mood for something new, try Caffè Baglioni, another premier location with a delectable menu. You might also want to book a table at Bar Pellas. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

Raise your glass and celebrate another amazing day 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.

Set out on a day brimming with family-friendly attractions, breathtaking views, and picturesque spots. Start at the well-known Well Of St. Patrick, a breathtaking monument in Perugia. Next, go to Orvieto Cathedral.

After visiting Well Of St. Patrick and Orvieto Cathedral, have a stroll along Perugia's streets and take in the local charm. Continue your sightseeing by heading to Orvieto Underground. This eye-catching cave system offers a unique experience. Torre Del Moro Orvieto is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Pozzo Della Cava, one of the most instagrammable places to visit in Perugia.

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.

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 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 fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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