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

On day 2 of your road trip in Italy, you’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 1 night more, there’s no need to rush. Experience Rome and Vatican City to the fullest today with this curated day itinerary!

A top thing to do today is to explore Trastevere, a must-see neighborhood in Rome. It's the perfect starting point for exploring the top attractions in the area.

Start your adventure at Spanish Steps. This famous 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 an enchanting atmosphere.

Next, immerse yourself in the setting of Trevi Fountain. Its visually striking features will captivate you. After the monument, continue your tour of the city with a visit to Pantheon. This monument has an instagrammable appeal. For a change of pace, head to Roman Forum. As one of the most iconic attractions in Rome, this archeological site is an excellent place to end your self-guided tour.

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

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 and reflect on the day'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.

Continue your lively evening at Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Florence, 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 Florence. You’ll stay here for 2 nights.

Rome is brimming with adventures. Today’s wonderful stops include a botanical garden, an observation deck, a church, an art gallery, a historical landmark and much more! Begin your sightseeing adventure at the popular The Boboli Gardens. Just a short distance away is Piazzale Michelangelo, a visually striking observation deck that draws visitors from far and near.

Continue your journey to Basilica Of Santa Croce In Florence, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the astonishing Uffizi Gallery. Last up on today’s itinerary is a historical landmark. Make your way to Ponte Vecchio for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Rome.

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 explore more of Florence, 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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Florence is brimming with adventures. Today’s wonderful stops include a public square, a church, a monument, a museum, a historical landmark and much more! Begin your sightseeing adventure at the iconic Piazza Del Duomo, Pisa. Just a short distance away is Pisa Cathedral, a breathtaking church that draws visitors from far and near.

Continue your journey to Leaning Tower Of Pisa, one of the city’s most wondrous spots that you shouldn’t miss. Another great site to visit is the increasingly popular Museo Dell'opera Del Duomo. Last up on today’s itinerary is a historical landmark. Make your way to Mura Di Lucca for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Florence.

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

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.

Enjoy a lovely dining experience at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Florence is home to plenty of attractions that offer fun adventures, scenic views, and photo-friendly spots! Start at Fortezza Medicea (siena), an increasingly popular monument that is worthwhile a visit in the city. Nearby, you’ll find Tower Of Mangia, enchanting visitors with its UNESCO world heritage-designated appeal. Continue your exploration at Piazza Del Campo. This public square is one of the city’s most top-rated 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 beloved Parco Della Rocca. This park will wrap up today’s self-guided sightseeing tour in the city.

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 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.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, 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 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Castellina in Chianti and Greve in Chianti. At the end of the day, you will enjoy the comforts of a top-rated hotel in Montefioralle, which will be your home away from home for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the beloved Rocca Di Castellina In Chianti, a visually striking castle in Siena. Next, go to Poggio Amorelli.

After visiting Rocca Di Castellina In Chianti and Poggio Amorelli, take time to explore Siena's streets and absorb its charm. Continue your sightseeing by heading to Castle Of Verrazzano. This instagrammable castle offers a unique experience.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Montefioralle. If you are looking to dine at a popular restaurant in the village, it's often a good idea to reserve a table in advance.

Dine in style at La Castellana, a top recommendation for dinner tonight.

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

Enjoy the perfect balance of relaxation and exploration in Montefioralle today. One of the most locally renowned attractions included on the itinerary is Basilica Of San Francesco D'assisi. This historic church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Comune and learn what makes this history-steeped public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Rocca Maggiore. After exploring the castle, head to Rocca Paolina. This underrated historical landmark is a highlight in Montefioralle. Lastly, don’t forget to check out the often recommended Perugia Cathedral. Enjoy exploring this incredible church 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.

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

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.

Round off your dining experience by visiting Tommi Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Valentina, a bar catering to every mood and preference. Caffe Dal Perugino likewise offers a unique atmosphere, perfect for a memorable night out.

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 8 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 Orvieto. In the evening, you’ll end up in Rome, where you will stay for 1 night.

Brace yourself for today’s incredible lineup of attractions in Perugia, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Well Of St. Patrick, a locally renowned monument in the village. Then, head to Orvieto Cathedral and soak in the ambiance of this enchanting church.

There are many interesting places to see in Perugia and when you are ready for more, go to Orvieto Underground. This is one of the village’s most beloved spots. After exploring the cave system, visit the up-and-coming Torre Del Moro Orvieto. Before wrapping up your self-guided sightseeing tour, head to the underrated Pozzo Della Cava, an underrated cave in the village.

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 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 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.

Raise your glass to another unforgettable day in Italy!