11-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling south to Bologna, Florence, San Gimignano, Rome, and Naples

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Rimini and Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Enjoy the perfect balance of relaxation and exploration in Rimini today. One of the most notable attractions included on the itinerary is Arch Of Augustus. This culturally significant monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Santo Stefano 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 interesting Two Towers. After exploring the monument, head to Bologna Cathedral. This often recommended church is a highlight in Rimini. As your day continues, stop by Piazza Maggiore, known for its enchanting features.

At the end of the day, you will drive to Bologna, 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 Bologna's most popular restaurants, and connect with friendly locals for an authentic adventure.

Have a fantastic dining experience at Ristorante Ciacco, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Ballarini offers an enticing alternative with its varied menu. Additionally, Sfoglia Rina is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

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

On day 3 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! The Boboli Gardens is the perfect place to start. This botanical garden is one of the most captivating places to visit in Bologna. Next, head to Ponte Vecchio, a wondrous historical landmark, known for its history-steeped features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Uffizi Gallery. This romantic art gallery is a highly recommended experience. Nearby, you'll also find Basilica Of Santa Croce In Florence and Palazzo Vecchio. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Della Signoria, an enchanting public square in Bologna.

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

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.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

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

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!

Continue your journey to Pisa Cathedral, one of the city’s most intriguing spots that you shouldn’t miss. Another great site to visit is the curiosity-inducing Campo Santo. When you're finished at the cemetery, Piazza Del Duomo, Pisa awaits your visit. This public square is a majestic highlight on today's itinerary.

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 delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in San Gimignano, which will be your home away from home for 2 nights.

Savor the day by visiting some of the best places to see in Florence, including a church, a public square, a monument, a museum and much more! Start your adventure at Siena Cathedral. This locally renowned church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Campo located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Tower Of Mangia. Its historic features will captivate you. After the monument, continue your tour of the city with a visit to Sangimignano1300. Visitors usually appreciate the historic features of this museum. Next up is Piazza Del Duomo, a highly recommended public square.

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

As you explore more of San Gimignano, 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.

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

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to San Gimignano for your remaining 1 night in the village 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 San Regolo and Castellina in Chianti.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Castello Di Brolio. This underrated castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Tumulo Di Montecalvario, one of the hamlet’s best highlights.

Next, check out Rocca Di Castellina In Chianti, one of the most worthwhile places to see in San Gimignano. This castle is a favorite among locals and travelers alike.

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

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

Get a good night's sleep and look forward to another great day on the road in Italy!

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Rome, 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 2 nights.

San Gimignano is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Castel Sant'angelo, an astonishing castle that is worthwhile a visit in the city. Nearby, you’ll find Piazza Navona, enchanting visitors with its remarkable appeal. Continue your exploration at Spanish Steps. This public square is one of the city’s most astonishing spots.

Enjoy the freedom of exploring San Gimignano at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Trevi Fountain. After exploring the monument, head to the iconic Pantheon. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Largo Di Torre Argentina, a place of eye-catching interest in San Gimignano.

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

Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

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

Day 8 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

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. You might also want to visit Monti, a neighborhood offering another perspective on the city.

Start your adventure at Vatican Museums. This wondrous art museum is a must-visit for travelers looking for a unique holiday experience. Make your way to St. Peter's Basilica located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Sistine Chapel. After the chapel, continue your tour of the city with a visit to Piazza Del Popolo. Visitors usually appreciate the visually striking features of this public square.

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.

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

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.

After enjoying a fulfilling meal, continue your evening at Sant' Eustachio Caffè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yellowsquare Rome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Naples. When you’re not sightseeing, take time to relax at your selected hotel in Naples, where you’ll be staying for 1 night.

Get ready to discover some of the most iconic wonders in Rome, including a castle, a museum, and a street. Start your day at Castel Sant'elmo. This culturally significant castle is a notable place to see in Rome. Then, wander over to Naples National Archaeological Museum. If noteworthy sites excite you, this museum will be right up your alley. Nearby, you’ll also find Cappella Sansevero. This photogenic museum 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, Spaccanapoli is an often recommended spot in the city that will captivate you with its unique charm.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Naples. Naples offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Naples. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at L'Oca Nera Irish Pub, a highly-rated dining destination in Naples. If you're eager to try something different, consider Mimì alla Ferrovia, another top spot with a tantalizing menu. You might also want to secure a reservation at Spuzzulè Winebar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Naples this evening.

Following your dinner, dive into the local bar culture at Happening Cocktail Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Shanti Art Musik Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Gran Caffè Gambrinus provides excellent drinks and a great atmosphere, ensuring 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.

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Pompei and Santa Maria degli Angeli. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rimini. You will spend 1 night here for some well-deserved relaxation.

Brace yourself for today’s incredible lineup of attractions in Naples, featuring fun adventures, scenic views, and picturesque spots. Start at Temple Of Venus, a worthwhile archeological site in the town. Then, head to Basilica and soak in the ambiance of this symbolic archeological site.

There are many interesting places to see in Naples, and when you are ready for more, go to Basilica Of San Francesco D'assisi. This is one of the town’s most notable stunning spots of interest. After exploring the church, visit the locally appreciated Portico Of Monte Frumentario.

When you’re done exploring for the day, you’ll drive to your hotel in Rimini. 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 Rimini. 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.

Treat yourself to a delicious dinner at Osteria Brodo di Giuggiole, an excellent option for tonight's dining. Looking for something different? Hotel Touring offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Lo Zodiaco Rimini. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rimini.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Hobo's, known for its inviting atmosphere. Sunflower City Backpacker is another great option if you’re looking for a place to get the night started. Similarly, Bar Capogiro 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!