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

Dive into day 2 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Rimini and Bologna. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna, where you'll spend 1 night.

Check out the well-known monument, Arch Of Augustus. Afterward, continue to Piazza Santo Stefano, a public square every traveler should visit. As you explore Rimini’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Two Towers. This notable monument is an essential stop. Following that, head to Bologna Cathedral, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Maggiore, a famous public square in the city.

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.

Bologna is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Bologna.

Dine in style at Ristorante Ciacco, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Ballarini boasts a menu that's sure to impress. Also, be sure to check out Sfoglia Rina. Known as a local hotspot, it’s a great choice for tonight in Bologna.

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day in Italy!

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

Catch The Boboli Gardens before the crowds roll in. This history-steeped botanical garden is sure to ignite your curiosity. Next, dive into the visually striking features of Ponte Vecchio, a must-visit historical landmark in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Uffizi Gallery, a widely recognized art gallery. For a change of scene, check out Basilica Of Santa Croce In Florence, known for its instagrammable features. We also recommend visiting Palazzo Vecchio. This palace is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazza Della Signoria, yet another widely recognized attraction in Bologna.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax 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.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. Known for great service, it’s a fantastic choice 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.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Wake up to day 4 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Pisa is brimming with adventures.

Leaning Tower Of Pisa is must-visit monument and a great option for a daytime tour of the area. Continue your journey to Angelo Caduto, an often recommended sightseeing destination, located just a leisurely stroll away. Next, head to Pisa Cathedral, a breathtaking church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the increasingly popular Campo Santo. If you’re looking for more, Piazza Del Duomo, Pisa is also a globally renowned attraction that is worthwhile a visit.

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

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

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Siena and San Gimignano. When you’re not sightseeing, take time to relax at your chosen hotel in San Gimignano, where you’ll be staying for 2 nights.

Experience Siena Cathedral, a well-known church in the city. Then, head to Piazza Del Campo and soak in the ambiance of this enchanting public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Tower Of Mangia. This is one of the city’s most curiosity-inducing culturally significant spots of interest. After exploring the monument, visit the curiosity-inducing Sangimignano1300. Not far away, you'll also find Piazza Del Duomo. This public square is a history-steeped highlight in Florence.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in San Gimignano. San Gimignano 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 San Gimignano's best restaurants.

Savor another day of unforgettable experiences in Italy!

On day 6 of your road trip, you’ll start and end your day in San Gimignano, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate village, including San Regolo and Castellina in Chianti.

Castello Di Brolio is perfect for a self-paced visit during the day. This romantic castle is sure to impress. Next on your list is Tumulo Di Montecalvario, another must-visit landmark and increasingly popular archeological site renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of San Gimignano by sampling some local delicacies. When you’re ready for more sightseeing, head to Rocca Di Castellina In Chianti. This romantic castle is an essential place to visit for anyone looking for the full San Gimignano experience.

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

San Gimignano is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in San Gimignano.

Savor another day of unforgettable experiences 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 1 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 2 nights.

Awaiting your discovery is the top-rated Castel Sant'angelo, an enchanting castle in San Gimignano. Next, go to Piazza Navona.

After visiting Castel Sant'angelo and Piazza Navona, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Spanish Steps. This romantic public square offers a unique experience. Trevi Fountain is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Pantheon, one of the most culturally significant places to visit in San Gimignano. If you still have some time left for sightseeing, we also recommend stopping by Largo Di Torre Argentina.

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 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.

Savor the flavors at La Bottega Roma, a top pick for dinner tonight. Alternatively, Pasta In Corso beckons with its unique menu offerings. Also, consider Trattoria Vecchia Roma. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Let the evening flow smoothly from dinner to drinks at La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Almalu Trastevere provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Viminale Di Pepi Maurilio offers a memorable night with diverse drink options and excellent service.

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

Day 8 of your road trip will take you to the best attractions Vatican City has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Vatican City.

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights. You should also check out Monti, a neighborhood offering more opportunities to enjoy the city’s vibrant atmosphere and landmarks.

Whatever your travel style is, Vatican Museums is an essential stop in Rome. This wondrous art museum provides an insightful glimpse into the city's identity.

Continue your sightseeing with a visit to Sistine Chapel, a top-rated chapel. When you’re done, don’t forget to make a stop at the spectacular Piazza Del Popolo.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Treat yourself to a delicious dinner at RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. Known for great service, it’s a fantastic choice for tonight in Rome.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day in Italy!

On day 9 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Naples are on today's agenda. In the evening, you’ll end up in Naples, where you will stay for 1 night.

To truly experience Rome, make sure to drop by Castel Sant'elmo. This notable castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Naples National Archaeological Museum, one of the city’s best highlights.

Next, check out Cappella Sansevero, one of the most notable places to see in Rome. This museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Spaccanapoli. Wander around and soak in the enchanting atmosphere this street offers.

When you’re done exploring for the day, you’ll drive to your hotel in Naples. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Naples's most popular restaurants, and connect with friendly locals for a true cultural experience.

Treat yourself to a wonderful meal at L'Oca Nera Irish Pub, a top-rated dining spot in Naples. If you're in the mood for something new, try Mimì alla Ferrovia, another premier location with a delectable menu. You might also want to book a table at Spuzzulè Winebar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Naples.

Cap off your dinner by heading to Happening Cocktail Bar, ideal for a leisurely evening with a drink in hand. Shanti Art Musik Bar is another bar that offers an enjoyable setting. Similarly, Gran Caffè Gambrinus is also a popular place to go on a night out, perfect for relaxing and socializing.

Head back to your accommodation in Naples and get some rest to prepare for another magical day of your road trip in Italy.

Dive into day 10 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Pompei and Santa Maria degli Angeli. At the end of the day, you’ll unwind at one of the finest accommodations in Rimini, where you'll spend 1 night.

Temple Of Venus is must-visit archeological site and a great option for a daytime tour of the area. Continue your journey to Basilica, a curiosity-inducing archeological site, located just a leisurely stroll away. Next, head to Basilica Of San Francesco D'assisi, a majestic church, also available for your discovery today.

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

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

Treat yourself to a delightful dinner at Osteria Brodo di Giuggiole, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Hotel Touring? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Lo Zodiaco Rimini as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rimini.

To truly maximize your evening out, consider visiting Hobo's after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Sunflower City Backpacker, another bar with an inviting ambiance. Similarly, Bar Capogiro also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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