14-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Florence, Siena, Rome, Naples, and Amalfi

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.

Today’s agenda in Bologna includes a botanical garden, a historical landmark, an art gallery, a church, a palace, a public square and much more! The Boboli Gardens is must-visit botanical garden and a great starting point for the day. Next, continue your journey to Ponte Vecchio, a wondrous historical landmark, located just a leisurely stroll away. Next, head to Uffizi Gallery, a historic art gallery, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bologna. When you're ready, let your sightseeing route take you to the interesting Basilica Of Santa Croce In Florence. If you’re looking for more, Palazzo Vecchio is also a notable attraction that is worthwhile a visit. Lastly, don’t miss Piazza Della Signoria, a place of romantic interest 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 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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazza Del Duomo, Pisa is the perfect place to start. This public square is one of the most timeless places to visit in Florence. Next, head to Pisa Cathedral, an often recommended church, known for its historic features.

Nearby, you'll also find Leaning Tower Of Pisa and Museo Dell'opera Del Duomo. Visit these for an interesting touch to your journey. Finish the day with a visit to Santa Maria Della Spina, an enchanting church in Florence.

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

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.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most locally appreciated attractions included on the itinerary is Basilica Of San Domenico. This breathtaking church will help you start your sightseeing on top. Then, take a leisurely stroll to Siena Cathedral and learn what makes this visually striking church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the up-and-coming Pubblico Palace. After exploring the palace, head to Piazza Del Campo. This widely recognized public square is a highlight in Florence. As your day continues, stop by Tower Of Mangia, known for its picture-perfect features.

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.

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

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

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.

Savor another day of unforgettable experiences in Italy!

On day 6 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience San Gimignano to the fullest today with this curated day itinerary!

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo. This curiosity-inducing public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Palazzo Comunale, Pinacoteca, Torre Grossa, one of the village’s best highlights.

Next, check out Sangimignano1300, one of the most frequently visited places to see in Siena. This museum is a favorite among locals and travelers alike.

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 2 nights.

Discover a day packed with fun adventures, breathtaking views, and picturesque spots in Siena. Begin your sightseeing with Colosseum. This globally renowned archeological site is one of the top attractions in the city. Proceed to Roman Forum, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Spanish Steps. This spectacular public square is a traveler-favorite. Not far away, you’ll find Piazza Di Spagna, another key site on your sightseeing itinerary. Trevi Fountain is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Rome 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 Vatican City and Rome.

A visit to Trastevere in Vatican City is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Vatican Museums.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to St. Peter's Basilica, a wondrous major basilica. For a change of scene, check out Pantheon, known for its monumental features. We also recommend visiting Piazza Navona. This public square is a must for anyone looking to experience the city to the fullest.

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

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

Enjoy a delicious meal 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.

Continue your evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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

On day 9 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 Naples. In the evening, you’ll end up in Naples, where you will stay for 2 nights.

Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Castel Sant'elmo. This popular 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 interesting 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 respected atmosphere this street offers.

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 explore more of Naples, 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.

Savor the flavors at L'Oca Nera Irish Pub, a top pick for dinner tonight. Alternatively, Mimì alla Ferrovia beckons with its unique menu offerings. Also, consider Spuzzulè Winebar. With its consistent customer satisfaction, it’s an excellent option for dining in Naples tonight.

Round off your dining experience by visiting Happening Cocktail Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Shanti Art Musik Bar, a bar catering to every mood and preference. Gran Caffè Gambrinus likewise offers a unique atmosphere, perfect for a memorable night out.

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

Wake up to day 10 of your extraordinary road trip in Italy. With 1 night left in Naples, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Enjoy the perfect balance of relaxation and exploration in Naples today. One of the most popular attractions included on the itinerary is Archaeological Park Of Pompeii. This picture-perfect archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Amphitheatre Of Pompeii and learn what makes this UNESCO world heritage-listed archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings.

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

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 lovely meal at Antica Pizzeria Di Matteo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Mercure Napoli Centro Angioino is another top choice with a popular menu. You could also check for a table at La Lazzara Trattoria e Pizzeria. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Naples tonight.

Round off your dining experience by visiting Archivio Storico - Cocktail Bar & Wonderfood, a prime location for a drink. Alternatively, explore the distinctive characteristics of Archeobar, a bar catering to every mood and preference. Babette Pub likewise offers a unique atmosphere, perfect for a memorable night out.

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

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 3 vibrant destinations - Positano, Vico Equense, and Nocelle. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Amalfi. You will spend 2 nights here for some well-deserved relaxation.

Naples is home to plenty of attractions that offer fun adventures, romantic experiences, and natural wonders! Start at Costiera Amalfitana Positano, a beloved beach that is worthwhile a visit in the village. Nearby, you’ll find Spiaggia Di Positano Marina Grande, enchanting visitors with its eye-catching appeal. Continue your exploration at Chiesa Di Santa Maria Assunta. This church is one of the village’s most frequently visited spots.

Enjoy the freedom of exploring Naples at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Viewpoint.8-amalfi Dr. After exploring the observation deck, head to the curiosity-inducing Vallone Porto.

At the end of the day, you will drive to Amalfi, 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 Amalfi's best restaurants.

Treat yourself to a delightful dinner at Pasticceria Pansa Amalfi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Grand Hotel Excelsior Amalfi? It's another excellent option with a diverse menu. Consider reserving a table at Lido Azzurro as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Amalfi.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Della Valle, a well-loved spot among locals and tourists.

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 Amalfi, where you'll stay for 1 night more.

Discover a day packed with fun adventures, photo-friendly spots, and historic treasures in Amalfi. Begin your sightseeing with Amalfi Coast. This extraordinary coast is one of the top attractions in the village. Proceed to Museo Della Carta, another must-visit attraction.

As you wander through the inviting streets of Amalfi, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Fondazione Ravello. This often recommended cultural center is a traveler-favorite. Not far away, you’ll find Villa Rufolo, another key site on your sightseeing itinerary. Villa Cimbrone Gardens is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Lungomare Di Maiori and uncover why it's recognized as one of the village's most locally appreciated attractions.

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

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

Enjoy a delicious meal at Ristorante Il Chiostro, a highly-rated dining destination in Amalfi. If you're eager to try something different, consider Gerry's pub, another top spot with a tantalizing menu. You might also want to secure a reservation at Pizzeria Donna Stella. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Amalfi this evening.

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

Dive into day 13 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli, 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 Bologna. You’ll stay here for 1 night.

Today’s route brings family-friendly attractions, breathtaking views, and photo-friendly spots. The first attraction of today is Portico Of Monte Frumentario. This worthwhile historical landmark is a culturally significant place to see in Amalfi. Continue your discovery at Basilica Of San Francesco D'assisi, a stunning church with stories to tell.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Amalfi.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Va Mo Là, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia. It’s yet another ideal choice to enhance your time in Bologna tonight.

Cap off your dinner by heading to Aurum, ideal for a leisurely evening with a drink in hand. Bar Senza Nome is another bar that offers an enjoyable setting. Similarly, Caffè Ristretto is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass to another unforgettable day in Italy!