14-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling south to Bologna, Florence, Siena, Rome, Naples, and Santa Maria degli Angeli

On day 2 of your road trip, you will have an entire day to explore Rimini. You’ll stay in Rimini for 1 night and discover all the best things to see and do in the area.

Today's adventure in Rimini promises more breathtaking discoveries and enriching experiences! Begin at Spiaggia Libera. This serene beach is a highlight of any visit in the city. Then, enjoy Parco Federico Fellini, another romantic attraction that never fails to captivate visitors. Next, head over to Domus Del Chirurgo, one of the city’s most underrated attractions, known for its respected features.

If you’re looking for more, spend time soaking in the atmosphere of Parco Xxv Aprile. This majestic park is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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 shopping spree at Rimini's top shopping destination, Rimini Centro! Enjoy the freedom to explore at your own pace, browsing unique boutique shops and discovering local treasures. Keep an eye out for artisan crafts, perfect for bringing a touch of Italy into your home. Beyond shopping, Rimini Centro has plenty to offer, including essential services, seasonal events, and unique attractions for all ages.

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

Make sure to reserve a table at Osteria Brodo di Giuggiole, an iconic dining spot in Rimini. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Hotel Touring, a popular restaurant in Rimini. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Lo Zodiaco Rimini, a hidden gem nestled in Rimini. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - 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 often recommended attractions included on the itinerary is Pinacoteca Nazionale Di Bologna. This visually striking art gallery will help you start your sightseeing on top. Then, take a leisurely stroll to Two Towers and learn what makes this picture-perfect monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the underrated Bologna Cathedral. After exploring the church, head to Fountain Of Neptune, Bologna. This frequently visited monument is a highlight in Rimini. As your day continues, stop by Portici Di Bologna, known for its romantic features. Lastly, don’t forget to check out the famous Piazza Maggiore. Enjoy exploring this incredible public square at your own pace.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna 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 Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely meal at Ristorante Ciacco, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Ballarini is another top choice with a popular menu. You could also check for a table at Sfoglia Rina. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

Explore the vibrant nightlife at Bar Al Bricco D'oro after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Freud E Squisito for a great selection of flavorful drinks and a charming setting. Furthermore, Osteria Del Sole is perfect for those looking to extend their night with a touch of local flavor.

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 4 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.

Get ready to discover some of the most iconic wonders in Bologna, including a botanical garden, a historical landmark, an art gallery, a church, a palace, a public square and much more! Start your day at The Boboli Gardens. This visually striking botanical garden is a locally renowned place to see in Bologna. Then, wander over to Ponte Vecchio. If visually striking sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This historic art gallery is a favorite among visitors.

Bologna offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Basilica Of Santa Croce In Florence is a well-known spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the enchanting Palazzo Vecchio. Take a moment to appreciate the fascinating details of this popular palace. Wrap up your self-guided tour of Bologna's top attractions with a visit to Piazza Della Signoria.

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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.

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

Wake up to day 5 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!

Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Santa Maria Della Spina. This curiosity-inducing church is an inviting place to see in Florence. Continue your discovery at Knights' Square, a culturally significant public square with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Leaning Tower Of Pisa. This iconic monument offers a detailed encounter with Florence. Next, make your way to Pisa Cathedral to add another highlight to your day. After that, visit Campo Santo, a worthwhile cemetery that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Del Duomo, Pisa, a wondrous public square in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in 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.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 6 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 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a church, a palace, a public square and much more! Begin your adventure at Fortezza Medicea (siena). This is an up-and-coming monument you should not miss. Another must-see is Basilica Of San Domenico, a worthwhile church in Florence.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Pubblico Palace, another of the city’s curiosity-inducing attractions. We recommend continuing your self-guided tour at Piazza Del Campo, a romantic place of interest in the city. If time allows, add Tower Of Mangia to your itinerary. This increasingly popular monument offers the perfect finishing touch to your day in Florence.

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.

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.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip 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 3 nights.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Colosseum is the perfect place to start. This archeological site is one of the most timeless places to visit in Siena. Next, head to Arch Of Constantine, an often recommended monument, known for its historic 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 Roman Forum. This historic archeological site is a highly recommended experience. Nearby, you'll also find Piazza Del Popolo and Altare Della Patria. Visit these for an interesting touch to your journey.

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.

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

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.

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

At the end of the day, you'll drive back to Rome, where you'll stay for 2 nights more.

Trastevere is one of the highlights of today. Take your time exploring this iconic neighborhood in Vatican City, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Start your day at Vatican Museums. Then, wander over to Sistine Chapel. Nearby, you’ll also find St. Peter's Basilica.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Campo De' Fiori is an astonishing spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the enchanting Piazza Navona. Take a moment to appreciate the fascinating details of this globally renowned public square.

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

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 RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent 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.

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.

Day 9 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Discover a day packed with family-friendly attractions, romantic experiences, and natural wonders in Rome. Begin your sightseeing with Villa Borghese. This famous park is one of the top attractions in the city. Proceed to Spanish Steps, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Di Spagna. This iconic public square is a traveler-favorite. Not far away, you’ll find Trevi Fountain, another key site on your sightseeing itinerary. Pantheon is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Castel Sant'angelo and uncover why it's recognized as one of the city's most extraordinary attractions.

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.

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.

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

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

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Naples. At the end of the day, you will enjoy the comforts of a top-rated hotel in Naples, which will be your home away from home for 2 nights.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Castel Nuovo. This picture-perfect castle is a highlight of any visit in the city. Then, enjoy Spaccanapoli, another enchanting attraction that never fails to captivate visitors. Next, head over to Cappella Sansevero, one of the city’s most interesting attractions, known for its respected features.

If you’re looking for more, spend time soaking in the atmosphere of Naples National Archaeological Museum. This heritage-rich museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Plebiscito, an astonishing public square, and take a stroll around the area.

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

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Naples. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at L'Oca Nera Irish Pub, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mimì alla Ferrovia? It's another excellent option with a diverse menu. Consider reserving a table at Spuzzulè Winebar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Naples.

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

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

On day 11 of your road trip, you’ll start and end your day in Naples, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pompei. You still have 1 night left in Naples.

Just a short distance away you'll find your next stop, Amphitheatre Of Pompeii, a picture-perfect archeological site that draws visitors from far and near.

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.

Treat yourself to a delicious dinner at Antica Pizzeria Di Matteo, an excellent option for tonight's dining. Looking for something different? Mercure Napoli Centro Angioino offers a tantalizing alternative with its diverse menu. And don’t miss La Lazzara Trattoria e Pizzeria. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Naples.

To truly maximize your evening out, consider visiting Archivio Storico - Cocktail Bar & Wonderfood after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Archeobar, another bar with an inviting ambiance. Similarly, Babette Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Experience an unparalleled adventure on day 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Santa Maria degli Angeli. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Santa Maria degli Angeli. You will spend 1 night here for some well-deserved relaxation.

Brace yourself for today’s incredible lineup of attractions in Naples, featuring family-friendly attractions, scenic views, and picturesque spots. Start at Basilica Of Santa Maria Degli Angeli, a captivating church in the village. Then, head to Basilica Of San Francesco D'assisi and soak in the ambiance of this breathtaking church.

There are many interesting places to see in Naples, and when you are ready for more, go to Rocca Maggiore. This is one of the village’s most locally appreciated romantic spots of interest. After exploring the castle, visit the increasingly popular Piazza Del Comune.

At the end of the day, you will drive to Santa Maria degli Angeli, 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 Santa Maria degli Angeli. If you are looking to dine at a popular restaurant in the town, it's often a good idea to reserve a table in advance.

Continue your evening by exploring the vibrant nightlife scene at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a prime destination for a thrilling night out.

Savor another day of unforgettable experiences in Italy!

On day 13 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 City of San Marino. In the evening, you’ll end up in Rimini, where you will stay for 1 night.

First up is the frequently visited museum, State Museum Of San Marino. Afterward, continue to Liberty Square, a sightseeing destination every traveler should visit.

As you explore Santa Maria degli Angeli’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Basilica Del Santo. This increasingly popular church is an essential stop. Following that, head to Guaita Tower, another must-visit site that will enhance your experience. Don’t forget to stop by Monte Titano, a curiosity-inducing mountain 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 Rimini. Rimini 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 Rimini. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Have a fantastic dining experience at Amarina, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Primo Miglio di Conti Mirco offers an enticing alternative with its varied menu. Additionally, Libeccio is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rimini.

Continue the enjoyment post-dinner at Caffè Cavour, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Ilde - Il Baretto Della Buona Piadina offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Malatesta. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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