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.

Get ready for a day filled with family-friendly attractions, romantic experiences, and natural wonders in the charming city of Rimini. Your adventure starts at Spiaggia Libera, a beloved local hot spot. Another notable attraction to explore is Parco Federico Fellini. This captivating park is known for its romantic appeal.

After soaking in the highlights of these sights, take some time to wander Rimini's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Domus Del Chirurgo. This respected archeological site offers a fascinating experience that many visitors find memorable. Parco Xxv Aprile is also worth visiting.

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.

Visit Rimini Factory Outlet in Rimini for an unforgettable shopping experience. Browse unique and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Rimini Factory Outlet has to offer, including attractions, essential services, and vibrant community activities.

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.

Enjoy a lovely dining experience at Osteria Brodo di Giuggiole, a popular restaurant in Rimini. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rimini at Hotel Touring, 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 Lo Zodiaco Rimini. It’s yet another ideal choice to enhance your time in Rimini tonight.

Following your dinner, dive into the local bar culture at Hobo's. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Sunflower City Backpacker, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Capogiro provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Savor another day of unforgettable experiences 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 Bologna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Today's adventure in Rimini promises more breathtaking discoveries and enriching experiences! Begin at Pinacoteca Nazionale Di Bologna. This visually striking art gallery is a highlight of any visit in the city. Then, enjoy Two Towers, another picture-perfect attraction that never fails to captivate visitors. Next, head over to Bologna Cathedral, one of the city’s most beloved attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Fountain Of Neptune, Bologna. This heritage-rich monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Portici Di Bologna, an increasingly popular street, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Maggiore before you head back to your hotel.

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.

Make sure to reserve a table at Ristorante Ciacco, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Ballarini, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sfoglia Rina, a hidden gem nestled in Bologna. 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 Bar Al Bricco D'oro, known for its inviting atmosphere. Bar Freud E Squisito is another great option if you’re looking for a place to get the night started. Similarly, Osteria Del Sole 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!

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. The Boboli Gardens is the first of them. Spend some time admiring this noteworthy botanical garden before continuing your journey. Ponte Vecchio is your next stop. This iconic historical landmark is one of the best-rated sights in Bologna.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Uffizi Gallery. This romantic art gallery is a sight to behold. To round off your sightseeing experience, visit Basilica Of Santa Croce In Florence and Palazzo Vecchio. If time allows, end your day with Piazza Della Signoria, a visually striking public square that offers a memorable conclusion to your exploration.

At the end of the day, you will drive to Florence, 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 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 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 enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

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

On day 5 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 1 night more, there’s no need to rush. Experience Pisa to the fullest today with this curated day itinerary!

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Florence. Your adventure starts at Santa Maria Della Spina, a locally appreciated local hot spot. Another notable attraction to explore is Knights' Square. This locally appreciated public square is known for its romantic appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This culturally significant monument offers a fascinating experience that many visitors find memorable. Pisa Cathedral is also worth visiting, along with Campo Santo. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Del Duomo, Pisa. This timeless public square provides a fitting finale to your sightseeing.

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

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

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Siena, 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 Siena. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, scenic views, and photo-friendly spots. Start at Fortezza Medicea (siena), a worthwhile monument in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this breathtaking church.

There are many interesting places to see in Florence, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most captivating inviting spots of interest. After exploring the church, visit the curiosity-inducing Pubblico Palace. Not far away, you'll also find Piazza Del Campo. This public square is a visually striking highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Tower Of Mangia, an underrated monument 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.

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.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Get a good night's sleep and look forward to another great day on the road 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 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 3 nights here for some well-deserved relaxation.

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Siena. Begin your sightseeing with Colosseum. This wondrous archeological site is one of the top attractions in the city. Proceed to Arch Of Constantine, 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 Roman Forum. This iconic archeological site is a traveler-favorite. Not far away, you’ll find Piazza Del Popolo, another key site on your sightseeing itinerary. Altare Della Patria 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.

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 lovely meal at La Bottega Roma, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Pasta In Corso is another top choice with a popular menu. You could also check for a table at Trattoria Vecchia Roma. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Almalu Trastevere is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Viminale Di Pepi Maurilio offers an excellent atmosphere for those looking to amp up the evening.

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

On day 8 of your road trip, you’ll start and end your day in Rome, where you'll stay for 2 nights more.

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

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Vatican Museums.

If you’re looking for more, spend time soaking in the atmosphere of Campo De' Fiori. This historic public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Navona, an iconic public square, and take a stroll around the area.

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.

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.

Round off your dining experience by visiting Sant' Eustachio Caffè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yellowsquare Rome, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s agenda in Rome includes a park, a public square, a monument, a castle and much more! Villa Borghese is must-visit park and a great starting point for the day. Next, continue your journey to Spanish Steps, a top-rated public square, located just a leisurely stroll away. Next, head to Piazza Di Spagna, a majestic public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the wondrous Trevi Fountain. If you’re looking for more, Pantheon is also an iconic attraction that is worthwhile a visit. Lastly, don’t miss Castel Sant'angelo, a place of enchanting interest in the city.

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 explore more of Rome, 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.

Enjoy a delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Cap off your dinner by heading to The Apartment Bar Roma, ideal for a leisurely evening with a drink in hand. Hotel Hassler Roma is another bar that offers an enjoyable setting.

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

On day 10 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 2 nights.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Castel Nuovo is the perfect place to start. This castle is one of the most notable places to visit in Rome. Next, head to Spaccanapoli, a locally appreciated street, known for its romantic 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 Cappella Sansevero. This heritage-rich museum is a highly recommended experience. Nearby, you'll also find Naples National Archaeological Museum and Piazza Del Plebiscito. Visit these for an interesting touch to your journey.

At the end of the day, you will drive to Naples, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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.

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

Keep the evening going at Happening Cocktail Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Shanti Art Musik Bar, which offers a similarly pleasant setting and great drinks. Another option is Gran Caffè Gambrinus, which provides an inviting environment for unwinding after a busy day out.

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

Greet day 11 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Naples 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 Pompei.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Naples allows for both. Start by heading to Archaeological Park Of Pompeii. This locally renowned archeological site provides an insightful glimpse into the town's identity. Next, discover Amphitheatre Of Pompeii, a picture-perfect archeological site, promising a delightful encounter.

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

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 Antica Pizzeria Di Matteo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mercure Napoli Centro Angioino? It's another excellent option with a diverse menu. Consider reserving a table at La Lazzara Trattoria e Pizzeria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Naples.

Continue your lively evening at Archivio Storico - Cocktail Bar & Wonderfood, a perfect place for winding down or revving up the night, depending on which mood you’re in. Archeobar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Babette Pub ensures a night out tailored to your taste.

Raise your glass to another unforgettable day in Italy!

On day 12 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 Santa Maria degli Angeli. In the evening, you’ll end up in Santa Maria degli Angeli, where you will stay for 1 night.

Naples is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Basilica Of Santa Maria Degli Angeli, a popular church that is worthwhile a visit in the village. Nearby, you’ll find Basilica Of San Francesco D'assisi, enchanting visitors with its UNESCO world heritage-designated appeal. Continue your exploration at Rocca Maggiore. This castle is one of the village’s most intriguing 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 Piazza Del Comune.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Santa Maria degli Angeli. Santa Maria degli Angeli 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 Santa Maria degli Angeli's best restaurants.

If you’re not ready to end the night just yet, Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings offers a perfect venue to relax and savor a drink.

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.

Embark on another extraordinary experience on day 13 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of City of San Marino. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rimini, which will be your home away from home for 1 night.

The first attraction of today is State Museum Of San Marino.

As you stroll around Santa Maria degli Angeli, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Basilica Del Santo. Next, make your way to Guaita Tower to add another highlight to your day. After that, visit Monte Titano, a curiosity-inducing mountain that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Montale, an increasingly popular mountain 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 Santa Maria degli Angeli.

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 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.

Treat yourself to a delicious dinner at Amarina, an excellent option for tonight's dining. Looking for something different? Primo Miglio di Conti Mirco offers a tantalizing alternative with its diverse menu. And don’t miss Libeccio. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rimini.

After savoring a delicious meal, step into the vibrant nightlife at Caffè Cavour, where the evening is just getting started. In the same way, Bar Ilde - Il Baretto Della Buona Piadina offers a unique charm perfect for experiencing the local bar scene in Rimini. Bar Malatesta is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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