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

Day 2 offers a multitude of experiences. You will stay in Rimini for 1 night more, offering you enough time to explore at a relaxed pace.

Brace yourself for today’s incredible lineup of attractions in Rimini, featuring family-friendly attractions, romantic experiences, and natural wonders. Start at Spiaggia Libera, an up-and-coming beach in the city. Then, head to Parco Federico Fellini and soak in the ambiance of this romantic park.

There are many interesting places to see in Rimini, and when you are ready for more, go to Domus Del Chirurgo. This is one of the city’s most beloved standout spots of interest. After exploring the archeological site, visit the intriguing Parco Xxv Aprile.

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.

Experience shopping bliss at Rimini as you explore Rimini Factory Outlet. Take a leisurely stroll through unique and shops, where local treasures are waiting to be found. Beyond shopping, Rimini Factory Outlet offers more options, including unique attractions, key services, and vibrant events.

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 wonderful meal at Osteria Brodo di Giuggiole, a top-rated dining spot in Rimini. If you're in the mood for something new, try Hotel Touring, another premier location with a delectable menu. You might also want to book a table at Ristorante Lo Zodiaco Rimini. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rimini.

After your meal, keep the night alive at a bar like Hobo's, known for its lively atmosphere. Sunflower City Backpacker is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Capogiro offers an excellent atmosphere for those looking to amp up the evening.

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

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

If you’re looking for more, spend time soaking in the atmosphere of Fountain Of Neptune, Bologna. This symbolic monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Portici Di Bologna, an often recommended 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.

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

Enjoy a lovely dining experience at Ristorante Ciacco, 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 Ristorante Ballarini, 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 Sfoglia Rina. It’s yet another ideal choice to enhance your time in Bologna tonight.

Following your dinner, dive into the local bar culture at Bar Al Bricco D'oro. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Freud E Squisito, the perfect place for those looking to experience the best of the nightlife. Similarly, Osteria Del Sole provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to The Boboli Gardens. This well-known botanical garden provides an insightful glimpse into the city's identity. Next, discover Ponte Vecchio, a history-steeped historical landmark, promising a delightful encounter.

Continue your sightseeing with a visit to Uffizi Gallery, a top-rated art gallery. When you’re done, don’t forget to make a stop at the interesting Basilica Of Santa Croce In Florence. Not far away from the church, you will find the masterful Piazza Della Signoria, perfect for a quick visit. Round off your day at Palazzo Vecchio, another gem in Bologna with romantic features to discover.

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.

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.

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.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Start by visiting Santa Maria Della Spina, a prime spot to begin your journey. This enchanting church is sure to impress. Next on your list is Knights' Square, another must-visit landmark and curiosity-inducing public square renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Leaning Tower Of Pisa. This UNESCO world heritage-designated monument is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Pisa Cathedral, an intriguing church. Nearby, you'll also find Campo Santo, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazza Del Duomo, Pisa and wrap up your day with its stunning appeal.

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

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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day 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.

Today, you'll explore some of the most beautiful places in Florence, including a monument, a church, a palace, a public square and much more! Start your day with a visit to Fortezza Medicea (siena). This up-and-coming monument is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of San Domenico, which may be one of the most stunning places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Siena Cathedral, a well-known church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pubblico Palace and Piazza Del Campo. End your day with a visit to Tower Of Mangia, an intriguing monument that’s sure to leave a lasting impression.

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.

As you explore more of Siena, 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.

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.

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

On day 7 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 Rome. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Today’s agenda in Siena includes an archeological site, a monument, and a public square. Colosseum is must-visit archeological site and a great starting point for the day. Next, continue your journey to Arch Of Constantine, an often recommended monument, located just a leisurely stroll away. Next, head to Roman Forum, a breathtaking archeological site, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the astonishing Piazza Del Popolo. If you’re looking for more, Altare Della Patria is also a popular attraction that is worthwhile a visit.

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 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.

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Round off your dining experience by visiting La Botticella Of Poggi Giovanni, a prime location for a drink. Alternatively, explore the distinctive characteristics of Almalu Trastevere, a bar catering to every mood and preference. Bar Viminale Di Pepi Maurilio likewise offers a unique atmosphere, perfect for a memorable night out.

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 8 of your road trip in Italy, you’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 2 nights more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

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.

Start your adventure at Vatican Museums. This timeless art museum is a place that is appreciated by travelers and locals alike.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to St. Peter's Basilica. This timeless major basilica offers an enriching experience. For a change of pace, head to Campo De' Fiori, where you can take in picture-perfect features. Conclude your self-guided sightseeing tour with a visit to Piazza Navona. These sights offer a fulfilling end to a perfect day.

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.

Treat yourself to a delightful dinner at RomAntica, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Coso Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at DEROMA - Farine Romane as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

To truly maximize your evening out, consider visiting Sant' Eustachio Caffè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yellowsquare Rome, another bar with an inviting ambiance. Similarly, Caffè Portofino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Savor another day of unforgettable experiences in Italy!

On day 9 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Set out on a day brimming with fun adventures, romantic experiences, and natural wonders. Start at the extraordinary Villa Borghese, a mesmerizing park in Rome. Next, go to Spanish Steps.

After visiting Villa Borghese and Spanish Steps, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Piazza Di Spagna. This enchanting 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 photogenic places to visit in Rome. If you still have some time left for sightseeing, we also recommend stopping by Castel Sant'angelo.

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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Naples, 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 Naples. You’ll stay here for 2 nights.

Today’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Castel Nuovo. This popular castle is a picture-perfect place to see in Rome. Continue your discovery at Spaccanapoli, a romantic street with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Cappella Sansevero. This captivating museum offers a detailed encounter with Rome. Next, make your way to Naples National Archaeological Museum to add another highlight to your day. After that, visit Piazza Del Plebiscito, an extraordinary public square that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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 dinnertime approaches, it's time to head out for a bite to eat in Naples. 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 L'Oca Nera Irish Pub, an iconic dining spot in Naples. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Mimì alla Ferrovia, a popular restaurant in Naples. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Spuzzulè Winebar, a hidden gem nestled in Naples. 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. Happening Cocktail Bar is an excellent place to start. You could also check out Shanti Art Musik Bar, offering a different kind of charm. A last recommendation for the day is Gran Caffè Gambrinus. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and recharge in preparation for another adventurous day 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.

Bring your curiosity for today’s adventure around Naples. Some of the town’s most loved attractions await! Archaeological Park Of Pompeii is the perfect place to start. This archeological site is one of the most notable places to visit in Naples. Next, head to Amphitheatre Of Pompeii, a popular archeological site, known for its picture-perfect features.

Visit these for an interesting touch to your journey.

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 dining experience at Antica Pizzeria Di Matteo, a popular restaurant in Naples. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Naples at Mercure Napoli Centro Angioino, 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 La Lazzara Trattoria e Pizzeria. It’s yet another ideal choice to enhance your time in Naples tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Archivio Storico - Cocktail Bar & Wonderfood stands out as an excellent choice for a post-dinner cocktail. Alternatively, Archeobar offers an ideal atmosphere to enjoy the pleasures of the night. Babette Pub is also a great option that provides a perfect setting for a relaxing 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.

Embark on another extraordinary experience on day 12 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Santa Maria degli Angeli. At the end of the day, you will enjoy the comforts of a top-rated hotel in Santa Maria degli Angeli, which will be your home away from home for 1 night.

Naples is brimming with adventures. Today’s wonderful stops include a church, a castle, and a public square. Begin your sightseeing adventure at the popular Basilica Of Santa Maria Degli Angeli and allow yourself time to explore. Just a short distance away you'll find your next stop, Basilica Of San Francesco D'assisi, a picture-perfect church that draws visitors from far and near.

Continue your journey to Rocca Maggiore, one of the village’s most locally appreciated spots that you shouldn’t miss. Another great site to visit is the increasingly popular 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.

After savoring a delicious meal, step into the vibrant nightlife at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, where the evening is just getting started.

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

Experience an unparalleled adventure on day 13 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - City of San Marino. 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.

Start your adventure at State Museum Of San Marino. This frequently visited museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Liberty Square located in Santa Maria degli Angeli for another exciting encounter.

Next, immerse yourself in the setting of Basilica Del Santo. After the church, continue your tour of the city with a visit to Guaita Tower. Next up is Monte Titano, a highly recommended mountain. For a change of pace, head to Montale. As one of the most curiosity-inducing attractions in Santa Maria degli Angeli, this mountain is the perfect place to end your self-guided sightseeing tour.

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.

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

Treat yourself to a wonderful meal at Amarina, a top-rated dining spot in Rimini. If you're in the mood for something new, try Primo Miglio di Conti Mirco, another premier location with a delectable menu. You might also want to book a table at Libeccio. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rimini.

Continue your evening by exploring the vibrant nightlife scene at Caffè Cavour, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Ilde - Il Baretto Della Buona Piadina, a bar that offers unique local touches. Likewise, Bar Malatesta 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.