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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rimini allows for both. Start by heading to Spiaggia Libera. This up-and-coming beach provides an insightful glimpse into the city's identity. Next, discover Parco Federico Fellini, a romantic park, promising a delightful encounter.

Continue your sightseeing with a visit to Domus Del Chirurgo, a beloved archeological site. When you’re done, don’t forget to make a stop at the often recommended 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 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 Osteria Brodo di Giuggiole, an excellent option for tonight's dining. Looking for something different? Hotel Touring offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Lo Zodiaco Rimini. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rimini.

If you’re not ready to end the night just yet, Hobo's offers a perfect venue to relax and savor a drink. Similarly, Sunflower City Backpacker is well-suited for those looking to unwind in a social setting. Bar Capogiro is another excellent spot to enjoy a nightcap after a delightful meal.

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.

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.

Today’s agenda in Rimini includes an art gallery, a monument, a church, a street, a public square and much more! Pinacoteca Nazionale Di Bologna is must-visit art gallery and a great starting point for the day. Next, continue your journey to Two Towers, a popular monument, located just a leisurely stroll away. Next, head to Bologna Cathedral, a picture-perfect church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rimini. If you’re looking for more, Fountain Of Neptune, Bologna is also a frequently visited attraction that is worthwhile a visit. Lastly, don’t miss Portici Di Bologna, a frequently visited gem to see in the city.

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 explore more of Bologna, 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 delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Keep the excitement of the evening going by visiting a bar or two. Bar Al Bricco D'oro is an excellent place to start. You could also check out Bar Freud E Squisito, offering a different kind of charm. A last recommendation for the day is Osteria Del Sole. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying 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 an interesting place to see in Bologna. Then, wander over to Ponte Vecchio. If enchanting sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This instagrammable 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 an interesting 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 romantic Palazzo Vecchio. Take a moment to appreciate the fascinating details of this interesting palace in Bologna.

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

Enjoy a delicious meal 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.

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.

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.

Today’s agenda in Florence includes a church, a public square, a monument, a cemetery and much more! Santa Maria Della Spina is must-visit church and a great starting point for the day. Next, continue your journey to Knights' Square, an increasingly popular public square, located just a leisurely stroll away. Next, head to Leaning Tower Of Pisa, a culturally significant monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. If you’re looking for more, Pisa Cathedral is also a curiosity-inducing attraction that is worthwhile a visit. Lastly, don’t miss Campo Santo, an underrated gem to see in the city.

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

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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the intriguing Fortezza Medicea (siena), a culturally significant monument in Florence. Next, go to Basilica Of San Domenico.

After visiting Fortezza Medicea (siena) and Basilica Of San Domenico, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Siena Cathedral. This visually striking church offers a unique experience. Pubblico Palace is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Piazza Del Campo, one of the most enchanting places to visit in Florence.

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.

Enjoy a lovely dining experience at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

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.

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.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Colosseum. This world-famous archeological site is a breathtaking place to see in Siena. Continue your discovery at Arch Of Constantine, a breathtaking monument with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Roman Forum. This wondrous archeological site offers a culturally significant encounter with Siena. Next, make your way to Piazza Del Popolo to add another highlight to your day. After that, visit Altare Della Patria, an interesting monument 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 Siena.

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.

Don’t miss out on dining at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

Get a good night's sleep and look forward to another great day on the road 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 2 nights 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.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Start your adventure at Vatican Museums. This iconic art museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Sistine Chapel located in Rome for an enchanting atmosphere.

Next, immerse yourself in the setting of St. Peter's Basilica. After the major basilica, continue your tour of the city with a visit to Campo De' Fiori. This public square has a historic appeal. For a change of pace, head to Piazza Navona. As one of the most wondrous attractions in Rome, this public square is an excellent place to end your self-guided tour.

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

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

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Sant' Eustachio Caffè, known for its inviting atmosphere. Yellowsquare Rome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

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

Rome is home to plenty of attractions that offer fun adventures, romantic experiences, and natural wonders! Start at Villa Borghese, an impressive park that is worthwhile a visit in the city. Nearby, you’ll find Spanish Steps, enchanting visitors with its symbolic appeal. Continue your exploration at Piazza Di Spagna. This public square is one of the city’s most wondrous spots.

Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Trevi Fountain. After exploring the monument, head to the timeless Pantheon. This monument will wrap up today’s self-guided sightseeing tour 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.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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.

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

On day 10 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.

A blend of family-friendly attractions, scenic views, and photo-friendly spots await you in Rome on today’s itinerary. First up is the captivating castle, Castel Nuovo. Afterward, continue to Spaccanapoli, a street every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Cappella Sansevero. This popular museum is an essential stop. Following that, head to Naples National Archaeological Museum, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Plebiscito, an extraordinary public square in the city.

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.

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

Unwind after your meal by stepping into Happening Cocktail Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Shanti Art Musik Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Gran Caffè Gambrinus, another top-rated bar in the area.

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

On day 11 of your road trip in Italy, you’ll start and end your day in Naples, but spend the day exploring what’s beyond the city. Since you will return to Naples for 1 night more, there’s no need to rush. Experience Pompei to the fullest today with this curated day itinerary!

Brace yourself for today’s incredible lineup of attractions in Naples, featuring fun adventures, scenic views, and picturesque spots. Start at Archaeological Park Of Pompeii, an interesting archeological site in the town. Then, head to Amphitheatre Of Pompeii and soak in the ambiance of this historic archeological site.

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

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.

Make sure to reserve a table at Antica Pizzeria Di Matteo, 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 Mercure Napoli Centro Angioino, 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 La Lazzara Trattoria e Pizzeria, a hidden gem nestled in Naples. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Archivio Storico - Cocktail Bar & Wonderfood, a prime destination for a thrilling night out. Also, don’t forget to check out Archeobar, a bar that offers unique local touches. Likewise, Babette Pub provides an excellent alternative for a fun evening.

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 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.

Prepare for a day full of fun adventures, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Basilica Of Santa Maria Degli Angeli. This interesting church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of San Francesco D'assisi, one of the village’s best highlights.

Next, check out Rocca Maggiore, one of the most worthwhile places to see in Naples. This castle is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Comune. Wander around and soak in the visually striking atmosphere this public square offers.

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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Santa Maria degli Angeli. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings stands out as an excellent choice for a post-dinner cocktail.

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.

On day 13 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, City of San Marino. When you’re not sightseeing, take time to relax at your selected hotel in Rimini, where you’ll be staying for 1 night.

Enjoy the perfect balance of relaxation and exploration in Santa Maria degli Angeli today. One of the most frequently visited attractions included on the itinerary is State Museum Of San Marino.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the frequently visited Basilica Del Santo. After exploring the church, head to Guaita Tower. This interesting point of interest is a highlight in Santa Maria degli Angeli. Lastly, don’t forget to check out the often recommended Monte Titano. Enjoy exploring this incredible mountain at your own pace.

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 explore more of Rimini, 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.

Make sure to reserve a table at Amarina, 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 Primo Miglio di Conti Mirco, 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 Libeccio, a hidden gem nestled in Rimini. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Caffè Cavour, ideal for a leisurely evening with a drink in hand. Bar Ilde - Il Baretto Della Buona Piadina is another bar that offers an enjoyable setting. Similarly, Bar Malatesta is also a popular place to go on a night out, perfect for relaxing and socializing.

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