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

Today’s agenda in Rimini includes a beach, a park, and an archeological site. Spiaggia Libera is must-visit beach and a great starting point for the day. Next, continue your journey to Parco Federico Fellini, a popular park, located just a leisurely stroll away. Next, head to Domus Del Chirurgo, a heritage-rich archeological site, also available for your discovery today.

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.

Elevate your experience in Rimini with a visit to the city's premier shopping location, Rimini Centro. Explore unique boutique shops and uncover hidden gems along the way. For a cultural touch, look for artisan crafts that perfectly capture the charm of Italy. After shopping, enjoy nearby attractions or simply people-watch and capture memorable photos.

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

Enjoy a lovely meal at Osteria Brodo di Giuggiole, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Hotel Touring is another top choice with a popular menu. You could also check for a table at Ristorante Lo Zodiaco Rimini. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rimini tonight.

Cap off your dinner by heading to Hobo's, ideal for a leisurely evening with a drink in hand. Sunflower City Backpacker is another bar that offers an enjoyable setting. Similarly, Bar Capogiro is also a popular place to go on a night out, perfect for relaxing and socializing.

Say good night to Rimini and look forward to another great day of your road trip 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.

Brace yourself for today’s incredible lineup of attractions in Rimini, featuring family-friendly attractions, photo-friendly spots, and historic treasures. Start at Pinacoteca Nazionale Di Bologna, a worthwhile art gallery in the city. Then, head to Two Towers and soak in the ambiance of this standout monument.

There are many interesting places to see in Rimini, and when you are ready for more, go to Bologna Cathedral. This is one of the city’s most underrated respected spots of interest. After exploring the church, visit the intriguing Fountain Of Neptune, Bologna. Not far away, you'll also find Portici Di Bologna. This street is a respected highlight in Rimini. Before wrapping up your self-guided sightseeing tour, head to Piazza Maggiore, a spectacular public square in the city.

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

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

Treat yourself to a wonderful meal at Ristorante Ciacco, a top-rated dining spot in Bologna. If you're in the mood for something new, try Ristorante Ballarini, another premier location with a delectable menu. You might also want to book a table at Sfoglia Rina. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

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.

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 2 nights.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the interesting The Boboli Gardens, a visually striking botanical garden in Bologna. Next, go to Ponte Vecchio.

After visiting The Boboli Gardens and Ponte Vecchio, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Uffizi Gallery. This eye-catching art gallery offers a unique experience. Basilica Of Santa Croce In Florence is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Palazzo Vecchio, one of the most majestic places to visit in Bologna. If you still have some time left for sightseeing, we also recommend stopping by Piazza Della Signoria.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Say good night to Florence and look forward to another great day of your road trip in Italy!

On day 5 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pisa. You still have 1 night left in Florence.

Start by visiting Santa Maria Della Spina, a prime spot to begin your journey. This romantic church is sure to impress. Next on your list is Knights' Square, another must-visit landmark and locally appreciated public square renowned for its breathtaking 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-listed monument is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Pisa Cathedral, an underrated 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 for the day, you’ll return to Florence and your accommodation.

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.

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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.

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.

Florence is brimming with adventures. Today’s wonderful stops include a monument, a church, a palace, a public square and much more! Begin your sightseeing adventure at the worthwhile Fortezza Medicea (siena) and allow yourself time to explore. Just a short distance away you'll find your next stop, Basilica Of San Domenico, a picture-perfect church that draws visitors from far and near.

Continue your journey to Siena Cathedral, one of the city’s most captivating spots that you shouldn’t miss. Another great site to visit is the underrated Pubblico Palace. When you're finished at the palace, Piazza Del Campo awaits your visit. This public square is a visually striking highlight on today's itinerary. Last up is a monument - the underrated Tower Of Mangia.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Get ready to discover some of the most iconic wonders in Siena, including an archeological site, a monument, and a public square. Start your day at Colosseum. This historic archeological site is a timeless place to see in Siena. Then, wander over to Arch Of Constantine. If detailed sites excite you, this monument will be right up your alley. Nearby, you’ll also find Roman Forum. This picture-perfect archeological site is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Del Popolo 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 awe-inspiring Altare Della Patria. Take a moment to appreciate the fascinating details of this interesting monument.

At the end of the day, you will drive to Rome, 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 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.

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!

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.

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.

Start your day with a visit to Vatican Museums. This timeless art museum is a must-visit in the city.

One of the best things about exploring Rome 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 St. Peter's Basilica, a globally renowned major basilica in the city. If you’re up for more discoveries, don’t forget to reserve some time for Campo De' Fiori and Piazza Navona.

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

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.

Make sure to reserve a table at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day 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.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, romantic experiences, and natural wonders. Start at Villa Borghese, a spectacular park in the city. Then, head to Spanish Steps and soak in the ambiance of this romantic public square.

There are many interesting places to see in Rome, and when you are ready for more, go to Piazza Di Spagna. This is one of the city’s most wondrous history-steeped spots of interest. After exploring the public square, visit the wondrous Trevi Fountain. Not far away, you'll also find Pantheon. This monument is a monumental highlight in Rome. Before wrapping up your self-guided sightseeing tour, head to Castel Sant'angelo, a top-rated castle 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 lovely dining experience at Hotel de Russie, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at La Taverna Italiana, 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 The Parrot Bar. It’s yet another ideal choice to enhance your time in Rome tonight.

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.

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

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Naples. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Naples. You will spend 2 nights here for some well-deserved relaxation.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Castel Nuovo. This stunning castle is a highlight of any visit in the city. Then, enjoy Spaccanapoli, another visually striking attraction that never fails to captivate visitors. Next, head over to Cappella Sansevero, one of the city’s most locally renowned attractions, known for its detailed 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, a spectacular public square, and take a stroll around the area.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Naples. Naples offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Don’t miss out on dining 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.

Let the evening flow smoothly from dinner to drinks at Happening Cocktail Bar, a top-rated bar in the area. For other recommendations, Shanti Art Musik Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Gran Caffè Gambrinus offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences 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!

Start your day at Archaeological Park Of Pompeii. This awe-inspiring archeological site is an interesting place to see in Naples. Then, wander over to Amphitheatre Of Pompeii. If culturally significant sites excite you, this archeological site will be right up your alley.

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

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

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

Unwind after your meal by stepping into Archivio Storico - Cocktail Bar & Wonderfood. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Archeobar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Babette Pub, another top-rated bar in the area.

Say good night to Naples and look forward to another great day of your road trip 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.

Get ready for an exciting day in Naples. Today’s sightseeing agenda includes a church, a castle, and a public square. Begin your adventure at Basilica Of Santa Maria Degli Angeli. This is an interesting church you should not miss. Another must-see is Basilica Of San Francesco D'assisi, a locally renowned church in Naples.

When you’re ready for the next sight, head to Rocca Maggiore. From there, take a leisurely stroll to Piazza Del Comune, another of the village’s increasingly popular attractions.

When you’re done exploring for the day, you’ll drive to your hotel in Santa Maria degli Angeli. Check in and spend some time relaxing before you head out to tour the town.

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.

With its reputation for pleasing customers, it’s a fantastic choice for tonight in Santa Maria degli Angeli.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a well-loved spot among locals and tourists.

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

Dive into day 13 of your remarkable road trip in Italy. Today you will explore City of San Marino, 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 Rimini. You’ll stay here for 1 night.

Start by visiting State Museum Of San Marino, a prime spot to begin your journey.

We also recommend visiting Guaita Tower, a notable point of interest. Nearby, you'll also find Monte Titano, ready to add charm to your journey.

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

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

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 culinary experience with a visit to some of the most celebrated bars in the area. For instance, Caffè Cavour stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Ilde - Il Baretto Della Buona Piadina offers an ideal atmosphere to enjoy the pleasures of the night. Bar Malatesta is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!