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 an itinerary packed with the best things to see in Rimini. You’ll stay in Rimini for 1 night more, offering you enough time to explore at a relaxed pace.

No visit to Rimini is complete without Spiaggia Libera. This locally appreciated beach is one of the top attractions in the city. Proceed to Parco Federico Fellini, another must-visit attraction.

As you wander through the inviting streets of Rimini, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Domus Del Chirurgo. This underrated archeological site is a traveler-favorite. Not far away, you’ll find Parco Xxv Aprile, another key site on your sightseeing itinerary.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Rimini, it's often a good idea to reserve a table in advance.

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. Known for great service, it’s a fantastic choice for tonight in Rimini.

After savoring a delicious meal, step into the vibrant nightlife at Hobo's, where the evening is just getting started. In the same way, Sunflower City Backpacker offers a unique charm perfect for experiencing the local bar scene in Rimini. Bar Capogiro is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Bologna. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna, where you'll spend 1 night.

Continue your road trip and head to your next destination, Bologna. This car ride takes around 1 hour 27 min.

Pinacoteca Nazionale Di Bologna is a beloved art gallery we recommend visiting today. Discover its standout features before continuing your self-guided tour to Two Towers, a culturally significant monument that’s well-regarded in the area.

Next, stop by Bologna Cathedral, a stunning church. While you’re nearby, don’t forget to visit Fountain Of Neptune, Bologna, a noteworthy and truly unique monument. End your sightseeing at Portici Di Bologna, a locally appreciated street that’s highly recommended by travelers passing through 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.

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

Savor the flavors at Ristorante Ciacco, a top pick for dinner tonight. Alternatively, Ristorante Ballarini beckons with its unique menu offerings. Also, consider Sfoglia Rina. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, another top-rated place in the area.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 2 nights.

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Florence. Expect your car journey to take a minimum of 1 hour 27 min. When you arrive in Florence, it's time to take a break from the road.

One of our top recommendations for your sightseeing is The Boboli Gardens. Spend some time admiring the masterful features of the botanical garden before you continue to your next stop. Then, head to Ponte Vecchio. This globally renowned historical landmark is a traveler-favorite in the city.

If you're keen to see more, continue to Uffizi Gallery. Feed your curiosity by learning something new about the art gallery. Next, take your journey to Basilica Of Santa Croce In Florence, a locally renowned church. Conclude your sightseeing at Palazzo Vecchio, known for its culturally significant features.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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

Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Pisa. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 14 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Spend your afternoon discovering Santa Maria Della Spina, an intriguing church known for its visually striking features. Next, continue your sightseeing at Knights' Square, a beloved public square.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Leaning Tower Of Pisa and uncover the details of this historic monument. Make sure to also explore Pisa Cathedral, a frequently visited church. For your last stop, consider Campo Santo, a noteworthy cemetery that many travelers find worth the detour.

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

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

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.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Siena. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 10 min.

For a more meaningful self-guided tour of the city's best attractions, visit Fortezza Medicea (siena), an often recommended monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Basilica Of San Domenico and admire its culturally significant features.

When you’re ready, continue to Siena Cathedral, a locally renowned church beloved by locals and tourists alike. Don't miss out on Pubblico Palace, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Piazza Del Campo, an enchanting place to see that you won’t regret spending some extra time discovering.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and look forward to more memorable moments to come!

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Set your GPS to Rome and hit the road. Expect a journey of approximately 2 hours 42 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Rome beckons with new experiences!

Our first attraction recommendation in Rome is Colosseum, a wondrous archeological site that draws attention for its culturally significant features. Spend some time soaking in the atmosphere before continuing to Arch Of Constantine, a breathtaking monument that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Roman Forum, a wondrous archeological site that offers a unique experience. Be sure to also explore Piazza Del Popolo, a nearby public square, highly recommended by other travelers. End your self-guided tour at Altare Della Patria, a historic monument and the perfect final attraction in Rome.

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 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.

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

Head back to your accommodation in Rome and get some rest to prepare for another magical day of your road trip in Italy.

On day 8 of your road trip, you’ll start and end your day in Rome, where you have 2 nights left to stay.

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights.

Enjoy all that Campo De' Fiori has to offer. This is a top-rated public square you should not miss. Another must-see is Piazza Navona, an iconic public square in Rome.

Fasten your seatbelt and make your way to your next stop — Vatican City, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Vatican City may take around 12 min without traffic disruptions. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Vatican Museums, an iconic art museum in Vatican City. This famous chapel is a top recommendation in the area.

When you’re ready to explore more, St. Peter's Basilica is an excellent choice.

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.

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

Savor another day of unforgettable experiences in Italy!

Day 9 of your road trip across Italy promises a magnificent time exploring what to see in 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 brimming with adventures.

Check out the widely recognized park, Villa Borghese. Afterward, continue to Spanish Steps, a public square 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 Piazza Di Spagna. This globally renowned public square is an essential stop. Following that, head to Trevi Fountain, another must-visit site that will enhance your experience. Don’t forget to stop by Pantheon, a timeless monument in the city. Finally, end your day with a visit to Castel Sant'angelo, a grand castle that offers the perfect conclusion to your sightseeing of the day.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

Savor another day of unforgettable experiences in Italy!

Your itinerary for day 10 of your road trip in Italy includes 1 stop and features some of the highlights of Naples. At the end of the day, enjoy the comforts of a top-rated hotel in Naples, where you'll spend 2 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Naples may take around 2 hours 31 min. Upon your arrival in Naples, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castel Nuovo, a popular castle that everyone visiting Naples should see. Next, head to Spaccanapoli. This history-steeped street is one of the most increasingly popular attractions in the region.

If you're keen to see more, don’t miss out on Cappella Sansevero, a detailed museum popular among locals as well as travelers. Naples National Archaeological Museum is an excellent attraction to visit next. Spend some time learning more about this interesting museum before you continue your journey. Lastly, visit Piazza Del Plebiscito, an enchanting public square and a top attraction in the city.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

After enjoying a fulfilling meal, continue your evening at Happening Cocktail Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Shanti Art Musik Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Gran Caffè Gambrinus provides an excellent environment for a relaxed and enjoyable evening.

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

Greet day 11 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Naples, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Pompei.

When you’ve had your share of Naples, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pompei. Your travel time is around 27 min.

Set out on a self-guided sightseeing tour at Archaeological Park Of Pompeii and explore the picture-perfect features. Next, make your way to Amphitheatre Of Pompeii, another highlight in Pompei.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Naples, it's often a good idea to reserve a table in advance.

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.

Keep the evening going at Archivio Storico - Cocktail Bar & Wonderfood, a great choice for enjoying the after-dinner hours with a drink. You could also go to Archeobar, which offers a similarly pleasant setting and great drinks. Another option is Babette Pub, which provides an inviting environment for unwinding after a busy day out.

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

Dive into day 12 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Santa Maria degli Angeli. At the end of the day, you’ll unwind at one of the finest accommodations in Santa Maria degli Angeli, where you'll spend 1 night.

Fasten your seatbelt and make your way to your next stop — Santa Maria degli Angeli, home to many well-known sights in the region. Keep in mind that your travel time from Naples to Santa Maria degli Angeli may take around 3 hours 58 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

Set out on a self-guided sightseeing tour at Basilica Of Santa Maria Degli Angeli and explore the stunning features.

Fasten your seatbelt and make your way to your next stop — Santa Maria degli Angeli, home to many well-known sights in the region. Keep in mind that your travel time from Santa Maria degli Angeli to Santa Maria degli Angeli may take around 9 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Basilica Of San Francesco D'assisi, an interesting church that everyone visiting Santa Maria degli Angeli should see. Next, head to Rocca Maggiore. This visually striking castle is one of the most often recommended attractions in the region.

If you're keen to see more, don’t miss out on Piazza Del Comune, an UNESCO world heritage-designated public square popular among locals as well as travelers.

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

Santa Maria degli Angeli is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Santa Maria degli Angeli.

Keep the evening going at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a great choice for enjoying the after-dinner hours with a drink.

Savor another day of unforgettable experiences in Italy!

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

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in City of San Marino.

City of San Marino’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Santa Maria degli Angeli behind. This drive usually takes around 2 hours 44 min. City of San Marino welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to State Museum Of San Marino, a curiosity-inducing museum in City of San Marino. This locally appreciated point of interest is a top recommendation in the area.

When you’re ready to explore more, Basilica Del Santo is an excellent choice. Next, continue your sightseeing at the captivating Guaita Tower and discover what makes this sightseeing destination unique.

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.

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

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 day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.