14-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Milan, Pisa, Siena, Rome, and Florence

On day 2 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 Milan, where you will stay for 3 nights.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Bologna on today’s itinerary. First up is the frequently visited public square, Piazza Santo Stefano. Afterward, continue to Porta Maggiore.

As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Devotional Portico Of St. Luke. This underrated monument is an essential stop that should not be missed. Following that, head to Two Towers, another must-visit site that will enhance your experience. Lastly, visit Arco Del Meloncello and learn why this monument is renowned as one of the city's most increasingly popular attractions.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and spend some time relaxing before you head out to tour the city.

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

Dive into a culinary adventure like no other in Milan by booking a table at Enrico Bartolini al Mudec. This popular restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another culinary dining option, venture to Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Il Luogo Aimo e Nadia, a top local restaurant known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Continue the enjoyment post-dinner at Nottingham Forest, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Armani/bamboo Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Mag Cafe. 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 3 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 2 nights and discover all the best things to see and do in the area.

Start by visiting La Scala, a prime spot to begin your journey. This historic opera house is sure to impress. Next on your list is Piazza Della Scala, another must-visit landmark and frequently visited public square renowned for its enchanting features.

While exploring and sightseeing, take time to savor the ambiance of Milan by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Galleria Vittorio Emanuele Ii. This awe-inspiring shopping mall is a remarkable attraction that offers a unique experience. Duomo Di Milano Museum also adds charm to your journey, and Royal Palace Of Milan wraps up your day with its heritage-rich appeal.

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 Milan, 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 Dessert Bar Milano, a top pick for dinner tonight. Alternatively, Radisson Blu Hotel Milan beckons with its unique menu offerings. Also, consider Ristorante Qui Si Mangia. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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

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

Day 4 offers a multitude of experiences. You will stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Gae Aulenti is the first of them. Spend some time admiring this eye-catching public square before continuing your journey. Pinacoteca Di Brera is your next stop. This popular art gallery is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Sforzesco Castle Art Library. This breathtaking castle is a sight to behold. To round off your sightseeing experience, visit Parco Sempione and Arch Of Peace.

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.

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

Make sure to reserve a table at Bice Restaurant, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Alto Ristorante, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bhangrabar, known for its inviting atmosphere. Rufus Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Ostello Bello Grande provides a great setting to enjoy the night away.

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Milan and Genoa. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Start by visiting Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a prime spot to begin your journey. This eye-catching museum is sure to impress.

While exploring and sightseeing, take time to savor the ambiance of Milan by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Aquarium Of Genoa. This stunning aquarium is a remarkable attraction that offers a unique experience.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Pisa. Pisa 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 Pisa. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

To truly maximize your evening out, consider visiting Jeffer Cocktails & Friends after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Le Parisien Wine Bar, another bar with an inviting ambiance. Similarly, Las Volta Cocktailbar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Pisa, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Siena. You’ll stay here for 1 night.

Set out on a day brimming with fun adventures, breathtaking views, and picturesque spots. Start at the beloved Knights' Square, a breathtaking public square in Pisa. Next, go to Leaning Tower Of Pisa.

Piazza Del Duomo, Pisa is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Pisa Cathedral, one of the most UNESCO world heritage-designated places to visit in Pisa.

At the end of the day, you will drive to Siena, 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena 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!

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 Vatican City. 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 4 nights.

Start your adventure at Sistine Chapel. This spectacular chapel is a must-visit for travelers looking for a unique holiday experience. Make your way to St. Peter's Basilica located in Siena for an enchanting atmosphere.

Next, immerse yourself in the setting of Saint Peter's Square. After the square, continue your tour of the city with a visit to Vatican Museums.

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 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.

Experience a symphony of flavors at La Pergola in Rome by securing a reservation in advance. Renowned for its 3-star Michelin distinction, La Pergola delights its guests with its exceptional variety of meals showcasing delicious mediterranean and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Il Pagliaccio, acclaimed for its delectable creative and innovative specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Enoteca La Torre, a top-rated restaurant known for its outstanding menu. Known as a top-rated 2-star Michelin establishment, it's a top choice for mediterranean and creative cuisine in the city.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Day 8 of your road trip will take you to the best attractions Rome has to offer. Cherish the 3 nights you have left in Rome by discovering the best things there are to see and do in the city.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Altare Della Patria. This remarkable monument is sure to ignite your curiosity. Next, dive into the masterful features of Capitoline Hill, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Colosseum, an iconic archeological site. For a change of scene, check out Roman Forum, known for its culturally significant features.

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.

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

Enjoy a delicious meal 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.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Belvedere Del Gianicolo. This locally renowned observation deck is a visually striking place to see in Rome. Continue your discovery at Campo De' Fiori, a picture-perfect public square 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 Piazza Navona. This iconic public square offers a symbolic encounter with Rome. Castel Sant'angelo is the last of our recommendations for today. 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.

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 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.

Treat yourself to a wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Continue your lively evening at The Apartment Bar Roma, a perfect place for winding down or revving up the night, depending on which mood you’re in. Hotel Hassler Roma is another excellent bar that offers a great selection of drinks to suit any mood.

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

On day 10 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.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Rome. Begin your sightseeing with Spanish Steps. This famous public square is one of the top attractions in the city. Proceed to Piazza Di Spagna, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Trevi Fountain. This wondrous monument is a traveler-favorite. Not far away, you’ll find Orange Garden, another key site on your sightseeing itinerary. Conclude your day at Circus Maximus and uncover why it's recognized as one of the city's most captivating attractions.

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.

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

Enjoy a delicious meal at Sofitel Roma Villa Borghese, a highly-rated dining destination in Rome. If you're eager to try something different, consider Centro, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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

On day 11 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Rome is home to plenty of attractions that offer fun adventures, photo-friendly spots, and historic treasures! Start at Largo Di Torre Argentina, a notable archeological site that is worthwhile a visit in the city. Nearby, you’ll find Pantheon, enchanting visitors with its heritage-rich appeal. Continue your exploration at Piazza Del Popolo. This public square is one of the city’s most impressive 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 Passeggiata Del Pincio. After exploring the park, head to the widely recognized Villa Borghese. This park will wrap up today’s self-guided sightseeing tour in the city.

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

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Palagio, a top local spot known for its tantalizing italian contemporary menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Day 12 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Florence is brimming with adventures. Today’s wonderful stops include an observation deck, a church, a public square, an art gallery, a historical landmark and much more! Begin your sightseeing adventure at the famous Piazzale Michelangelo. Just a short distance away is Basilica Of Santa Croce In Florence, a culturally significant church that draws visitors from far and near.

Continue your journey to Piazza Della Signoria, one of the city’s most widely recognized spots that you shouldn’t miss. Another great site to visit is the extraordinary Uffizi Gallery. Last up on today’s itinerary is a historical landmark. Make your way to Ponte Vecchio for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Florence.

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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Savor another day of unforgettable experiences in Italy!

On day 13 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 Florence. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Cathedral Of Santa Maria Del Fiore. This extraordinary church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Galleria Dell'accademia, one of the city’s most promising highlights.

Next, check out Central Market, one of the most notable places to see in Florence. This food market is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Basilica Di Santa Maria Novella, Firenze (fi). Wander around and soak in the inviting atmosphere this church offers.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Bologna. 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.

Have a memorable dining experience in Bologna by booking a table at Ahimè, renowned as a Bib Gourmand restaurant presenting an exceptional country cooking menu. For a different culinary experience in Bologna, I Portici shines as one of the top destinations, known for its delicious creative and contemporary cuisine. This 1-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Trattoria di Via Serra is known as a top local spot for its delicious emilian cuisine in Bologna. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

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

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