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

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 3 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Two Towers. This interesting monument provides an insightful glimpse into the city's identity. Next, discover Villa Ghigi, a serene park, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Santo Stefano, a frequently visited public square. When you’re done, don’t forget to make a stop at the locally appreciated International Museum And Library Of Music.

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

Set out on a gastronomic journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. For a different taste, head over to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Il Luogo Aimo e Nadia, a highly rated local gem known for its exquisite italian contemporary and modern menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

Extend your evening after a delightful meal by visiting Nottingham Forest, which offers the perfect atmosphere for a night out. Moreover, Armani/bamboo Bar is another popular option for a drink or two. Likewise, Mag Cafe 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.

Day 3 of your road trip will take you to the best attractions Milan has to offer. Cherish the 2 nights you have left in Milan by discovering the best things there are to see and do in the city.

Start by visiting Piazza Gae Aulenti, a prime spot to begin your journey. This instagrammable public square is sure to impress. Next on your list is Duomo Di Milano Museum, another must-visit landmark and timeless church renowned for its visually striking features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to Royal Palace Of Milan. This visually striking palace is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Galleria Vittorio Emanuele Ii, a famous shopping mall. Nearby, you'll also find La Scala, ready to add charm to your journey.

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

Enjoy a lovely dining experience at Dessert Bar Milano, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Radisson Blu Hotel Milan, 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 Ristorante Qui Si Mangia. It’s yet another ideal choice to enhance your time 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.

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

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Milan allows for both. Start by heading to Santa Maria Delle Grazie Church. This interesting church provides an insightful glimpse into the city's identity. Next, discover Pinacoteca Di Brera, a visually striking art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Sforzesco Castle Art Library, a famous castle. When you’re done, don’t forget to make a stop at the famous Parco Sempione. Round off your day at Arch Of Peace, another gem in Milan with remarkable features to discover.

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 Milan. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at 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 enjoying a fulfilling meal, continue your evening at Bhangrabar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Rufus Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Ostello Bello Grande provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Milan and Genoa, 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 Pisa. You’ll stay here for 1 night.

Discover a day packed with fun adventures, photo-friendly spots, and history-rich sites in Milan. Begin your sightseeing with Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This well-known museum is one of the top attractions in the city. Proceed to The City Of Children And Young, another must-visit attraction.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Aquarium Of Genoa. This extraordinary aquarium is a traveler-favorite.

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.

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

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Jeffer Cocktails & Friends is an excellent place to start. You could also check out Le Parisien Wine Bar, offering a different kind of charm. A last recommendation for the day is Las Volta Cocktailbar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Pisa. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, breathtaking views, and photo-friendly spots. Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Knights' Square is the first of them. Spend some time admiring this culturally significant public square before continuing your journey. Leaning Tower Of Pisa is your next stop. This world-famous monument is one of the best-rated sights in Pisa.

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 Angelo Caduto. To round off your sightseeing experience, visit Piazza Del Duomo, Pisa and Pisa Cathedral.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

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.

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

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Vatican City. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 5 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Sistine Chapel is the perfect place to start. This chapel is one of the most widely recognized places to visit in Siena.

Nearby, you'll also find Vatican Museums. Visit these for an interesting touch to your journey.

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 and reflect on the day's adventures.

Experience a taste of local culinary excellence while in Rome by securing a table at La Pergola. An esteemed 3-star Michelin restaurant, it features an exceptional mediterranean and contemporary menu. For an alternative taste experience, visit Il Pagliaccio, famous for its scrumptious creative and innovative dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Enoteca La Torre, a local favorite celebrated for its exquisite mediterranean and creative cuisine in Rome. Located in the heart of the city, this 2-star Michelin restaurant is an ideal pick for mediterranean and creative cuisine lovers seeking top-notch culinary experiences.

Continue the enjoyment post-dinner at La Botticella Of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Almalu Trastevere offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Viminale Di Pepi Maurilio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 8 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 4 nights and discover all the best things to see and do in the area.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming city of Rome. Your adventure starts at Castel Sant'angelo, an impressive local hot spot. Another notable attraction to explore is Campo De' Fiori. This widely recognized public square is known for its awe-inspiring appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Navona. This history-steeped public square offers a fascinating experience that many visitors find memorable. Pantheon is also worth visiting, along with Largo Di Torre Argentina. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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 meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

Round off your dining experience by visiting Sant' Eustachio Caffè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yellowsquare Rome, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 3 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Archbasilica Of St. John Lateran. This culturally significant church is sure to ignite your curiosity. Next, dive into the heritage-rich features of Basilica Di Santa Maria Maggiore, a must-visit church 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 Trevi Fountain, a timeless monument. For a change of scene, check out Piazza Di Spagna, known for its history-steeped features. We also recommend visiting Spanish Steps. This public square is a must for anyone looking to experience the city to the fullest.

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 Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at The Apartment Bar Roma after your meal, a hub for lively evenings and memorable moments. Or, head to Hotel Hassler Roma for a great selection of flavorful drinks and a charming setting.

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

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Rome is home to plenty of attractions that offer fun adventures, romantic experiences, and natural wonders! Start at Villa Borghese, an extraordinary park that is worthwhile a visit in the city. Nearby, you’ll find Passeggiata Del Pincio, enchanting visitors with its stunning appeal. Continue your exploration at Piazza Del Popolo. This public square is one of the city’s most astonishing 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 Circus Maximus. After exploring the archeological site, head to the notable Orange Garden.

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.

Treat yourself to a delicious dinner at Sofitel Roma Villa Borghese, an excellent option for tonight's dining. Looking for something different? Centro offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Tema. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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

Day 11 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Rome is brimming with adventures. Today’s wonderful stops include an archeological site, a public square, a museum, a monument and much more! Begin your sightseeing adventure at the world-famous Colosseum and allow yourself time to explore. Just a short distance away you'll find your next stop, Roman Forum, a historic archeological site that draws visitors from far and near.

Continue your journey to Capitoline Hill, one of the city’s most captivating spots that you shouldn’t miss. Another great site to visit is the popular Capitoline Museums. When you're finished at the museum, Altare Della Patria awaits your visit. This monument is a historic highlight on today's itinerary.

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.

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

Raise your glass and celebrate another amazing 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 Arezzo. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Today, you'll explore some of the most beautiful places in Rome, including a church and a public square. Start your day with a visit to San Francesco, Arezzo. This frequently visited church is a must-visit in the city. When you’re ready for your next discovery, continue to Santa Maria Della Pieve, which may be one of the most history-steeped places you will experience today.

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 Piazza Grande, an interesting public square 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.

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

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences in Italy!

On day 13 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and breathtaking views. Start at Piazza Della Signoria, an extraordinary public square in the city. Then, head to Palazzo Vecchio and soak in the ambiance of this enchanting palace.

There are many interesting places to see in Florence, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most widely recognized picture-perfect spots of interest. After exploring the art gallery, visit the timeless Ponte Vecchio. Not far away, you'll also find Piazzale Michelangelo. This observation deck is an enchanting highlight in 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.

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

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

Embark on another extraordinary experience on day 14 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

Savor the day by visiting some of the best places to see in Florence, including a church, an art gallery, and a food market. Start your adventure at Cathedral Of Santa Maria Del Fiore. This widely recognized church is a must-visit for travelers looking for a unique holiday experience. Make your way to Galleria Dell'accademia located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Central Market. Its instagrammable features will captivate you. After the food market, continue your tour of the city with a visit to Basilica Di Santa Maria Novella, Firenze (fi). Visitors usually appreciate the enchanting features of this church.

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.

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

Dive into a culinary adventure like no other in Bologna by booking a table at Ahimè. This popular restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another culinary dining option, venture to I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Trattoria di Via Serra, a top local restaurant known for its tantalizing emilian menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

After enjoying a fulfilling meal, continue your evening at Lime Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Macondo - Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Onda Marina By Night provides an excellent environment for a relaxed and enjoyable evening.

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