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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Milan. You’ll stay here for 3 nights.

Bologna is home to plenty of attractions that offer fun adventures, breathtaking views, and photo-friendly spots! Start at Two Towers, an interesting monument that is worthwhile a visit in the city. Nearby, you’ll find Villa Ghigi, enchanting visitors with its mesmerizing appeal. Continue your exploration at Piazza Santo Stefano. This public square is one of the city’s most increasingly popular spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit International Museum And Library Of Music.

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

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and modern cuisine in the city.

Continue your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun 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.

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.

Milan is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and photo-friendly spots! Start at Piazza Gae Aulenti, an interesting public square that is worthwhile a visit in the city. Nearby, you’ll find Duomo Di Milano Museum, enchanting visitors with its history-steeped appeal. Continue your exploration at Royal Palace Of Milan. This palace is one of the city’s most locally renowned spots.

Enjoy the freedom of exploring Milan at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Galleria Vittorio Emanuele Ii. After exploring the shopping mall, head to the locally renowned La Scala.

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.

After your meal, keep the night alive at a bar like Kilburn Cocktail Bar Milano, known for its lively atmosphere. Bar Frida is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, The Friends Pub Milano offers an excellent atmosphere for those looking to amp up the evening.

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.

Today’s itinerary in Milan covers several incredible sights, including a church, an art gallery, a castle, a park, a monument and much more! Start your adventure at Santa Maria Delle Grazie Church. This popular church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the photogenic wonders of Pinacoteca Di Brera, a must-see art gallery in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Sforzesco Castle Art Library. This impressive castle offers an enriching experience. For a change of pace, head to Parco Sempione, where you can take in majestic features. Conclude your self-guided sightseeing tour with a visit to Arch Of Peace. These sights offer a fulfilling end to a perfect day.

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.

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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

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

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Milan and Genoa. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await! Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is the perfect place to start. This museum is one of the most popular places to visit in Milan.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Aquarium Of Genoa. This picture-perfect aquarium is a highly recommended experience. Visit these for an interesting touch to your journey.

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

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.

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.

Cap off your dinner by heading to Jeffer Cocktails & Friends, ideal for a leisurely evening with a drink in hand. Le Parisien Wine Bar is another bar that offers an enjoyable setting. Similarly, Las Volta Cocktailbar is also a popular place to go on a night out, perfect for relaxing and socializing.

Head back to your accommodation in Pisa and get some rest in preparation for another magical day of your road trip 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.

Start your adventure at Knights' Square. This curiosity-inducing public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Leaning Tower Of Pisa located in Pisa for another exciting encounter.

Next, immerse yourself in the setting of Angelo Caduto. After the sightseeing destination, continue your tour of the city with a visit to Piazza Del Duomo, Pisa. Visitors usually appreciate the historic features of this public square. Next up is Pisa Cathedral, a highly recommended church.

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.

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

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

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.

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 7 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 Vatican City. In the evening, you’ll end up in Rome, where you will stay for 5 nights.

Start your day at Sistine Chapel. Then, wander over to St. Peter's Basilica. Nearby, you’ll also find Saint Peter's Square.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Vatican Museums is a timeless spot in the city that will captivate you with its unique charm.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome 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 Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended place to eat in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition and a delicious mediterranean and creative menu.

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.

Raise your glass and celebrate another amazing day 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.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Castel Sant'angelo. This majestic castle is a highlight of any visit in the city. Then, enjoy Campo De' Fiori, another eye-catching attraction that never fails to captivate visitors. Next, head over to Piazza Navona, one of the city’s most globally renowned attractions, known for its enchanting features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This heritage-rich monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Largo Di Torre Argentina, a captivating archeological site, and take a stroll around the area.

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 highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent 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.

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

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.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, scenic views, and picturesque spots. Start at Archbasilica Of St. John Lateran, a popular church in the city. Then, head to Basilica Di Santa Maria Maggiore and soak in the ambiance of this culturally significant church.

There are many interesting places to see in Rome, and when you are ready for more, go to Trevi Fountain. This is one of the city’s most globally renowned enchanting spots of interest. After exploring the monument, visit the globally renowned Piazza Di Spagna. Not far away, you'll also find Spanish Steps. This public square is a majestic highlight 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 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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

Savor another day of unforgettable experiences 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Villa Borghese. This impressive park provides an insightful glimpse into the city's identity. Next, discover Passeggiata Del Pincio, an enchanting park, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Del Popolo, a top-rated public square. When you’re done, don’t forget to make a stop at the locally renowned Circus Maximus. Round off your day at Orange Garden, another gem in Rome with visually striking 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.

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.

Treat yourself to a delightful dinner at Sofitel Roma Villa Borghese, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Centro? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Tema as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

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 wondrous Colosseum and allow yourself time to explore. Just a short distance away you'll find your next stop, Roman Forum, an UNESCO world heritage-listed 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 notable Capitoline Museums. When you're finished at the museum, Altare Della Patria awaits your visit. This monument is a culturally significant 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.

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

Enjoy a lovely meal at Ristorante Va. Do. , a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Giulia Restaurant is another top choice with a popular menu. You could also check for a table at L'Archeologia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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

Experience an unparalleled adventure on day 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Arezzo. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a church and a public square. Begin your adventure at San Francesco, Arezzo. This is an often recommended church you should not miss. Another must-see is Santa Maria Della Pieve, an often recommended church in Rome.

When you’re ready for the next sight, head to Piazza Grande.

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

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.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean 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 Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international 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 Florence.

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

Relax and recharge in preparation for another adventurous day 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.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Florence on today’s itinerary. First up is the widely recognized public square, Piazza Della Signoria. Afterward, continue to Palazzo Vecchio, a palace every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Uffizi Gallery. This widely recognized art gallery is an essential stop. Following that, head to Ponte Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, a famous observation deck 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 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 lovely dining experience at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

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

Dive into day 14 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 Bologna. You’ll stay here for 1 night.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most impressive attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This grand church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Dell'accademia and learn what makes this photogenic art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the well-known Central Market. After exploring the food market, head to Basilica Di Santa Maria Novella, Firenze (fi). This well-known church is a highlight in Florence.

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.

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

To truly maximize your evening out, consider visiting Lime Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Macondo - Cocktail Bar, another bar with an inviting ambiance. Similarly, Bar Onda Marina By Night also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Savor another day of unforgettable experiences in Italy!