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

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Milan, where you’ll be staying for 3 nights.

Enjoy all that Two Towers has to offer. This is a locally renowned monument you should not miss. Another must-see is Villa Ghigi, an often recommended park in Bologna.

When you’re ready for the next sight, head to Piazza Santo Stefano. From there, take a leisurely stroll to International Museum And Library Of Music, another of the city’s intriguing attractions.

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

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

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for italian contemporary and modern foodies seeking culinary excellence.

Following your dinner, dive into the local bar culture at Nottingham Forest. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Armani/bamboo Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Mag Cafe provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Say good night to Milan and look forward to another great day of your road trip 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 the city and use the provided itinerary to discover what to see in Milan.

Milan is brimming with adventures.

Make a stop at Piazza Gae Aulenti. This interesting public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Duomo Di Milano Museum located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Royal Palace Of Milan. Its eye-catching features will captivate you. After the palace, continue your tour of the city with a visit to Galleria Vittorio Emanuele Ii. Visitors usually appreciate the romantic features of this shopping mall. Next up is La Scala, a highly recommended opera house.

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.

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

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.

Following your dinner, dive into the local bar culture at Kilburn Cocktail Bar Milano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Frida, the perfect place for those looking to experience the best of the nightlife. Similarly, The Friends Pub Milano provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 4 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

Santa Maria Delle Grazie Church makes a great addition to your morning plans. This well-known church is a photogenic place to see in Milan. Continue your discovery at Pinacoteca Di Brera, a heritage-rich art gallery with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Sforzesco Castle Art Library. This famous castle offers a breathtaking encounter with Milan. Next, make your way to Parco Sempione to add another highlight to your day. After that, visit Arch Of Peace, a well-known monument that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Milan.

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 Milan, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

After savoring a delicious meal, step into the vibrant nightlife at Bhangrabar, where the evening is just getting started. In the same way, Rufus Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Ostello Bello Grande is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Relax and look forward to more memorable moments to come!

Your itinerary for day 5 of your road trip in Italy includes 2 stops and features some of the highlights of Milan and Genoa. At the end of the day, enjoy the comforts of a top-rated hotel in Pisa, where you'll spend 1 night.

Make time for Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a popular museum that is worthwhile a visit in the city.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Genoa. This drive usually takes around 1 hour 53 min, without any stops or traffic disruptions.

When you're ready for some sights, head to The City Of Children And Young, an intriguing museum in Genoa. This famous aquarium is a top recommendation in the area.

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

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

Savor the flavors at Anima di Grano Pizzeria Napoletana Pisa Italy, a top pick for dinner tonight. Alternatively, il Mercante beckons with its unique menu offerings. Also, consider La Ghiotteria. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

As the sun sets, rest up and recharge for the next leg of your road trip 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 Pisa. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

Awaiting your discovery is the frequently visited Knights' Square, a picture-perfect public square in Pisa. Next, go to Leaning Tower Of Pisa.

Piazza Del Duomo, Pisa is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Pisa Cathedral, one of the most historic places to visit in Pisa.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Siena. Siena 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

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.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

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. Vatican City are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 5 nights.

Set your GPS to Vatican City, Vatican City and hit the road. Expect a journey of approximately 2 hours 40 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Vatican City beckons with new experiences!

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 Saint Peter's Square, an interesting square that offers a unique experience. Be sure to also explore Vatican Museums, a nearby art museum, highly recommended by other travelers.

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

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

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 to another unforgettable day in Italy!

On day 8 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 4 nights.

Your adventure in Rome is only getting started when you visit Castel Sant'angelo, a widely recognized local hot spot. Another notable attraction to explore is Campo De' Fiori. This top-rated public square is known for its enchanting 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 enchanting 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 experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Sant' Eustachio Caffè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yellowsquare Rome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino is also a great option that provides a perfect setting for a relaxing evening.

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

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

Make time for Archbasilica Of St. John Lateran, a well-known church that is worthwhile a visit in the city. Nearby, you’ll find Basilica Di Santa Maria Maggiore, enchanting visitors with its heritage-rich appeal. Continue your exploration at Trevi Fountain. This monument is one of the city’s most wondrous 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 Piazza Di Spagna. After exploring the public square, head to the astonishing Spanish Steps.

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.

Rome 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 Rome.

Don’t miss out on dining at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

Say good night to Rome and look forward to another great day 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 the city and use the provided itinerary to discover what to see in Rome.

Enjoy all that Villa Borghese has to offer. This is an astonishing park you should not miss. Another must-see is Passeggiata Del Pincio, a well-known park in Rome.

When you’re ready for the next sight, head to Piazza Del Popolo. From there, take a leisurely stroll to Circus Maximus, another of the city’s popular attractions. We recommend continuing your self-guided tour at Orange Garden, a romantic place of interest in the city.

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.

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.

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

Day 11 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Check out the globally renowned archeological site, Colosseum. Afterward, continue to Roman Forum, an archeological site 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 Capitoline Hill. This popular public square is an essential stop. Following that, head to Capitoline Museums, another must-visit site that will enhance your experience. Don’t forget to stop by Altare Della Patria, a captivating monument in the city.

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 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 a lovely dining experience at Ristorante Va. Do. , a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Giulia Restaurant, 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 L'Archeologia. It’s yet another ideal choice to enhance your time in Rome tonight.

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

Dive into day 12 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Arezzo. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 2 nights.

As you explore Arezzo’s charming streets, take in the lively atmosphere and get to know the character of the city.

After soaking in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Arezzo. Expect your car journey to take a minimum of 2 hours 37 min. When you arrive in Arezzo, it's time to take a break from the road.

One of our top recommendations for your sightseeing is San Francesco, Arezzo. Spend some time admiring the culturally significant features of the church before you continue to your next stop. Then, head to Santa Maria Della Pieve. This beloved church is a traveler-favorite in the city.

If you're keen to see more, continue to Piazza Grande. Feed your curiosity by learning something new about the public square.

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

Florence 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 Florence.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 13 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 1 night.

Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Piazza Della Signoria leaves a lasting impression. This public square is one of the most spectacular places to visit in Florence. Next, head to Palazzo Vecchio, a popular palace, known for its enchanting features.

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 Uffizi Gallery. This romantic art gallery is a highly recommended experience. Nearby, you'll also find Ponte Vecchio and Piazzale Michelangelo Visit these for an interesting touch to your journey.

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.

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

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

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.

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

On day 14 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 Bologna, where you’ll be staying for 1 night.

No visit to Florence is complete without Cathedral Of Santa Maria Del Fiore. This widely recognized church is one of the top attractions in the city. Proceed to Galleria Dell'accademia, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Central Market. This well-known food market is a traveler-favorite. Not far away, you’ll find Basilica Di Santa Maria Novella, Firenze (fi), another key site on your sightseeing itinerary.

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

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 Bologna, it's often a good idea to reserve a table in advance.

Prepare for an extraordinary culinary adventure in Bologna by booking a table at Ahimè, a Bib Gourmand restaurant that boasts an exceptional country cooking menu. For a different flavor experience, head to I Portici, renowned for its delectable creative and contemporary dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Trattoria di Via Serra, a local gem known for its delightful emilian cuisine in Bologna. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Lime Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Macondo - Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Bar Onda Marina By Night is also a great option that provides a perfect setting for a relaxing evening.

Relax and look forward to more memorable moments to come!