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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Milan, where will spend 3 nights.

Make time for Two Towers, a well-known monument that is worthwhile a visit in the city. Nearby, you’ll find Villa Ghigi, enchanting visitors with its eye-catching appeal. Continue your exploration at Piazza Santo Stefano. This public square is one of the city’s most underrated 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 on today's itinerary, you'll be ready to head to 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.

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.

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.

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.

Savor another day of unforgettable experiences in Italy!

On day 3 of your road trip, you will have an entire day to discover what to see in Milan. You’ll stay in Milan for 2 nights.

To truly experience Milan, make sure to drop by Piazza Gae Aulenti. This captivating public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Duomo Di Milano Museum, one of the city’s best highlights.

Next, check out Royal Palace Of Milan, one of the most locally renowned places to see in Milan. This palace is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Galleria Vittorio Emanuele Ii. Wander around and soak in the history-steeped atmosphere this shopping mall offers. Then, head to La Scala, a top-rated opera house that adds another dimension to your day.

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

Milan 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 Milan.

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.

Keep the excitement of the evening going by visiting a bar or two. Kilburn Cocktail Bar Milano is an excellent place to start. You could also check out Bar Frida, offering a different kind of charm. A last recommendation for the day is The Friends Pub Milano. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Day 4 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Milan.

Santa Maria Delle Grazie Church is perfect for a self-paced visit during the day. This UNESCO world heritage-listed church is sure to impress. Next on your list is Pinacoteca Di Brera, another must-visit landmark and captivating art gallery renowned for its instagrammable 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 Sforzesco Castle Art Library. This stunning castle is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Parco Sempione, an impressive park. Nearby, you'll also find Arch Of Peace, ready to add charm 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.

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.

Treat yourself to a delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

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

Raise your glass to another unforgettable day in Italy!

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.

Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is an ideal stop early in the day. This notable museum is a must-visit in the city.

When you’re ready to jump back into the car and say goodbye to Milan, you’ll hit the road in the direction of Genoa. This drive usually takes around 1 hour 53 min.

Savor the day by heading to The City Of Children And Young, a beloved museum that draws visitors from near and far. When you're done, continue to Aquarium Of Genoa, where you can soak in the mesmerizing surroundings.

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.

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

Enjoy a lovely meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, il Mercante is another top choice with a popular menu. You could also check for a table at La Ghiotteria. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Pisa tonight.

After enjoying a fulfilling meal, continue your evening at Jeffer Cocktails & Friends, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Le Parisien Wine Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Las Volta Cocktailbar provides an excellent environment for a relaxed and enjoyable evening.

Relax and look forward to more memorable moments to come!

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

Knights' Square leaves a lasting impression. This public square is one of the most increasingly popular places to visit in Pisa. Next, head to Leaning Tower Of Pisa, a globally renowned monument, known for its picture-perfect features.

Nearby, you'll also find Piazza Del Duomo, Pisa and Pisa Cathedral Visit these for an interesting touch to your journey.

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

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

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

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

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.

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 2 hours 40 min, without any stops or traffic disruptions.

Sistine Chapel is a spectacular chapel we recommend visiting today.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

Day 8 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Rome for 4 nights more, offering you enough time to explore at a relaxed pace.

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

Check out the famous castle, Castel Sant'angelo. Afterward, continue to Campo De' Fiori, a public square every traveler should visit. As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Piazza Navona. This globally renowned public square is an essential stop. Following that, head to Pantheon, another must-visit site that will enhance your experience. Don’t forget to stop by Largo Di Torre Argentina, a captivating archeological site 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.

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

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences in Italy!

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

Archbasilica Of St. John Lateran makes a great addition to your morning plans. This captivating church is a majestic place to see in Rome. Continue your discovery at Basilica Di Santa Maria Maggiore, a photogenic church 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 Trevi Fountain. This timeless monument offers a visually striking encounter with Rome. Next, make your way to Piazza Di Spagna to add another highlight to your day. After that, visit Spanish Steps, an extraordinary public square 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 Rome.

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.

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 savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

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

On day 10 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 2 nights.

Make a stop at Villa Borghese. This spectacular park is a must-visit for travelers looking for a unique holiday experience. Make your way to Passeggiata Del Pincio located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Piazza Del Popolo. Its enchanting features will captivate you. After the public square, continue your tour of the city with a visit to Circus Maximus. Visitors usually appreciate the culturally significant features of this archeological site. Next up is Orange Garden, a highly recommended park.

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

Enjoy a lovely meal at Sofitel Roma Villa Borghese, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Centro is another top choice with a popular menu. You could also check for a table at Ristorante Tema. As an establishment that consistently gains 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.

Day 11 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Rome.

One of the most iconic attractions included on the itinerary is Colosseum. This UNESCO world heritage-designated archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Roman Forum and learn what makes this UNESCO world heritage-listed archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Capitoline Hill. After exploring the public square, head to Capitoline Museums. This well-known museum is a highlight in Rome. As your day continues, stop by Altare Della Patria, known for its historic features.

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.

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

Relax and look forward to more memorable moments to come!

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.

When you’re ready to jump back into the car and say goodbye to Rome, you’ll hit the road in the direction of Arezzo. This drive usually takes around 2 hours 37 min.

Set out on a self-guided sightseeing tour at San Francesco, Arezzo and explore the heritage-rich features. Next, make your way to Santa Maria Della Pieve, another highlight in Arezzo. When you’re done exploring the church, continue to Piazza Grande, a romantic 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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

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

Day 13 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Whatever your travel style is, Piazza Della Signoria is an essential stop in Florence. This famous public square provides an insightful glimpse into the city's identity. Next, discover Palazzo Vecchio, a grand palace, promising a delightful encounter.

Continue your sightseeing with a visit to Uffizi Gallery, an impressive art gallery. When you’re done, don’t forget to make a stop at the timeless Ponte Vecchio. Round off your day at Piazzale Michelangelo, another gem in Florence with enchanting features to discover.

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.

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.

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.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Bologna, where will spend 1 night.

One of the most extraordinary attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This visually striking church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Dell'accademia and learn what makes this standout art gallery unique.

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

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

If you’re not ready to end the night just yet, Lime Bar offers a perfect venue to relax and savor a drink. Similarly, Macondo - Cocktail Bar is well-suited for those looking to unwind in a social setting. Bar Onda Marina By Night is another excellent spot to enjoy a nightcap after a delightful meal.

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