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

Your itinerary for day 2 of your road trip in Italy includes 1 stop and features some of the highlights of Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 3 nights.

Check out the locally renowned monument, Two Towers. Afterward, continue to Villa Ghigi, a park every traveler should visit. As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Piazza Santo Stefano. This up-and-coming public square is an essential stop. Following that, head to International Museum And Library Of Music, another must-visit site that will enhance your experience.

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.

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

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.

Let the evening flow smoothly from dinner to drinks at Nottingham Forest, a top-rated bar in the area. For other recommendations, Armani/bamboo Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Mag Cafe offers a memorable night with diverse drink options and excellent service.

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

Day 3 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Milan for 2 nights more, offering you enough time to explore at a relaxed pace.

Visiting Piazza Gae Aulenti is always a good idea. This popular public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Duomo Di Milano Museum, a must-see church 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 Royal Palace Of Milan. This notable palace offers an enriching experience. For a change of pace, head to Galleria Vittorio Emanuele Ii, where you can take in enchanting features. Conclude your self-guided sightseeing tour with a visit to La Scala These sights offer a fulfilling end to a perfect 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.

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

Enjoy a delicious meal at Dessert Bar Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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.

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

On day 4 of your road trip, you will have an entire day to discover what to see in Milan. You’ll stay in Milan for 1 night.

Check out the captivating church, Santa Maria Delle Grazie Church. Afterward, continue to Pinacoteca Di Brera, an art gallery every traveler should visit. As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Sforzesco Castle Art Library. This extraordinary castle is an essential stop. Following that, head to Parco Sempione, another must-visit site that will enhance your experience. Don’t forget to stop by Arch Of Peace, a well-known 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.

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

Enjoy a lovely dining experience at Bice Restaurant, 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 Alto Ristorante, 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 Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

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

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 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Milan and Genoa. When you’re not sightseeing, take time to relax at your chosen hotel in Pisa, where you’ll be staying for 1 night.

Start your day at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This standout museum is a captivating place to see in Milan. Then, wander over to The City Of Children And Young. Nearby, you’ll also find Aquarium Of Genoa. This stunning aquarium is a favorite among visitors.

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

Pisa 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 Pisa.

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.

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

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 6 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Pisa are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Knights' Square is must-visit public square and a great option for a daytime tour of the area. Continue your journey to Leaning Tower Of Pisa, a globally renowned monument, located just a leisurely stroll away.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Pisa. When you're ready, let your sightseeing route take you to the globally renowned Piazza Del Duomo, Pisa. If you’re looking for more, Pisa Cathedral is also a frequently visited attraction that is worthwhile a visit.

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 a true cultural experience.

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

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

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

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 5 nights.

Sistine Chapel makes a great addition to your morning plans.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Saint Peter's Square. Next, make your way to Vatican Museums to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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.

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.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

Raise your glass to another unforgettable day in Italy!

Day 8 of your road trip will take you to the best attractions Rome has to offer. Cherish the 4 nights you have left in the city and use the provided itinerary to discover what to see in Rome.

No visit to Rome is complete without Castel Sant'angelo. This impressive castle is one of the top attractions in the city. Proceed to Campo De' Fiori, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Navona. This timeless public square is a traveler-favorite. Not far away, you’ll find Pantheon, another key site on your sightseeing itinerary. Largo Di Torre Argentina is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

Make sure to reserve a table at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, a hidden gem nestled in Rome. 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 Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

Relax and look forward to more memorable moments to come!

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.

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.

Start your day at Archbasilica Of St. John Lateran. This breathtaking church is a well-known place to see in Rome. Then, wander over to Basilica Di Santa Maria Maggiore. If heritage-rich sites excite you, this church will be right up your alley. Nearby, you’ll also find Trevi Fountain. This enchanting monument is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Di Spagna is a globally renowned spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the enchanting Spanish Steps. Take a moment to appreciate the fascinating details of this widely recognized public square.

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.

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

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.

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

Day 10 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

Villa Borghese makes a great addition to your morning plans. This impressive park is a noteworthy place to see in Rome. Continue your discovery at Passeggiata Del Pincio, a stunning park with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Popolo. This impressive public square offers a noteworthy encounter with Rome. Next, make your way to Circus Maximus to add another highlight to your day. After that, visit Orange Garden, a well-known park 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 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.

Savor another day of unforgettable experiences in Italy!

On day 11 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 1 night.

Make a stop at Colosseum. This iconic archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Roman Forum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Capitoline Hill. Its visually striking features will captivate you. After the public square, continue your tour of the city with a visit to Capitoline Museums. Visitors usually appreciate the noteworthy features of this museum. Next up is Altare Della Patria, a highly recommended monument.

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 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 to another unforgettable day 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 place, which are Arezzo. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

Look forward to a unique sightseeing adventure at the locally appreciated San Francesco, Arezzo and allow yourself time to explore. Just a short distance away you'll find your next stop, Santa Maria Della Pieve, a visually striking church that draws visitors from far and near.

Continue your journey to Piazza Grande, one of the city’s most notable spots that you shouldn’t miss.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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

Day 13 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Florence.

Florence is brimming with adventures.

Awaiting your discovery is the astonishing Piazza Della Signoria, a history-steeped public square in Florence. Next, go to Palazzo Vecchio.

After visiting Piazza Della Signoria and Palazzo Vecchio, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Uffizi Gallery. This historic art gallery offers a unique experience. Ponte Vecchio is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazzale Michelangelo, one of the most history-steeped places to visit in Florence.

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 Florence's best restaurants.

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.

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.

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

Your itinerary for day 14 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Cathedral Of Santa Maria Del Fiore is perfect for a self-paced visit during the day. This romantic church is sure to impress. Next on your list is Galleria Dell'accademia, another must-visit landmark and notable art gallery renowned for its noteworthy features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Central Market. This photogenic food market is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Basilica Di Santa Maria Novella, Firenze (fi), a captivating church.

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.

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.

Begin your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at Lime Bar, where the evening is just getting started. In the same way, Macondo - Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Bologna. Bar Onda Marina By Night is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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