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 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 3 nights here for some well-deserved relaxation.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the captivating Two Towers, a stunning monument in Bologna. Next, go to Villa Ghigi.

After visiting Two Towers and Villa Ghigi, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Piazza Santo Stefano. This inviting public square offers a unique experience. International Museum And Library Of Music is another noteworthy attraction worthwhile a visit.

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

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

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

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.

Raise your glass to another unforgettable day 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.

Get ready for a day filled with family-friendly attractions, scenic views, and picturesque spots in the charming city of Milan. Your adventure starts at Piazza Gae Aulenti, a captivating local hot spot. Another notable attraction to explore is Duomo Di Milano Museum. This timeless church is known for its instagrammable appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Royal Palace Of Milan. This respected palace offers a fascinating experience that many visitors find memorable. Galleria Vittorio Emanuele Ii is also worth visiting, along with La Scala. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Milan. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Dessert Bar Milano, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Radisson Blu Hotel Milan, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Qui Si Mangia, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

Day 4 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Prepare for a day full of fun adventures, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Santa Maria Delle Grazie Church. This locally renowned church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Pinacoteca Di Brera, one of the city’s best highlights.

Next, check out Sforzesco Castle Art Library, one of the most top-rated places to see in Milan. This castle is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Parco Sempione. Wander around and soak in the eye-catching atmosphere this park offers. Then, head to Arch Of Peace, a top-rated monument that adds another dimension to your 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.

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

Have a fantastic dining experience at Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

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

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

On day 5 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 Milan and Genoa. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most locally renowned attractions included on the itinerary is Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This historic museum will help you start your sightseeing on top.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the extraordinary Aquarium Of Genoa.

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

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.

Treat yourself to a delightful dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try il Mercante? It's another excellent option with a diverse menu. Consider reserving a table at La Ghiotteria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Jeffer Cocktails & Friends stands out as an excellent choice for a post-dinner cocktail. Alternatively, Le Parisien Wine Bar offers an ideal atmosphere to enjoy the pleasures of the night. Las Volta Cocktailbar is also a great option that provides a perfect setting for a relaxing evening.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Pisa, 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 Siena. You’ll stay here for 1 night.

Start your day with a visit to Knights' Square. This worthwhile public square is a must-visit in the city. When you’re ready for your next discovery, continue to Leaning Tower Of Pisa, which may be one of the most detailed places you will experience today.

One of the best things about exploring Pisa on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Angelo Caduto, an underrated point of interest in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Del Duomo, Pisa and Pisa Cathedral.

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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying 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 world-famous spot in the city that will captivate you with its unique charm.

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

As dinnertime approaches, it's time to head out for a bite to eat in Rome. 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.

Discover the culinary delights of Rome by securing a reservation at La Pergola. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of mediterranean and contemporary cuisine. For an alternative dining experience, try Il Pagliaccio, renowned for its delicious creative and innovative dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Enoteca La Torre, a highly recommended local eatery celebrated for its mouthwatering mediterranean and creative menu. With its 2-star Michelin recognition, it offers an unforgettable dining adventure.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 8 offers a multitude of experiences. You will stay in Rome for 4 nights more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Rome covers several incredible sights, including a castle, a public square, a monument, an archeological site and much more! Start your adventure at Castel Sant'angelo. This impressive castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Campo De' Fiori, a must-see public square 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 Piazza Navona. This globally renowned public square offers an enriching experience. For a change of pace, head to Pantheon, where you can take in heritage-rich features. Conclude your self-guided sightseeing tour with a visit to Largo Di Torre Argentina. 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 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.

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.

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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

On day 9 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 3 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 Archbasilica Of St. John Lateran. This culturally significant church is a highlight of any visit in the city. Then, enjoy Basilica Di Santa Maria Maggiore, another UNESCO world heritage-listed attraction that never fails to captivate visitors. Next, head over to Trevi Fountain, 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 Piazza Di Spagna. This visually striking public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Spanish Steps, a spectacular public square, 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.

Make sure to reserve a table at Hotel de Russie, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Taverna Italiana, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of The Parrot Bar, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

Relax and recharge in preparation for another adventurous day 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.

A blend of family-friendly attractions, romantic experiences, and natural wonders await you in Rome on today’s itinerary. First up is the extraordinary park, Villa Borghese. Afterward, continue to Passeggiata Del Pincio, a park 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 Del Popolo. This extraordinary public square is an essential stop. Following that, head to Circus Maximus, another must-visit site that will enhance your experience. Don’t forget to stop by Orange Garden, a well-known park 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 Rome, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

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

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

Day 11 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Today, you'll explore some of the most beautiful places in Rome, including an archeological site, a public square, a museum, a monument and much more! Start your day with a visit to Colosseum. This timeless archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Roman Forum, which may be one of the most historic places you will experience today.

One of the best things about exploring Rome on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Capitoline Hill, a notable public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Capitoline Museums and Altare Della Patria.

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.

Dine in style at Ristorante Va. Do. , a top recommendation for dinner tonight. Or, for a change of pace, Giulia Restaurant boasts a menu that's sure to impress. Also, be sure to check out L'Archeologia. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

Embark on another extraordinary experience on day 12 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Arezzo. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Rome is brimming with adventures. Today’s wonderful stops include a church and a public square. Begin your sightseeing adventure at the underrated 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 romantic church that draws visitors from far and near.

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

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

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

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 13 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Get ready to discover some of the most iconic wonders in Florence, including a public square, a palace, an art gallery, a historical landmark, an observation deck and much more! Start your day at Piazza Della Signoria. This enchanting public square is a widely recognized place to see in Florence. Then, wander over to Palazzo Vecchio. If history-steeped sites excite you, this palace will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This respected art gallery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Ponte Vecchio is a wondrous spot in the city that will captivate you with its unique charm. When you’re done at the historical landmark, don’t forget to check out the romantic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this famous observation deck.

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

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day 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 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Cathedral Of Santa Maria Del Fiore. This romantic church is a highlight of any visit in the city. Then, enjoy Galleria Dell'accademia, another noteworthy attraction that never fails to captivate visitors. Next, head over to Central Market, one of the city’s most well-known attractions, known for its photogenic features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Di Santa Maria Novella, Firenze (fi). This enchanting church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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 you explore more of Bologna, 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.

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.

After your meal, keep the night alive at a bar like Lime Bar, known for its lively atmosphere. Macondo - Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Onda Marina By Night offers an excellent atmosphere for those looking to amp up the evening.

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