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

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 3 nights.

Bologna is brimming with adventures. Today’s wonderful stops include a monument, a park, a public square, a museum and much more! Begin your sightseeing adventure at the well-known Two Towers and allow yourself time to explore. Just a short distance away you'll find your next stop, Villa Ghigi, a romantic park that draws visitors from far and near.

Continue your journey to Piazza Santo Stefano, one of the city’s most often recommended spots that you shouldn’t miss. Another great site to visit is the curiosity-inducing International Museum And Library Of Music.

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

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 and reflect on the day'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 discerning italian contemporary and modern foodies seeking culinary excellence.

Keep the evening going at Nottingham Forest, a great choice for enjoying the after-dinner hours with a drink. You could also go to Armani/bamboo Bar, which offers a similarly pleasant setting and great drinks. Another option is Mag Cafe, which provides an inviting environment for unwinding after a busy day out.

Relax and recharge in preparation for another adventurous 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.

Immerse yourself in Milan’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Gae Aulenti. This awe-inspiring public square is sure to ignite your curiosity. Next, dive into the history-steeped features of Duomo Di Milano Museum, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Royal Palace Of Milan, a notable palace. For a change of scene, check out Galleria Vittorio Emanuele Ii, known for its romantic features. We also recommend visiting La Scala. This opera house is a must for anyone looking to experience the city to the fullest.

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 Milan's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a wonderful meal at Dessert Bar Milano, a top-rated dining spot in Milan. If you're in the mood for something new, try Radisson Blu Hotel Milan, another premier location with a delectable menu. You might also want to book a table at Ristorante Qui Si Mangia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

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!

On day 4 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 1 night and discover all the best things to see and do in the area.

Today, you'll explore some of the most beautiful places in Milan, including a church, an art gallery, a castle, a park, a monument and much more! Start your day with a visit to Santa Maria Delle Grazie Church. This captivating church is a must-visit in the city. When you’re ready for your next discovery, continue to Pinacoteca Di Brera, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Milan 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 Sforzesco Castle Art Library, a spectacular castle in the city. If you’re up for more discoveries, don’t forget to reserve some time for Parco Sempione and Arch Of Peace.

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

As you explore more of Milan, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Savor the flavors at Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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

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

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

Brace yourself for today’s incredible lineup of attractions in Milan, featuring fun adventures, picturesque spots, and history-rich sites. Start at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a locally renowned museum in the city.

There are many interesting places to see in Milan, and when you are ready for more, go to Aquarium Of Genoa. This is one of the city’s most famous breathtaking spots of interest.

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

As you explore more of Pisa, 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.

Have a fantastic dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a highly recommended choice for tonight's dinner. If you're looking to mix things up, il Mercante offers an enticing alternative with its varied menu. Additionally, La Ghiotteria is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Jeffer Cocktails & Friends, a well-loved spot among locals and tourists. Or, head to Le Parisien Wine Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Las Volta Cocktailbar, another top-rated place in the area.

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

Begin your adventure at Knights' Square. This is an underrated public square you should not miss. Another must-see is Leaning Tower Of Pisa, an iconic monument in Pisa.

When you’re ready for the next sight, head to Angelo Caduto. From there, take a leisurely stroll to Piazza Del Duomo, Pisa, another of the city’s globally renowned attractions. We recommend continuing your self-guided tour at Pisa Cathedral, a stunning place of interest in the city.

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

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

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.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

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

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Vatican City. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 5 nights here for some well-deserved relaxation.

Start at Sistine Chapel, an extraordinary chapel that is worthwhile a visit in the city. Continue your exploration at Saint Peter's Square. This square is one of the city’s most well-known spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Vatican Museums.

At the end of the day, you will drive to Rome, 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 Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of mediterranean and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative and innovative 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 Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean and creative menu. With a 2-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 Rome.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 8 of your road trip across Italy promises a magnificent time exploring Rome. You have 4 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s agenda in Rome includes a castle, a public square, a monument, an archeological site and much more! Castel Sant'angelo is must-visit castle and a great starting point for the day. Next, continue your journey to Campo De' Fiori, an astonishing public square, located just a leisurely stroll away. Next, head to Piazza Navona, a masterful public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the wondrous Pantheon. If you’re looking for more, Largo Di Torre Argentina is also a captivating attraction that is worthwhile a visit.

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.

Don’t miss out on dining 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 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.

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

Day 9 offers a multitude of experiences. You will stay in Rome for 3 nights more, offering you enough time to explore at a relaxed pace.

Get ready for a day filled with family-friendly attractions, breathtaking views, and photo-friendly spots in the charming city of Rome. Your adventure starts at Archbasilica Of St. John Lateran, a popular local hot spot. Another notable attraction to explore is Basilica Di Santa Maria Maggiore. This well-known church is known for its picture-perfect 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 Trevi Fountain. This history-steeped monument offers a fascinating experience that many visitors find memorable. Piazza Di Spagna is also worth visiting, along with Spanish Steps. 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.

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 delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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.

Savor another day of unforgettable experiences in Italy!

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a park, a public square, and an archeological site. Begin your adventure at Villa Borghese. This is an impressive park you should not miss. Another must-see is Passeggiata Del Pincio, a locally renowned 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 locally renowned 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 activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Enjoy a lovely dining experience at Sofitel Roma Villa Borghese, 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 Centro, 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 Tema. It’s yet another ideal choice to enhance your time in Rome tonight.

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

On day 11 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Rome is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and picturesque spots! Start at Colosseum, an iconic archeological site that is worthwhile a visit in the city. Nearby, you’ll find Roman Forum, enchanting visitors with its picture-perfect appeal. Continue your exploration at Capitoline Hill. This public square is one of the city’s most notable 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 Capitoline Museums. After exploring the museum, head to the interesting 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.

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.

Enjoy a delicious meal 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.

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

On day 12 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 Arezzo. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to San Francesco, Arezzo. This underrated church provides an insightful glimpse into the city's identity. Next, discover Santa Maria Della Pieve, a visually striking church, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Grande, a popular public square.

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

As 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.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

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

Day 13 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Start by visiting Piazza Della Signoria, a prime spot to begin your journey. This visually striking public square is sure to impress. Next on your list is Palazzo Vecchio, another must-visit landmark and captivating palace renowned for its culturally significant 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 Uffizi Gallery. This picture-perfect art gallery is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Ponte Vecchio, a wondrous historical landmark. Nearby, you'll also find Piazzale Michelangelo, ready to add charm to your journey.

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 Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

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

Embark on another extraordinary experience on day 14 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

Savor the day by visiting some of the best places to see in Florence, including a church, an art gallery, and a food market. Start your adventure at Cathedral Of Santa Maria Del Fiore. This impressive church is a must-visit for travelers looking for a unique holiday experience. Make your way to Galleria Dell'accademia located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Central Market. Its instagrammable features will captivate you. After the food market, continue your tour of the city with a visit to Basilica Di Santa Maria Novella, Firenze (fi). Visitors usually appreciate the enchanting features of this church.

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

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

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.

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!