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

Day 2 of your road trip across Italy promises a magnificent time exploring Milan. You have 2 nights left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most timeless attractions included on the itinerary is Duomo Di Milano Museum. This visually striking church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Vittorio Emanuele Ii and learn what makes this detailed shopping mall unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the well-known La Scala. After exploring the opera house, head to Sforzesco Castle Art Library. This spectacular castle is a highlight in Milan. As your day continues, stop by Parco Sempione, known for its serene features.

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 Milan. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 3 of your road trip, you’ll start and end your day in Milan, where you'll stay for 1 night more.

Today’s route brings fun adventures, picturesque spots, and history-rich sites. The first attraction of today is Pinacoteca Di Brera. This interesting art gallery is a photogenic place to see in Milan. Continue your discovery at Beach Brema Sirmione, an eye-catching beach with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Scaliger Castle. This astonishing castle offers a history-steeped encounter with Milan. Next, make your way to Archaeological Site Of Grotte Di Catullo 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 Milan.

When you’re done exploring for the day, you’ll return to Milan and your accommodation.

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

Make sure to reserve a table at Bice Restaurant, 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 Alto Ristorante, 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 Nero 9, 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 your meal, keep the night alive at a bar like Bhangrabar, known for its lively atmosphere. Rufus Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ostello Bello Grande 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 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Verona. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 1 night.

Milan is home to plenty of attractions that offer fun adventures, breathtaking views, and photo-friendly spots! Start at Castelvecchio Museum, a well-known museum that is worthwhile a visit in the city. Nearby, you’ll find Castelvecchio Bridge, enchanting visitors with its enchanting appeal. Continue your exploration at Verona Arena. This stadium is one of the city’s most world-famous spots.

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

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

As you explore more of Venice, 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 memorable dining experience in Venice by booking a table at Local, renowned as a 1-star Michelin restaurant presenting an exceptional contemporary menu. For a different culinary experience in Venice, Wistèria shines as one of the top destinations, known for its delicious contemporary and venetian cuisine. This 1-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Quadri is known as a top local spot for its delicious modern cuisine in Venice. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Venice. 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.

Bring your curiosity for today’s adventure around Venice. Some of the city’s most loved attractions await! Rialto Bridge is the perfect place to start. This historical landmark is one of the most timeless places to visit in Venice. Next, head to Piazza San Marco, a globally renowned public square, known for its enchanting features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to St Mark's Basilica. This UNESCO world heritage-designated church is a highly recommended experience. Nearby, you'll also find Doge's Palace and Bridge Of Sighs. Visit these for an interesting touch to your journey.

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

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.

Let the evening flow smoothly from dinner to drinks at Bar Al Bricco D'oro, a top-rated bar in the area. For other recommendations, Bar Freud E Squisito provides a perfect setting for rounding out your night with style and great drinks. Likewise, Osteria Del Sole offers a memorable night with diverse drink options and excellent service.

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

On day 6 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 Bologna and Siena. In the evening, you’ll end up in Arezzo, where you will stay for 1 night.

A blend of fun adventures, breathtaking views, and picturesque spots await you in Bologna on today’s itinerary. First up is the well-known monument, Two Towers. Afterward, continue to Piazza Maggiore, a public square 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 Siena Cathedral. This interesting church is an essential stop. Following that, head to Piazza Del Campo, another must-visit site that will enhance your experience. Don’t forget to stop by Tower Of Mangia, a worthwhile monument in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Arezzo. Check in and spend some time relaxing 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 Arezzo. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Start your culinary exploration in Arezzo by securing a reservation at Octavin. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine. Immerse yourself in the culinary delights of La Clandestina, a popular restaurant in Arezzo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

Keep the evening going at Liquid Bar, a great choice for enjoying the after-dinner hours with a drink.

Raise your glass to another unforgettable day in Italy!

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Vatican City, 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 Rome. You’ll stay here for 4 nights.

Start your day at Vatican Museums. Then, wander over to Sistine Chapel. Nearby, you’ll also find Saint Peter's Square.

Arezzo offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, St. Peter's Basilica is a timeless spot in the city that will captivate you with its unique charm.

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

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

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 8 of your road trip will take you to the best attractions Rome has to offer. Cherish the 3 nights you have left in Rome by discovering the best things there are to see and do in the city.

Prepare for a day full of family-friendly attractions, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Foro Italico. This well-known sports complex is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Popolo, one of the city’s best highlights.

Next, check out Villa Borghese, one of the most extraordinary places to see in Rome. This park is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Basilica Di Santa Maria Maggiore. Wander around and soak in the culturally significant atmosphere this church offers. Then, head to Archbasilica Of St. John Lateran, a top-rated church 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 Rome's best restaurants.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

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

Day 9 offers a multitude of experiences. You will stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Rome covers several incredible sights, including an archeological site, a public square, and a monument. Start your adventure at Colosseum. This timeless archeological site is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the breathtaking wonders of Roman Forum, a must-see archeological site 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 Capitoline Hill. This captivating public square offers an enriching experience. For a change of pace, head to Altare Della Patria, where you can take in culturally significant 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.

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

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

Keep the excitement of the evening going by visiting a bar or two. The Apartment Bar Roma is an excellent place to start. You could also check out Hotel Hassler Roma, offering a different kind of charm.

Raise your glass to another unforgettable day in Italy!

On day 10 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.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a park, an archeological site, a public square, a castle and much more! Begin your adventure at Orange Garden. This is a locally renowned park you should not miss. Another must-see is Circus Maximus, a well-known archeological site in Rome.

When you’re ready for the next sight, head to Campo De' Fiori. From there, take a leisurely stroll to Piazza Navona, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Castel Sant'angelo, an enchanting 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.

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

Enjoy a delicious meal at Sofitel Roma Villa Borghese, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Centro, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

Embark on another extraordinary experience on day 11 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. 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.

Today, you'll explore some of the most beautiful places in Rome, including a monument, a public square, and a concert hall. Start your day with a visit to Pantheon. This timeless monument is a must-visit in the city. When you’re ready for your next discovery, continue to Trevi Fountain, which may be one of the most romantic 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 Piazza Di Spagna, a globally renowned public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Spanish Steps and Auditorium Parco Della Musica.

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.

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.

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean 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 Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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 12 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.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Basilica Di Santa Maria Novella, Firenze (fi). This well-known church is one of the top attractions in the city. Proceed to Central Market, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Cathedral Of Santa Maria Del Fiore. This top-rated church is a traveler-favorite. Not far away, you’ll find Galleria Dell'accademia, another key site on your sightseeing itinerary.

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 Florence, 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 Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

On day 13 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Florence. Your adventure starts at Piazza Della Signoria, an astonishing local hot spot. Another notable attraction to explore is Ponte Vecchio. This world-famous historical landmark is known for its history-steeped appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Uffizi Gallery. This picture-perfect art gallery offers a fascinating experience that many visitors find memorable. Basilica Of Santa Croce In Florence is also worth visiting, along with Piazzale Michelangelo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

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

Treat yourself to a wonderful meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining spot in Pisa. If you're in the mood for something new, try il Mercante, another premier location with a delectable menu. You might also want to book a table at La Ghiotteria. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

Explore the vibrant nightlife at Jeffer Cocktails & Friends after your meal, a hub for lively evenings and memorable moments. Or, head to Le Parisien Wine Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Las Volta Cocktailbar is perfect for those looking to extend their night with a touch of local flavor.

Head back to your accommodation in Pisa and get some rest in preparation for another magical day of your road trip 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 2 vibrant destinations - Pisa and Genoa. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 1 night here for some well-deserved relaxation.

Brace yourself for today’s incredible lineup of attractions in Pisa, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Leaning Tower Of Pisa, an iconic monument in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this culturally significant public square.

There are many interesting places to see in Pisa, and when you are ready for more, go to Pisa Cathedral. This is one of the city’s most increasingly popular stunning spots of interest. After exploring the church, visit the worthwhile Spiaggia Pubblica Di Priaruggia.

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

Enjoy a lovely meal at Ristorante la Brisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Pasticceria San Carlo is another top choice with a popular menu. You could also check for a table at UNAHOTELS Cusani Milano. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

After enjoying a fulfilling meal, continue your evening at Qc Termemilano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yguana Cafè offers a welcoming atmosphere for easing into the nightlife.

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