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

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

Look forward to a unique sightseeing adventure at the timeless Duomo Di Milano Museum and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Vittorio Emanuele Ii, a history-steeped shopping mall that draws visitors from far and near.

Continue your journey to La Scala, one of the city’s most well-known spots that you shouldn’t miss. Another great site to visit is the famous Sforzesco Castle Art Library. When you're finished at the castle, Parco Sempione awaits your visit. This park is an eye-catching highlight on today's itinerary.

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 an outstanding dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an exceptional creative menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Seta by Antonio Guida, known for its delicious international and contemporary cuisine. Another highly-recommended place to eat in Milan is Il Luogo Aimo e Nadia, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious italian contemporary and modern menu.

After enjoying a fulfilling meal, continue your evening at Kilburn Cocktail Bar Milano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Frida offers a welcoming atmosphere for easing into the nightlife. Similarly, The Friends Pub Milano provides an excellent environment for a relaxed and enjoyable evening.

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

Wake up to day 3 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Milan and Sirmione. With 1 night to stay in Milan, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Let Pinacoteca Di Brera set the tone for the day. Spend some time admiring this photogenic art gallery before continuing your journey.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Sirmione. Your travel time is around 1 hour 41 min.

Savor the day by heading to Beach Brema Sirmione, a beloved beach that draws visitors from near and far. When you're done, continue to Scaliger Castle, where you can soak in the grand surroundings.

Next, explore Archaeological Site Of Grotte Di Catullo, yet another notable place to see in the area.

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

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.

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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

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

Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 1 night.

Continue your road trip and head to your next destination, Verona. This car ride takes around 2 hours 4 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castelvecchio Museum, a well-known museum that everyone visiting Verona should see. Next, head to Castelvecchio Bridge. This romantic monument is one of the most well-known attractions in the region.

If you're keen to see more, don’t miss out on Verona Arena, an enchanting stadium popular among locals as well as travelers. Piazza Delle Erbe is an excellent attraction to visit next. Spend some time learning more about this well-known public square before you continue your journey.

At the end of the day, you will drive to Venice, 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 Venice's most popular restaurants, and connect with friendly locals for a true cultural experience.

Treat yourself to an extraordinary dining experience at Local, a 1-star Michelin restaurant offering an incredible contemporary menu. Alternatively, if your taste buds call for something different, Wistèria is one of the best restaurants for contemporary and venetian cuisine in Venice. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Quadri. As a top-rated establishment with 1 Michelin star, it is an ideal choice for modern cuisine in the city.

Explore the vibrant nightlife at Al Parlamento after your meal, a hub for lively evenings and memorable moments. Or, head to The Caffe Rosso for a great selection of flavorful drinks and a charming setting. Furthermore, Adagio is perfect for those looking to extend their night with a touch of local flavor.

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

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

Rialto Bridge is perfect for a self-paced visit during the day. This history-steeped historical landmark is sure to impress. Next on your list is Piazza San Marco, another must-visit landmark and wondrous public square renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of Venice by sampling some local delicacies. When you’re ready for more sightseeing, head to St Mark's Basilica. This enchanting church is an essential place to visit for anyone looking for the full Venice experience. We also recommend visiting Doge's Palace, an interesting palace. Nearby, you'll also find Bridge Of Sighs, ready to add charm to your journey.

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

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.

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 savoring a delicious meal, step into the vibrant nightlife at Bar Al Bricco D'oro, where the evening is just getting started. In the same way, Bar Freud E Squisito offers a unique charm perfect for experiencing the local bar scene in Bologna. Osteria Del Sole 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!

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Bologna and Siena. When you’re not sightseeing, take time to relax at your chosen hotel in Arezzo, where you’ll be staying for 1 night.

Start your day at Two Towers. This historic monument is a locally renowned place to see in Bologna. Then, wander over to Piazza Maggiore. If visually striking sites excite you, this public square will be right up your alley.

Embrace the thrill of the open road as you wave goodbye to Bologna and set your GPS to Siena. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 11 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Set out on a self-guided sightseeing tour at Siena Cathedral and explore the romantic features. Next, make your way to Piazza Del Campo, another highlight in Siena. When you’re done exploring the public square, continue to Tower Of Mangia, a historic monument.

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

Arezzo 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 Arezzo.

Dive into a culinary adventure like no other in Arezzo by booking a table at Octavin. This popular restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine. If you're in the mood to try something new, consider La Clandestina, another top spot with a mouthwatering menu.

To truly maximize your evening out, consider visiting Liquid Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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.

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 place, which are Vatican City. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 4 nights.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Vatican City, Vatican City. Witness the landscapes transform as you cross the border to Vatican City. This drive usually takes around 2 hours 32 min.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Saint Peter's Square, a notable square that offers a unique experience. Be sure to also explore St. Peter's Basilica, a nearby major basilica, highly recommended by other travelers.

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

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.

Extend your evening after a delightful meal by visiting La Botticella Of Poggi Giovanni, which offers the perfect atmosphere for a night out. Moreover, Almalu Trastevere is another popular option for a drink or two. Likewise, Bar Viminale Di Pepi Maurilio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 the city and use the provided itinerary to discover what to see in Rome.

Rome is brimming with adventures.

Make time for Foro Italico, a captivating sports complex that is worthwhile a visit in the city. Nearby, you’ll find Piazza Del Popolo, enchanting visitors with its history-steeped appeal. Continue your exploration at Villa Borghese. This park is one of the city’s most spectacular 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 Basilica Di Santa Maria Maggiore. After exploring the church, head to the captivating Archbasilica Of St. John Lateran.

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

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

Enjoy a delicious meal 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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Sant' Eustachio Caffè, a well-loved spot among locals and tourists. Or, head to Yellowsquare Rome. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Caffè Portofino, another top-rated place in the area.

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

Day 9 offers an itinerary packed with the best things to see in Milan. You’ll stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

To truly experience Rome, make sure to drop by Colosseum. This globally renowned archeological site is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Roman Forum, one of the city’s best highlights.

Next, check out Capitoline Hill, one of the most locally renowned places to see in Rome. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Altare Della Patria. Wander around and soak in the awe-inspiring atmosphere this monument offers. Then, head to Largo Di Torre Argentina, a top-rated archeological site that adds another dimension to your day.

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

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.

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.

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.

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

Day 10 of your road trip across Italy promises a magnificent time exploring what to see in Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Visiting Orange Garden is always a good idea. This captivating park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Circus Maximus, 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 Campo De' Fiori. This top-rated public square offers an enriching experience. For a change of pace, head to Piazza Navona, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Castel Sant'angelo 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 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.

Make sure to reserve a table at Sofitel Roma Villa Borghese, 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 Centro, 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 Ristorante Tema, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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 11 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

One of the most globally renowned attractions included on the itinerary is Pantheon. This respected monument will help you start your sightseeing on top. Then, take a leisurely stroll to Trevi Fountain and learn what makes this detailed monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the globally renowned Piazza Di Spagna. After exploring the public square, head to Spanish Steps. This widely recognized public square is a highlight in Rome. As your day continues, stop by Auditorium Parco Della Musica, known for its eye-catching features.

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

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.

Start your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it guarantees an exceptional 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 sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 12 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 1 night.

Experience Basilica Di Santa Maria Novella, Firenze (fi), a well-known church in the city. Then, head to Central Market and soak in the ambiance of this visually striking food market.

There are many interesting places to see in Florence, and when you are ready for more, go to Cathedral Of Santa Maria Del Fiore. This is one of the city’s most impressive majestic spots of interest. After exploring the church, visit the captivating Galleria Dell'accademia.

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

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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.

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!

Your itinerary for day 13 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 Pisa, where you'll spend 1 night.

Visiting Piazza Della Signoria is always a good idea. This astonishing public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Ponte Vecchio, a must-see historical landmark 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 Uffizi Gallery. This impressive art gallery offers an enriching experience. For a change of pace, head to Basilica Of Santa Croce In Florence, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo These sights offer a fulfilling end to a perfect day.

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.

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

Enjoy a delicious meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Let the evening flow smoothly from dinner to drinks at Jeffer Cocktails & Friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta Cocktailbar offers a memorable night with diverse drink options and excellent service.

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

Dive into day 14 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Pisa and Genoa. At the end of the day, you’ll unwind at one of the finest accommodations in Milan, where you'll spend 1 night.

Your adventure in Pisa is only getting started when you visit Leaning Tower Of Pisa, an iconic local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This globally renowned public square is known for its noteworthy appeal.

After soaking in the highlights of these sights, take some time to wander Pisa's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Pisa Cathedral. This majestic church offers a fascinating experience that many visitors find memorable.

Genoa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 1 hour 43 min. Genoa welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Spiaggia Pubblica Di Priaruggia, a frequently visited beach that everyone visiting Genoa should see.

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.

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

Make sure to reserve a table at Ristorante la Brisa, 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 Pasticceria San Carlo, 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 UNAHOTELS Cusani Milano, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Qc Termemilano stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yguana Cafè offers an ideal atmosphere to enjoy the pleasures of the night.

Savor another day of unforgettable experiences in Italy!