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.

Milan is brimming with adventures.

Start your day at Duomo Di Milano Museum. This inviting church is an iconic place to see in Milan. Then, wander over to Galleria Vittorio Emanuele Ii. If noteworthy sites excite you, this shopping mall will be right up your alley. Nearby, you’ll also find La Scala. This instagrammable opera house is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Sforzesco Castle Art Library is a spectacular spot in the city that will captivate you with its unique charm. When you’re done at the castle, don’t forget to check out the serene Parco Sempione. Take a moment to appreciate the fascinating details of this widely recognized park.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine.

Experience a taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and modern cuisine lovers seeking top-notch culinary experiences.

If you’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano 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!

On day 3 of your road trip, you'll get the chance to experience Milan and Sirmione. At the end of the day, you'll drive back to Milan, where you still have 1 night left to stay.

One of the most locally renowned attractions included on the itinerary is Pinacoteca Di Brera. This visually striking art gallery will help you start your sightseeing on top.

Throughout the day, make sure to take breaks to appreciate the surroundings.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Sirmione may take around 1 hour 41 min. Upon your arrival in Sirmione, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Beach Brema Sirmione is an often recommended beach we recommend visiting today. Discover its mesmerizing features before continuing your self-guided tour to Scaliger Castle, a romantic castle that’s well-regarded in the area.

Next, stop by Archaeological Site Of Grotte Di Catullo, a romantic archeological site.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Milan.

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

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu. You could also check for a table at Nero 9. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Milan tonight.

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.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Verona. When you’re not sightseeing, take time to relax at your chosen hotel in Venice, where you’ll be staying for 1 night.

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 Verona. Your travel time is around 2 hours 4 min.

Our first attraction recommendation in Verona is Castelvecchio Museum, a locally renowned museum that draws attention for its historic features. Spend some time soaking in the atmosphere before continuing to Castelvecchio Bridge, a history-steeped monument that stands out in the city.

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 Verona Arena, a globally renowned stadium that offers a unique experience. Be sure to also explore Piazza Delle Erbe, a nearby public square, highly recommended by other travelers.

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

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

Get ready for an unforgettable culinary journey in Venice by reserving a table at Local. Renowned as a 1-star Michelin restaurant, it offers an exceptional contemporary menu. For a different taste experience, head to Wistèria, recognized for its delicious contemporary and venetian dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Quadri, a local favorite known for its delightful modern cuisine in Venice. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for modern foodies seeking culinary excellence.

Extend your evening after a delightful meal by visiting Al Parlamento, which offers the perfect atmosphere for a night out. Moreover, The Caffe Rosso is another popular option for a drink or two. Likewise, Adagio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Venice. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Rialto Bridge is must-visit historical landmark and a great option for a daytime tour of the area. Continue your journey to Piazza San Marco, a timeless public square, located just a leisurely stroll away. Next, head to St Mark's Basilica, a romantic church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Venice. When you're ready, let your sightseeing route take you to the interesting Doge's Palace. If you’re looking for more, Bridge Of Sighs is also a popular attraction that is worthwhile a visit.

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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Bologna. Enjoy a relaxing evening as you savor delicious local cuisine.

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Al Bricco D'oro, known for its inviting atmosphere. Bar Freud E Squisito is another great option if you’re looking for a place to get the night started. Similarly, Osteria Del Sole provides a great setting to enjoy the night away.

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

Dive into day 6 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Bologna and Siena. At the end of the day, you’ll unwind at one of the finest accommodations in Arezzo, where you'll spend 1 night.

Experience Two Towers, a popular monument in the city. Then, head to Piazza Maggiore and soak in the ambiance of this romantic public square.

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 2 hours 11 min. When you arrive in Siena, it's time to take a break from the road.

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 picture-perfect monument.

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

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

Experience a symphony of flavors at Octavin in Arezzo by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Octavin delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. Or, if you're feeling adventurous, why not try La Clandestina? It's another excellent option with a diverse menu.

If you’re not ready to end the night just yet, Liquid Bar offers a perfect venue to relax and savor a drink.

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

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 2 hours 32 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Vatican Museums, an iconic art museum in Vatican City. This widely recognized chapel is a top recommendation in the area.

When you’re ready to explore more, Saint Peter's Square is an excellent choice. Next, continue your sightseeing at the iconic St. Peter's Basilica and discover what makes this major basilica unique.

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

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

Have a memorable dining experience in Rome by booking a table at La Pergola, a 3-star Michelin restaurant presenting an exceptional mediterranean and contemporary menu. For a different culinary experience in Rome, Il Pagliaccio shines as one of the top destinations, known for its delicious creative and innovative cuisine. This 2-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Enoteca La Torre is known as a top local spot in Rome for its delicious mediterranean and creative cuisine. This 2-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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.

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

Let Foro Italico set the tone for the day. Spend some time admiring this photogenic sports complex before continuing your journey. Piazza Del Popolo is your next stop. This top-rated public square is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Villa Borghese. This standout park is a sight to behold. To round off your sightseeing experience, visit Basilica Di Santa Maria Maggiore and 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.

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 RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

Say good night to Rome and look forward to another great day of your road trip 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.

Colosseum is must-visit archeological site and a great option for a daytime tour of the area. Continue your journey to Roman Forum, a wondrous archeological site, located just a leisurely stroll away. Next, head to Capitoline Hill, a romantic 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 popular Altare Della Patria. 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 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 Rome's best restaurants.

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

Raise your glass to another unforgettable day 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.

Look forward to a unique sightseeing adventure at the interesting Orange Garden and allow yourself time to explore. Just a short distance away you'll find your next stop, Circus Maximus, a stunning archeological site that draws visitors from far and near.

Continue your journey to Campo De' Fiori, one of the city’s most astonishing spots that you shouldn’t miss. Another great site to visit is the iconic Piazza Navona. When you're finished at the public square, Castel Sant'angelo awaits your visit. This castle is a history-steeped 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.

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 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.

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

Catch Pantheon before the crowds roll in. This photogenic monument is sure to ignite your curiosity. Next, dive into the grand features of Trevi Fountain, a must-visit monument 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 Piazza Di Spagna, a globally renowned public square. For a change of scene, check out Spanish Steps, known for its visually striking features. We also recommend visiting Auditorium Parco Della Musica. This concert hall is a must for anyone looking to experience the city to the fullest.

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

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

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

On day 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.

To truly experience Florence, make sure to drop by Basilica Di Santa Maria Novella, Firenze (fi). This well-known church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Central Market, one of the city’s best highlights.

Next, check out Cathedral Of Santa Maria Del Fiore, one of the most extraordinary places to see in Florence. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Galleria Dell'accademia. Wander around and soak in the eye-catching atmosphere this art gallery offers.

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 Florence, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

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.

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

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

Enjoy all that Piazza Della Signoria has to offer. This is an astonishing public square you should not miss. Another must-see is Ponte Vecchio, a timeless historical landmark in Florence.

When you’re ready for the next sight, head to Uffizi Gallery. From there, take a leisurely stroll to Basilica Of Santa Croce In Florence, another of the city’s captivating attractions. We recommend continuing your self-guided tour at Piazzale Michelangelo, an enchanting place of interest in the city.

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

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

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.

After your meal, keep the night alive at a bar like Jeffer Cocktails & Friends, known for its lively atmosphere. Le Parisien Wine Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Las Volta Cocktailbar offers an excellent atmosphere for those looking to amp up the evening.

Relax and look forward to more memorable moments to come!

Your itinerary for day 14 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Genoa. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

Make a stop at Leaning Tower Of Pisa. This wondrous monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Duomo, Pisa located in Pisa for another exciting encounter.

Next, immerse yourself in the setting of Pisa Cathedral. Its UNESCO world heritage-listed features will captivate you.

When you’re ready to jump back into the car and say goodbye to Pisa, you’ll hit the road in the direction of Genoa. This drive usually takes around 1 hour 43 min.

Spiaggia Pubblica Di Priaruggia is a curiosity-inducing beach we recommend visiting today. Discover its romantic features before continuing your self-guided tour.

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

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

Don’t miss out on dining at Ristorante la Brisa, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Pasticceria San Carlo, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Round off your dining experience by visiting Qc Termemilano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yguana Cafè, a bar catering to every mood and preference.

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