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

On day 2 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 2 nights and discover all the best things to see and do in the area.

Start by visiting Duomo Di Milano Museum, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Galleria Vittorio Emanuele Ii, another must-visit landmark and spectacular shopping mall renowned for its noteworthy features.

While exploring and sightseeing, take time to savor the ambiance of Milan by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to La Scala. This historic opera house is a remarkable attraction that offers a unique experience. Sforzesco Castle Art Library also adds charm to your journey, and Parco Sempione wraps up your day with its mesmerizing appeal.

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.

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and modern cuisine in the city.

Keep the evening going at Kilburn Cocktail Bar Milano, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Frida, which offers a similarly pleasant setting and great drinks. Another option is The Friends Pub Milano, which provides an inviting environment for unwinding after a busy day out.

Relax and recharge in preparation for another adventurous day 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 itinerary in Milan covers several incredible sights, including an art gallery, a beach, a castle, an archeological site and much more! Start your adventure at Pinacoteca Di Brera. This popular art gallery is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the instagrammable wonders of Beach Brema Sirmione, a must-see beach 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 Scaliger Castle. This widely recognized castle offers an enriching experience. For a change of pace, head to Archaeological Site Of Grotte Di Catullo, where you can take in romantic features.

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

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 delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After enjoying a fulfilling meal, continue your evening at Bhangrabar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Rufus Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Ostello Bello Grande provides an excellent environment for a relaxed and enjoyable 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, Verona. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Castelvecchio Museum is the first of them. Spend some time admiring this historic museum before continuing your journey. Castelvecchio Bridge is your next stop. This locally renowned monument is one of the best-rated sights in Milan.

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 Verona Arena. This grand stadium is a sight to behold. To round off your sightseeing experience, visit Piazza Delle Erbe.

When you’re done exploring for the day, you’ll drive to your hotel in Venice. Check in and spend some time relaxing 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 discerning 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.

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

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Venice, 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 Bologna. You’ll stay here for 1 night.

Today, you'll explore some of the most beautiful places in Venice, including a historical landmark, a public square, a church, a palace, a monument and much more! Start your day with a visit to Rialto Bridge. This iconic historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza San Marco, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Venice 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 St Mark's Basilica, a popular church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Doge's Palace and Bridge Of Sighs.

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.

Experience a taste of local culinary excellence while in Bologna by securing a table at Ahimè. An esteemed Bib Gourmand restaurant, it features an exceptional country cooking menu. For an alternative taste experience, visit I Portici, famous for its scrumptious creative and contemporary dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.

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.

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

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.

Prepare for a day full of fun adventures, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Two Towers. This captivating monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Maggiore, one of the city’s best highlights.

Next, check out Siena Cathedral, one of the most captivating places to see in Bologna. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Campo. Wander around and soak in the visually striking atmosphere this public square offers. Then, head to Tower Of Mangia, a top-rated monument that adds another dimension to your day.

At the end of the day, you will drive to Arezzo, 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 Arezzo's best restaurants.

Enjoy an outstanding dining experience at Octavin, a 1-star Michelin restaurant offering an exceptional creative menu. Alternatively, experience a taste of Arezzo at La Clandestina, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated.

Cap off your dinner by heading to Liquid Bar, ideal for a leisurely evening with a drink in hand.

Savor another day of unforgettable experiences 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 4 nights here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Arezzo allows for both. Start by heading to Vatican Museums. This wondrous art museum provides an insightful glimpse into the city's identity.

Continue your sightseeing with a visit to Saint Peter's Square, a captivating square. When you’re done, don’t forget to make a stop at the timeless St. Peter's Basilica.

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

As 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.

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

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 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.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and history-rich sites. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Foro Italico is the first of them. Spend some time admiring this standout sports complex before continuing your journey. Piazza Del Popolo is your next stop. This widely recognized 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 eye-catching 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 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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Sant' Eustachio Caffè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yellowsquare Rome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino is also a great option that provides a perfect setting for a relaxing evening.

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Colosseum. This timeless 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 interesting 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 picture-perfect 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 activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Treat yourself to a 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.

Cap off your dinner by heading to The Apartment Bar Roma, ideal for a leisurely evening with a drink in hand. Hotel Hassler Roma is another bar that offers an enjoyable setting.

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

Day 10 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Orange Garden, a notable park in the city. Then, head to Circus Maximus and soak in the ambiance of this picture-perfect archeological site.

There are many interesting places to see in Rome and when you are ready for more, go to Campo De' Fiori. This is one of the city’s most famous spots. After exploring the public square, visit the world-famous Piazza Navona. Before wrapping up your self-guided sightseeing tour, head to the widely recognized Castel Sant'angelo, a widely recognized castle 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 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 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.

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

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.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a monument, a public square, and a concert hall. Begin your adventure at Pantheon. This is a wondrous monument you should not miss. Another must-see is Trevi Fountain, a globally renowned monument in Rome.

When you’re ready for the next sight, head to Piazza Di Spagna. From there, take a leisurely stroll to Spanish Steps, another of the city’s astonishing attractions. We recommend continuing your self-guided tour at Auditorium Parco Della Musica, a picture-perfect 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 Florence. Florence 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 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.

Experience a symphony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enoteca Pinchiorri delights its guests with its exceptional variety of meals showcasing delicious italian contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Santa Elisabetta, acclaimed for its delectable creative and mediterranean specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Gucci Osteria da Massimo Bottura, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and international cuisine in the city.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

On day 12 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in Florence. Begin your sightseeing with Basilica Di Santa Maria Novella, Firenze (fi). This locally renowned church is one of the top attractions in the city. Proceed to Central Market, another must-visit attraction that enhances the city’s allure.

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 widely recognized 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.

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

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

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

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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Della Signoria. This romantic public square is sure to ignite your curiosity. Next, dive into the visually striking features of Ponte Vecchio, a must-visit historical landmark 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 Uffizi Gallery, a top-rated art gallery. For a change of scene, check out Basilica Of Santa Croce In Florence, known for its heritage-rich features.

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

As you explore more of 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.

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at 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.

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

Dive into day 14 of your remarkable road trip in Italy. Today you will explore Pisa and Genoa, 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 Milan. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Pisa. Some of the city’s most loved attractions await. Leaning Tower Of Pisa is the perfect place to start. This monument is one of the most iconic places to visit in Pisa. Next, head to Piazza Del Duomo, Pisa, an iconic public square, known for its symbolic 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 Pisa Cathedral. This majestic church offers a unique experience that is highly recommended. Meanwhile, Spiaggia Pubblica Di Priaruggia adds its own distinct charm to your journey.

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

After a 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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Qc Termemilano, known for its inviting atmosphere. Yguana Cafè 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!