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

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

Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a church, a shopping mall, an opera house, a castle, a park and much more! Begin your adventure at Duomo Di Milano Museum. This is a globally renowned church you should not miss. Another must-see is Galleria Vittorio Emanuele Ii, an impressive shopping mall in Milan.

When you’re ready for the next sight, head to La Scala. From there, take a leisurely stroll to Sforzesco Castle Art Library, another of the city’s impressive attractions. We recommend continuing your self-guided tour at Parco Sempione, an eye-catching 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.

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.

Dive into a culinary adventure like no other in Milan by booking a table at Enrico Bartolini al Mudec. This popular restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another culinary dining option, venture to Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Il Luogo Aimo e Nadia, a top local restaurant known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Continue the enjoyment post-dinner at Kilburn Cocktail Bar Milano, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Frida offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out The Friends Pub Milano. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Milan, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today's adventure in Milan promises more breathtaking discoveries and enriching experiences! Begin at Pinacoteca Di Brera. This photogenic art gallery is a highlight of any visit in the city. Then, enjoy Beach Brema Sirmione, another serene attraction that never fails to captivate visitors. Next, head over to Scaliger Castle, one of the city’s most extraordinary attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Archaeological Site Of Grotte Di Catullo. This enchanting archeological site is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

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

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

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

Raise your glass to another unforgettable day in Italy!

On day 4 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 Verona. In the evening, you’ll end up in Venice, where you will stay for 1 night.

Today’s itinerary in Milan covers several incredible sights, including a museum, a monument, a stadium, a public square and much more! Start your adventure at Castelvecchio Museum. This popular museum is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Castelvecchio Bridge, a must-see monument 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 Verona Arena. This world-famous stadium offers an enriching experience. For a change of pace, head to Piazza Delle Erbe, where you can take in visually striking features. These sights offer a fulfilling end to a perfect day.

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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Venice. 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 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.

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.

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

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the iconic Rialto Bridge, a majestic historical landmark in Venice. Next, go to Piazza San Marco.

After visiting Rialto Bridge and Piazza San Marco, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to St Mark's Basilica. This majestic church offers a unique experience. Doge's Palace is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Bridge Of Sighs, one of the most UNESCO world heritage-listed places to visit in Venice.

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 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.

Have a memorable dining experience in Bologna by booking a table at Ahimè, renowned as a Bib Gourmand restaurant presenting an exceptional country cooking menu. For a different culinary experience in Bologna, I Portici shines as one of the top destinations, known for its delicious creative and contemporary 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, Trattoria di Via Serra is known as a top local spot for its delicious emilian cuisine in Bologna. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

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.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Bologna and Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Arezzo. You will spend 1 night here for some well-deserved relaxation.

A blend of family-friendly attractions, 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 popular 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 beloved 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.

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

Experience a taste of local culinary excellence while in Arezzo by securing a table at Octavin. An esteemed 1-star Michelin restaurant, it features an exceptional creative menu. If you're in the mood for something new, try La Clandestina, another premier location with a delectable menu.

Extend your evening after a delightful meal by visiting Liquid Bar, which offers the perfect atmosphere for a night out.

Raise your glass to another unforgettable day in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 4 nights.

Immerse yourself in Arezzo’s rich culture with today's sightseeing itinerary. Start your journey at Vatican Museums.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Saint Peter's Square, a captivating square.

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.

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

Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional 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.

Savor another day of unforgettable experiences in Italy!

On day 8 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 3 nights and discover all the best things to see and do in the area.

Today, you'll explore some of the most beautiful places in Rome, including a sport complex, a public square, a park, a church and much more! Start your day with a visit to Foro Italico. This captivating sports complex is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Popolo, 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 Villa Borghese, an impressive park in the city. If you’re up for more discoveries, don’t forget to reserve some time for 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.

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.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences 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.

Today’s agenda in Rome includes an archeological site, a public square, and a monument. Colosseum is must-visit archeological site and a great starting point for the day. Next, continue your journey to Roman Forum, a globally renowned archeological site, located just a leisurely stroll away. Next, head to Capitoline Hill, a majestic 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 well-known Altare Della Patria. If you’re looking for more, Largo Di Torre Argentina is also an interesting attraction that is worthwhile a visit.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

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

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night 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, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Orange Garden. This notable park is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Circus Maximus, one of the city’s best highlights.

Next, check out Campo De' Fiori, one of the most astonishing 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, Piazza Navona. Wander around and soak in the majestic atmosphere this public square offers. Then, head to Castel Sant'angelo, a top-rated castle 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.

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 highly-rated dining destination in Rome. If you're eager to try something different, consider Centro, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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

Dive into day 11 of your remarkable road trip in Italy. Today you will explore Rome, 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 Florence. You’ll stay here for 2 nights.

Discover a day packed with fun adventures, photo-friendly spots, and historic treasures in Rome. Begin your sightseeing with Pantheon. This wondrous monument is one of the top attractions in the city. Proceed to Trevi Fountain, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Di Spagna. This iconic public square is a traveler-favorite. Not far away, you’ll find Spanish Steps, another key site on your sightseeing itinerary. Auditorium Parco Della Musica is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

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.

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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 12 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Savor the day by visiting some of the best places to see in Florence, including a church, a food market, and an art gallery. Start your adventure at Basilica Di Santa Maria Novella, Firenze (fi). This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Central Market located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Cathedral Of Santa Maria Del Fiore. Its inviting features will captivate you. After the church, continue your tour of the city with a visit to Galleria Dell'accademia. Visitors usually appreciate the detailed features of this art gallery.

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 Florence's best restaurants.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 13 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 Florence. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazza Della Signoria. This impressive public square is a noteworthy place to see in Florence. Continue your discovery at Ponte Vecchio, a grand historical landmark with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Uffizi Gallery. This famous art gallery offers a romantic encounter with Florence. Next, make your way to Basilica Of Santa Croce In Florence to add another highlight to your day. After that, visit Piazzale Michelangelo, an astonishing observation deck that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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

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

Don’t miss out on dining 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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Jeffer Cocktails & Friends stands out as an excellent choice for a post-dinner cocktail. Alternatively, Le Parisien Wine Bar offers an ideal atmosphere to enjoy the pleasures of the night. Las Volta Cocktailbar is also a great option that provides a perfect setting for a relaxing evening.

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

Embark on another extraordinary experience on day 14 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Genoa. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.

Pisa is home to plenty of attractions that offer fun adventures, breathtaking views, and photo-friendly spots! Start at Leaning Tower Of Pisa, an iconic monument that is worthwhile a visit in the city. Nearby, you’ll find Piazza Del Duomo, Pisa, enchanting visitors with its majestic appeal. Continue your exploration at Pisa Cathedral. This church is one of the city’s most intriguing spots.

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

Enjoy a lovely dining experience at Ristorante la Brisa, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Pasticceria San Carlo, 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 UNAHOTELS Cusani Milano. It’s yet another ideal choice to enhance your time in Milan tonight.

Continue the enjoyment post-dinner at Qc Termemilano, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Yguana Cafè offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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.