Two-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Venice, Florence, and Rome

Day 2 of your relaxed road trip through Italy means 24 hours of making the best memories in Milan. You’ll go sightseeing at famous attractions in Milan. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Milan!

Navigli is a neighborhood that stands out as one of the must-see places in Milan. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Get ready for a day filled with fun adventures, romantic experiences, and natural wonders in the charming city of Milan. Your adventure starts at Parco Sempione, a widely recognized local hot spot. Another notable attraction to explore is Sforzesco Castle Art Library. This famous castle is known for its serene appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Galleria Vittorio Emanuele Ii. This masterful shopping mall offers a fascinating experience that many visitors find memorable. Duomo Di Milano Museum is also worth visiting.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Milan offers a wide selection of experiences for every traveler.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Treat yourself to a delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

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

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

Your laid-back and relaxed road trip in Italy continues on day 3, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Milan and beyond. With 1 night left in Milan, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Just a short distance away you'll find your next stop, Villa Carlotta (lake Como), a masterful museum that draws visitors from far and near.

Continue your journey to Botanical Garden Of Villa Carlotta, one of the village’s most often recommended spots that you shouldn’t miss.

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

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Milan, explore the city like a local by trying out the best restaurants in the area.

Treat yourself to a delicious dinner at Bice Restaurant, an excellent option for tonight's dining. Looking for something different? Alto Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss Nero 9. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

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.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

Day 4 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Venice for 3 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Get ready to discover some of the most iconic wonders in Milan, including a stadium, a historical landmark, and a public square. Start your day at Verona Arena. This visually striking stadium is a timeless place to see in Milan. Then, wander over to Porta Borsari. If heritage-rich sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Piazza Delle Erbe. This visually striking public square 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, Piazza Dei Signori is a worthwhile spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the enchanting Ponte Pietra. Take a moment to appreciate the fascinating details of this popular historical landmark.

In the city of Venice, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Venice, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a delicious dinner at Bauer Hotel, an excellent option for tonight's dining. Looking for something different? L'Osteria Le Guglie offers a tantalizing alternative with its diverse menu. And don’t miss Corner Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

Experience the amazing nightlife in Venice and unwind at the coolest bars in the city.

After savoring a delicious meal, step into the vibrant nightlife at Al Parlamento, where the evening is just getting started. In the same way, The Caffe Rosso offers a unique charm perfect for experiencing the local bar scene in Venice. Adagio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

On day 5 of your leisurely self-drive tour across Italy, you’ll go deep into Venice, where you'll stay for 2 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Venice, and meet locals along the way!

Savor the day by visiting some of the best places to see in Venice, including a monument, a palace, a church, a public square, a historical landmark and much more! Start your adventure at Bridge Of Sighs. This notable monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Doge's Palace located in Venice for another exciting encounter.

Next, immerse yourself in the setting of St Mark's Basilica. Its visually striking features will captivate you. After the church, continue your tour of the city with a visit to Piazza San Marco. Visitors usually appreciate the visually striking features of this public square. Next up is Rialto Bridge, a highly recommended historical landmark.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Venice, explore the city like a local by trying out the best restaurants in the area.

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

After dinner, it’s time to fall in love with the amazing nightlife in Venice and unwind at some of the best bars in the city.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Il Mercante, known for its inviting atmosphere. The Irish Pub Venezia is another great option if you’re looking for a place to get the night started. Similarly, Ai Stagneri provides a great setting to enjoy the night away.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

Day 6 introduces you to many popular attractions and activities in Venice, further proving that leisurely self-drive tours in Italy are extraordinary.

Brace yourself for today’s incredible lineup of attractions in Venice, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Palazzo Contarini Del Bovolo, an interesting palace in the city. Then, head to Teatro La Fenice and soak in the ambiance of this romantic opera house.

There are many interesting places to see in Venice, and when you are ready for more, go to Peggy Guggenheim Collection. This is one of the city’s most locally renowned visually striking spots of interest. After exploring the art gallery, visit the increasingly popular Santa Maria Della Salute.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Venice. There are so many fun and eye-opening activities to try out in Venice that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Venice to find the best options for you!

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Venice, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a lovely dining experience at Osteria Alla Staffa, a popular restaurant in Venice. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Venice at Bistrot de Venise, 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 Corte Sconta. It’s yet another ideal choice to enhance your time in Venice tonight.

As the day is coming to an end, stop at some of Venice’s best bars to celebrate this day of your slow-paced adventure in Italy.

After enjoying a fulfilling meal, continue your evening at Dolce Vita Venezia, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tarnowska's American Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar All'angolo provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

On day 7 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Immerse yourself in Venice’s rich culture with today's sightseeing itinerary. Start your journey at Medici Chapels. This photogenic museum is sure to ignite your curiosity. Next, dive into the heritage-rich features of Riccardi Medici Palace, a must-visit palace 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 Brunelleschi's Dome, an intriguing monument.

After a day of exploration, relax at one of the top hotels or accommodations in Florence. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Florence. The bars in Florence make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across Italy.

Day 8 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

Set aside time today to explore Oltrarno, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Piazza Della Signoria. This top-rated public square provides an insightful glimpse into the city's identity. Next, discover Bargello National Museum, a detailed museum, promising a delightful encounter.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Exploring the food culture in Florence offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

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.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

Soak in the unique atmosphere of Florence as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday in Italy!

On day 9 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in Pisa destinations, just outside of the city. You still have 1 night left in Florence. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most wondrous attractions included on the itinerary is Piazza Del Duomo, Pisa. This stunning public square will help you start your sightseeing on top. Then, take a leisurely stroll to Pisa Cathedral and learn what makes this historic church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the intriguing Angelo Caduto. After exploring the point of interest, head to Leaning Tower Of Pisa. This wondrous monument is a highlight in Florence.

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

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Hang out and unwind at some of the top bars in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Gosh*, a well-loved spot among locals and tourists. Or, head to Antico Caffè Del Moro - Art Bar Firenze. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Quelo Bar, another top-rated place in the area.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

Day 10 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Rome for 4 nights.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in Florence. Begin your sightseeing with Fontan Kontradi Sel'va. This often recommended sightseeing destination is one of the top attractions in the city. Proceed to Siena Cathedral, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Battistero Di San Giovanni Battista. This frequently visited church is a traveler-favorite. Not far away, you’ll find Piazza Del Campo, another key site on your sightseeing itinerary.

Continue your laid-back road trip exploration of the best attractions in Italy at Rome. Select from top hotels and accommodations in the city to recharge and rejuvenate.

Exploring new places makes you hungry. Luckily, Rome has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Enjoy a lovely meal at La Bottega Roma, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Pasta In Corso is another top choice with a popular menu. You could also check for a table at Trattoria Vecchia Roma. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Following your dinner, dive into the local bar culture at La Botticella Of Poggi Giovanni. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Almalu Trastevere, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Toast to another unforgettable and relaxing road trip adventure in Italy!

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 3 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

At the top of the list of things to do today is to explore Monti, a neighborhood that captures the true essence of Rome. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions. Another must-visit is Via dei Condotti, a street offering a different perspective on Rome.

Rome is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Piazza Di Spagna, a world-famous public square that is worthwhile a visit in the city. Nearby, you’ll find Colosseum, enchanting visitors with its culturally significant appeal. Continue your exploration at Roman Forum. This archeological site is one of the city’s most wondrous spots.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Rome offers a wide selection of experiences for every traveler.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Rome.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

After savoring a delicious meal, step into the vibrant nightlife at Sant' Eustachio Caffè, where the evening is just getting started. In the same way, Yellowsquare Rome offers a unique charm perfect for experiencing the local bar scene in Rome. Caffè Portofino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

On day 12 of your relaxed road trip across Italy, you’ll explore the area around Rome, where you’ll be staying for another 2 nights. With so many fun and inspiring experiences to offer, a tour of Rome will make you fall even more in love with the city and uniqueness of Italy.

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Rome on today’s itinerary. First up is the iconic major basilica, St. Peter's Basilica. Afterward, continue to Castel Sant'angelo, a castle every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Navona. This world-famous public square is an essential stop. Following that, head to Pantheon, another must-visit site that will enhance your experience.

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

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation 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.

After dinner, it’s time to fall in love with the amazing nightlife in Rome and unwind at some of the best bars in the city.

Keep the evening going at The Apartment Bar Roma, a great choice for enjoying the after-dinner hours with a drink. You could also go to Hotel Hassler Roma, which offers a similarly pleasant setting and great drinks.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Day 13 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Make sure to visit Via del Corso, a popular street in Rome. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Altare Della Patria is the perfect place to start. This monument is one of the most popular places to visit in Rome. Next, head to Trevi Fountain, a timeless monument, known for its visually striking 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 Piazza Del Popolo. This enchanting public square is a highly recommended experience. Nearby, you'll also find Villa Borghese. Visit these for an interesting touch to your journey.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

Exploring new places makes you hungry. Luckily, Rome has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Savor the flavors at Sofitel Roma Villa Borghese, a top pick for dinner tonight. Alternatively, Centro beckons with its unique menu offerings. Also, consider Ristorante Tema. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Rome.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Rome!