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!

Make sure to visit Navigli, a popular neighborhood in Milan. 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.

Today's adventure in Milan promises more breathtaking discoveries and enriching experiences! Begin at Parco Sempione. This mesmerizing park is a highlight of any visit in the city. Then, enjoy Sforzesco Castle Art Library, another respected attraction that never fails to captivate visitors. Next, head over to Galleria Vittorio Emanuele Ii, one of the city’s most spectacular attractions, known for its remarkable features.

If you’re looking for more, spend time soaking in the atmosphere of Duomo Di Milano Museum. This majestic church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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 Milan 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.

Enjoy a lovely meal at Dessert Bar Milano, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Radisson Blu Hotel Milan is another top choice with a popular menu. You could also check for a table at Ristorante Qui Si Mangia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan 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.

Cap off your dinner by heading to Kilburn Cocktail Bar Milano, ideal for a leisurely evening with a drink in hand. Bar Frida is another bar that offers an enjoyable setting. Similarly, The Friends Pub Milano 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.

On day 3 of your relaxed road trip, you’ll start your self-paced adventure in Milan and visit amazing attractions in Lenno and Rogaro destinations, just outside of the city. You still have 1 night left in Milan. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Milan allows for both. Start by heading to Villa Del Balbianello. This intriguing villa provides an insightful glimpse into the village's identity. Next, discover Villa Carlotta (lake Como), a history-steeped museum, promising a delightful encounter.

Continue your sightseeing with a visit to Botanical Garden Of Villa Carlotta, an intriguing botanical garden.

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

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

Have a fantastic dining experience at Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

Following your dinner, dive into the local bar culture at Bhangrabar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Rufus Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Ostello Bello Grande provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

Day 4 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Verona. By the end of the day, you’ll drive in the direction of the city of Venice, where you’ll stay at a top-rated hotel of your choice for 3 nights.

Savor the day by visiting some of the best places to see in Milan, including a stadium, a historical landmark, and a public square. Start your adventure at Verona Arena. This timeless stadium is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta Borsari located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Piazza Delle Erbe. Its history-steeped features will captivate you. After the public square, continue your tour of the city with a visit to Piazza Dei Signori. Visitors usually appreciate the visually striking features of this public square. Next up is Ponte Pietra, a highly recommended historical landmark.

After a day of exploration, relax at one of the top hotels or accommodations in Venice. 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.

Exploring the food culture in Venice 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.

Treat yourself to a delightful dinner at Bauer Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try L'Osteria Le Guglie? It's another excellent option with a diverse menu. Consider reserving a table at Corner Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

If you feel like it, head out to a bar to celebrate another fantastic day in Venice and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

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

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

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!

Start by visiting Bridge Of Sighs, a prime spot to begin your journey. This visually striking monument is sure to impress. Next on your list is Doge's Palace, another must-visit landmark and interesting palace renowned for its UNESCO world heritage-listed features.

While exploring and sightseeing, take time to savor the culture of Venice by sampling some local delicacies. When you’re ready for more sightseeing, head to St Mark's Basilica. This history-steeped church is an essential place to visit for anyone looking for the full Venice experience. We also recommend visiting Piazza San Marco, a world-famous public square. Nearby, you'll also find Rialto Bridge, ready to add charm to your journey.

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

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

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

Before calling it a day, visit one of the best bars in Venice. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Explore the vibrant nightlife at Il Mercante after your meal, a hub for lively evenings and memorable moments. Or, head to The Irish Pub Venezia for a great selection of flavorful drinks and a charming setting. Furthermore, Ai Stagneri is perfect for those looking to extend their night with a touch of local flavor.

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

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

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the locally renowned Palazzo Contarini Del Bovolo, a visually striking palace in Venice. Next, go to Teatro La Fenice.

After visiting Palazzo Contarini Del Bovolo and Teatro La Fenice, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to Peggy Guggenheim Collection. This masterful art gallery offers a unique experience. Santa Maria Della Salute is another noteworthy attraction worthwhile a visit.

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.

Treat yourself to a delightful dinner at Osteria Alla Staffa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bistrot de Venise? It's another excellent option with a diverse menu. Consider reserving a table at Corte Sconta as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

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 Venice. The bars in Venice make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Keep the evening going at Dolce Vita Venezia, a great choice for enjoying the after-dinner hours with a drink. You could also go to Tarnowska's American Bar, which offers a similarly pleasant setting and great drinks. Another option is Bar All'angolo, which provides an inviting environment for unwinding after a busy day out.

A leisurely self-drive holiday in Venice can’t get any better than this! Toast to another amazing day in Italy!

Day 7 of your relaxed road trip across the beautiful country of Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

Venice is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and history-rich sites! Start at Medici Chapels, an up-and-coming museum that is worthwhile a visit in the city. Nearby, you’ll find Riccardi Medici Palace, enchanting visitors with its instagrammable appeal. Continue your exploration at Brunelleschi's Dome. This monument is one of the city’s most worthwhile spots.

In the city of Florence, 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 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.

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in 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!

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

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most spectacular attractions included on the itinerary is Piazza Della Signoria. This culturally significant public square will help you start your sightseeing on top. Then, take a leisurely stroll to Bargello National Museum and learn what makes this standout museum unique.

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

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 Florence, explore the city like a local by trying out the best restaurants in the area.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Cherish every minute of your relaxed road trip vacation across Italy.

On day 9 of your relaxed road trip across Italy, you’ll explore the area around Florence, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Florence will make you fall even more in love with the city and uniqueness of Italy.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, scenic views, and photo-friendly spots. Start at Piazza Del Duomo, Pisa, an iconic public square in the city. Then, head to Pisa Cathedral and soak in the ambiance of this stunning church.

After exploring the point of interest, visit the timeless Leaning Tower Of Pisa.

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

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 lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

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

Continue your lively evening at Gosh*, a perfect place for winding down or revving up the night, depending on which mood you’re in. Antico Caffè Del Moro - Art Bar Firenze is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Quelo Bar ensures a night out tailored to your taste.

A leisurely self-drive holiday in Pisa can’t get any better than this! Toast to another amazing day in Italy!

Day 10 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Siena and drive in the direction of the city of Rome for some laid-back sightseeing. You’ll end your day in the city of Rome, where you’ll stay for 4 nights.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Fontan Kontradi Sel'va. Then, enjoy Siena Cathedral, another inviting attraction that never fails to captivate visitors. Next, head over to Battistero Di San Giovanni Battista, one of the city’s most worthwhile attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Del Campo. This visually striking public square is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

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 Rome, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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.

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

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Grab yourself a drink and savor every moment of your relaxed road trip experience 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 wondrous public square that is worthwhile a visit in the city. Nearby, you’ll find Colosseum, enchanting visitors with its UNESCO world heritage-listed appeal. Continue your exploration at Roman Forum. This archeological site is one of the city’s most world-famous spots.

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.

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.

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Your laid-back and relaxed road trip in Italy continues on day 12, 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 Rome and beyond. With 2 nights left in Rome, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

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.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in Rome. Begin your sightseeing with St. Peter's Basilica. This globally renowned major basilica is one of the top attractions in the city. Proceed to Castel Sant'angelo, 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 Navona. This wondrous public square is a traveler-favorite. Not far away, you’ll find Pantheon, another key site on your sightseeing itinerary.

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

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 Rome, explore the city like a local by trying out the best restaurants in the area.

Don’t miss out on dining 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.

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.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

Toast to another unforgettable and relaxing road trip adventure 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.

Via del Corso is one of the highlights of today. Take your time exploring this iconic street in Rome, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Today, you'll explore some of the most beautiful places in Rome, including a monument, a public square, and a park. Start your day with a visit to Altare Della Patria. This popular monument is a must-visit in the city. When you’re ready for your next discovery, continue to Trevi Fountain, which may be one of the most enchanting 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 Piazza Del Popolo, a famous public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Villa Borghese.

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.

Treat yourself to a delicious dinner at Sofitel Roma Villa Borghese, an excellent option for tonight's dining. Looking for something different? Centro offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Tema. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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

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.