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

On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, 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 Milan, and meet locals along the way!

A top thing to do today is to explore Navigli, a must-see neighborhood in Milan. It's the perfect starting point for touring the top attractions in the area.

Parco Sempione is must-visit park and a great option for a daytime tour of the area. Continue your journey to Sforzesco Castle Art Library, an astonishing castle, located just a leisurely stroll away. Next, head to Galleria Vittorio Emanuele Ii, a history-steeped shopping mall, also available for your discovery today.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Milan. There are so many fun and eye-opening activities to try out in Milan 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 Milan 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 Milan, 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 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 consistently gains high praises from customers, it’s an ideal choice in Milan tonight.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Kilburn Cocktail Bar Milano, known for its inviting atmosphere. Bar Frida is another great option if you’re looking for a place to get the night started. Similarly, The Friends Pub Milano provides a great setting to enjoy the night away.

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

Your relaxed road trip in Italy continues on day 3 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Milan and beyond. With 1 night left in Milan, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

Whether you decide to explore Lenno on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Set your GPS to Lenno and hit the road. Expect a journey of approximately 1 hour 25 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Lenno beckons with new experiences!

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Villa Del Balbianello, an up-and-coming villa that everyone visiting Lenno should see.

Rogaro’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Lenno behind. This drive usually takes around 8 min. Rogaro welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Villa Carlotta (lake Como) and explore the history-steeped features. Next, make your way to Botanical Garden Of Villa Carlotta, another highlight in Rogaro.

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

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.

Don’t miss out on dining at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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

Extend your evening after a delightful meal by visiting Bhangrabar, which offers the perfect atmosphere for a night out. Moreover, Rufus Cocktail Bar is another popular option for a drink or two. Likewise, Ostello Bello Grande also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 4 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Venice for 3 nights.

Verona’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Milan behind. This drive usually takes around 2 hours 7 min. Verona welcomes you with a multitude of unique vacation experiences.

Spend your afternoon discovering Verona Arena, a world-famous stadium known for its romantic features. Next, continue your sightseeing at Porta Borsari, a curiosity-inducing historical landmark.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Delle Erbe and uncover the details of this history-steeped public square. Make sure to also explore Piazza Dei Signori, a curiosity-inducing public square. For your last stop, consider Ponte Pietra, a romantic historical landmark that many travelers find worth the detour.

Continue your laid-back road trip in Italy as you make your way to Venice. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

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.

Savor the flavors at Bauer Hotel, a top pick for dinner tonight. Alternatively, L'Osteria Le Guglie beckons with its unique menu offerings. Also, consider Corner Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

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.

To truly maximize your evening out, consider visiting Al Parlamento after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to The Caffe Rosso, another bar with an inviting ambiance. Similarly, Adagio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 5 of your relaxed road trip through Italy means 24 hours of making the best memories in Venice. You’ll go sightseeing at famous attractions in Venice. 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 Venice!

Experience Bridge Of Sighs, a locally renowned monument in the city. Then, head to Doge's Palace and soak in the ambiance of this UNESCO world heritage-listed palace.

There are many interesting places to see in Venice, and when you are ready for more, go to St Mark's Basilica. This is one of the city’s most interesting culturally significant spots of interest. After exploring the church, visit the iconic Piazza San Marco. Not far away, you'll also find Rialto Bridge. This historical landmark is a romantic highlight in Venice.

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

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

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.

Continue your evening by exploring the vibrant nightlife scene at Il Mercante, a prime destination for a thrilling night out. Also, don’t forget to check out The Irish Pub Venezia, a bar that offers unique local touches. Likewise, Ai Stagneri provides an excellent alternative for a fun evening.

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

Palazzo Contarini Del Bovolo is perfect for a self-paced visit during the day. This enchanting palace is sure to impress. Next on your list is Teatro La Fenice, another must-visit landmark and captivating opera house renowned for its romantic 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 Peggy Guggenheim Collection. This detailed art gallery is an essential place to visit for anyone looking for the full Venice experience. We also recommend visiting Santa Maria Della Salute, an increasingly popular church.

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.

Treat yourself to a delicious dinner at Osteria Alla Staffa, an excellent option for tonight's dining. Looking for something different? Bistrot de Venise offers a tantalizing alternative with its diverse menu. And don’t miss Corte Sconta. Known for great service, it’s a fantastic choice for tonight in Venice.

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

Following your dinner, dive into the local bar culture at Dolce Vita Venezia. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Tarnowska's American Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar All'angolo provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 7 of your relaxed road trip in 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!

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Florence. This drive usually takes around 2 hours 51 min, without any stops or traffic disruptions.

Set out on a self-guided sightseeing tour at Medici Chapels and explore the symbolic features. Next, make your way to Riccardi Medici Palace, another highlight in Florence. When you’re done exploring the palace, continue to Brunelleschi's Dome, an inviting monument.

In Florence, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip 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 Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, 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 Florence, and meet locals along the way!

Don’t miss Oltrarno today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Visiting Piazza Della Signoria is always a good idea. This extraordinary public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the photogenic wonders of Bargello National Museum, a must-see museum in the city.

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.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Grab yourself a drink and savor every moment of your relaxed road trip experience in 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.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 1 hour 16 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Piazza Del Duomo, Pisa, a wondrous public square in Pisa. Explore its stunning features at your own pace before you continue your journey to your next attraction, Pisa Cathedral. This locally appreciated church is a top recommendation in the area.

When you’re ready to explore more, Angelo Caduto is an excellent choice. Next, continue your sightseeing at the timeless Leaning Tower Of Pisa and discover what makes this monument unique.

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.

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

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 10 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Siena and end it in Rome. You’ll stay in Rome for 4 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

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

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 10 min.

Fontan Kontradi Sel'va is an increasingly popular sightseeing destination we recommend visiting today.

Next, stop by Battistero Di San Giovanni Battista, a heritage-rich church. While you’re nearby, don’t forget to visit Piazza Del Campo, an UNESCO world heritage-designated and truly unique public square.

You'll be staying in Rome on this laid-back road trip through Italy. You'll stay here for 4 nights.

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.

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

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.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

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

Day 11 of your relaxed road trip through Italy means 24 hours of making the best memories in Rome. You’ll go sightseeing at famous attractions in Rome. 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 Rome!

Rome is brimming with adventures. Monti is a neighborhood that stands out as one of the must-see places in Rome. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away. For another highlight, head to Via dei Condotti, a street offering its own unique experiences.

Piazza Di Spagna leaves a lasting impression. This public square is one of the most wondrous places to visit in Rome. Next, head to Colosseum, a globally renowned archeological site, known for its picture-perfect 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 Roman Forum. This culturally significant archeological site is a highly recommended experience.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Milan. There are so many fun and eye-opening activities to try out in Milan 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 Rome to find the best options for you!

Exploring the food culture in Rome 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 wonderful meal at RomAntica, a top-rated dining spot in Rome. If you're in the mood for something new, try Coso Ristorante, another premier location with a delectable menu. You might also want to book a table at DEROMA - Farine Romane. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

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

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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

On day 12 of your relaxed road trip in Italy, you’ll start your self-paced adventure in Rome and visit amazing attractions in Vatican City and Rome, just outside the city. You still have 2 nights left in Rome, so today is another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Trastevere is one of the highlights of today. Take your time exploring this iconic neighborhood in Vatican City, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

To truly experience Rome, make sure to drop by Castel Sant'angelo. This impressive castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Navona, one of the city’s best highlights.

Next, check out Pantheon, one of the most globally renowned places to see in Rome. This monument is a favorite among locals and travelers alike.

Fasten your seatbelt and make your way to your next stop — Vatican City, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Vatican City may take around 11 min without traffic disruptions. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Savor the day by heading to St. Peter's Basilica, an iconic major basilica that draws visitors from near and far.

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

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 Hotel de Russie, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Taverna Italiana offers an enticing alternative with its varied menu. Additionally, The Parrot Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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

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.

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

One of the most iconic spots you can visit today is Via del Corso. Allow yourself some time to explore this street and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Look forward to a unique sightseeing adventure at the interesting Altare Della Patria and allow yourself time to explore. Just a short distance away you'll find your next stop, Trevi Fountain, a culturally significant monument that draws visitors from far and near.

Continue your journey to Piazza Del Popolo, one of the city’s most impressive spots that you shouldn’t miss. Another great site to visit is the astonishing Villa Borghese.

Italy makes the perfect setting for a calming but fun road trip experience. 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 Rome, explore the city like a local by trying out the best restaurants in the area.

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.

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.

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