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

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, a famous castle, located just a leisurely stroll away. Next, head to Galleria Vittorio Emanuele Ii, a visually striking shopping mall, also available for your discovery today.

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

Enjoy a lovely dining experience at Dessert Bar Milano, 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 Radisson Blu Hotel Milan, 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 Qui Si Mangia. It’s yet another ideal choice to enhance your time in Milan tonight.

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

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.

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

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

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 Rogaro and hit the road. Expect a journey of approximately 8 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Rogaro 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 Carlotta (lake Como), an underrated museum that everyone visiting Rogaro should see. Next, head to Botanical Garden Of Villa Carlotta. This standout botanical garden is one of the most curiosity-inducing attractions in the region.

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

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.

Dine in style at Bice Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Alto Ristorante boasts a menu that's sure to impress. Also, be sure to check out Nero 9. Known as a local hotspot, it’s a great choice for tonight in Milan.

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

Explore the vibrant nightlife at Bhangrabar after your meal, a hub for lively evenings and memorable moments. Or, head to Rufus Cocktail Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Ostello Bello Grande is perfect for those looking to extend their night with a touch of local flavor.

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

Day 4 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Verona. By evening, drive toward the Venice, where you’ll stay at a top-rated hotel of your choice for 3 nights.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Verona. Your travel time is around 2 hours 7 min.

For a more meaningful self-guided tour of the city's best attractions, visit Verona Arena, an iconic stadium that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Porta Borsari and admire its symbolic features.

When you’re ready, continue to Piazza Delle Erbe, an interesting public square beloved by locals and tourists alike. Don't miss out on Piazza Dei Signori, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Ponte Pietra, a history-steeped place to see that you won’t regret spending some extra time discovering.

In Venice, 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.

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.

Make sure to reserve a table at Bauer Hotel, 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 L'Osteria Le Guglie, 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 Corner Pub, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

After enjoying a fulfilling meal, continue your evening at Al Parlamento, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Caffe Rosso offers a welcoming atmosphere for easing into the nightlife. Similarly, Adagio provides an excellent environment for a relaxed and enjoyable evening.

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

Day 5 introduces you to many popular attractions and activities in Venice, further proving that leisurely self-drive tours in Italy are extraordinary.

Whatever your travel style is, Bridge Of Sighs is an essential stop in Venice. This captivating monument provides an insightful glimpse into the city's identity. Next, discover Doge's Palace, a romantic palace, promising a delightful encounter.

Continue your sightseeing with a visit to St Mark's Basilica, a notable church. When you’re done, don’t forget to make a stop at the globally renowned Piazza San Marco. Round off your day at Rialto Bridge, another gem in Venice with visually striking features to discover.

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.

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.

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

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.

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

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Venice, where you'll stay for 1 night, 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!

No visit to Venice is complete without Palazzo Contarini Del Bovolo. This captivating palace is one of the top attractions in the city. Proceed to Teatro La Fenice, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Peggy Guggenheim Collection. This captivating art gallery is a traveler-favorite. Not far away, you’ll find Santa Maria Della Salute, another key site on your sightseeing itinerary.

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 Venice to find the best options for you!

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 lovely meal at Osteria Alla Staffa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Bistrot de Venise is another top choice with a popular menu. You could also check for a table at Corte Sconta. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Venice tonight.

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

Continue your lively evening at Dolce Vita Venezia, a perfect place for winding down or revving up the night, depending on which mood you’re in. Tarnowska's American Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar All'angolo ensures a night out tailored to your taste.

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

Day 7 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Florence and end it in Florence. You’ll stay in Florence for 3 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Embrace the thrill of the open road as you wave goodbye to Venice and set your GPS to Florence. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 51 min. Upon reaching Florence, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Medici Chapels, an up-and-coming museum that everyone visiting Florence should see. Next, head to Riccardi Medici Palace. This instagrammable palace is one of the most worthwhile attractions in the region.

If you're keen to see more, don’t miss out on Brunelleschi's Dome, an enchanting monument popular among locals as well as travelers.

You'll be staying in Florence on this laid-back road trip through Italy. You'll stay here for 3 nights.

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 Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

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

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

Free your mind of worries as you enjoy the taste of freedom on your laid-back 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!

Oltrarno is a fantastic place you can explore today in Florence. 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 Florence-way-of-life and visit all the nearby sights.

Catch Piazza Della Signoria before the crowds roll in. This noteworthy public square is sure to ignite your curiosity. Next, dive into the detailed features of Bargello National Museum, a must-visit 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 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 delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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

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.

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

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 16 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Savor the day by heading to Piazza Del Duomo, Pisa, a world-famous public square that draws visitors from near and far. When you're done, continue to Pisa Cathedral, where you can soak in the UNESCO world heritage-designated surroundings.

Next, explore Angelo Caduto, yet another intriguing place to see in the area. After the sightseeing destination, make time to go to Leaning Tower Of Pisa. This breathtaking monument is well worth the visit.

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

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. Known for great service, it’s a fantastic choice for tonight 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.

Extend your evening after a delightful meal by visiting Gosh*, which offers the perfect atmosphere for a night out. Moreover, Antico Caffè Del Moro - Art Bar Firenze is another popular option for a drink or two. Likewise, Quelo Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 10 min. When you arrive in Siena, it's time to take a break from the road.

When you're ready for some sights, head to Fontan Kontradi Sel'va, a locally appreciated point of interest in Siena. This captivating church is a top recommendation in the area.

When you’re ready to explore more, Battistero Di San Giovanni Battista is an excellent choice. Spend some time discovering what some claim to be the most standout church in the region. Next, continue your sightseeing at the astonishing Piazza Del Campo and discover what makes this public square unique.

After a day of exploration, relax at one of the top hotels or accommodations in Rome. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip in Italy.

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 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 consistently gains 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.

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.

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

Day 11 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Make sure to visit Monti, a popular neighborhood 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. You can also explore Via dei Condotti today, a street that’s well worth a visit.

Make a stop at Piazza Di Spagna. This iconic public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Colosseum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Roman Forum. Its picture-perfect features will captivate you.

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.

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.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

Continue your evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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 12 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Rome and beyond. With 2 nights left in Rome, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

Don’t miss Trastevere 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.

To truly experience Rome, make sure to drop by Castel Sant'angelo. This spectacular 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 iconic 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.

St. Peter's Basilica is a globally renowned major basilica we recommend visiting today.

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.

Enjoy a lovely dining experience at Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar. It’s yet another ideal choice to enhance your time in Rome tonight.

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

After savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

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

On day 13 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 1 night, 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!

A top thing to do today is to explore Via del Corso, a must-see street in Rome. It's the perfect starting point for touring the top attractions in the area.

Altare Della Patria makes a great addition to your morning plans. This locally renowned monument is a historic place to see in Rome. Continue your discovery at Trevi Fountain, a visually striking monument with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Popolo. This famous public square offers a romantic encounter with Rome. Next, make your way to Villa Borghese to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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.

Enjoy a delicious meal at Sofitel Roma Villa Borghese, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Centro, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome 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 Rome. The bars in Rome make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

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