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.

Start by visiting Parco Sempione, a prime spot to begin your journey. This mesmerizing park is sure to impress. Next on your list is Sforzesco Castle Art Library, another must-visit landmark and widely recognized castle renowned for its picture-perfect features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to Galleria Vittorio Emanuele Ii. This masterful shopping mall is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Duomo Di Milano Museum, a timeless church.

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, Milan has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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.

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

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

On day 3 of your relaxed road trip across Italy, you’ll explore the area around Milan, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Milan will make you fall even more in love with the city and uniqueness of Italy.

Milan is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Villa Del Balbianello, an up-and-coming villa that is worthwhile a visit in the village. Nearby, you’ll find Villa Carlotta (lake Como), enchanting visitors with its history-steeped appeal. Continue your exploration at Botanical Garden Of Villa Carlotta. This botanical garden is one of the village’s most curiosity-inducing spots.

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

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.

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.

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.

If you’re not ready to end the night just yet, Bhangrabar offers a perfect venue to relax and savor a drink. Similarly, Rufus Cocktail Bar is well-suited for those looking to unwind in a social setting. Ostello Bello Grande is another excellent spot to enjoy a nightcap after a delightful meal.

Toast to another unforgettable and relaxing road trip adventure 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.

Milan is brimming with adventures. Today’s wonderful stops include a stadium, a historical landmark, and a public square. Begin your sightseeing adventure at the iconic Verona Arena and allow yourself time to explore. Just a short distance away you'll find your next stop, Porta Borsari, a symbolic historical landmark that draws visitors from far and near.

Continue your journey to Piazza Delle Erbe, one of the city’s most popular spots that you shouldn’t miss. Another great site to visit is the curiosity-inducing Piazza Dei Signori. When you're finished at the public square, Ponte Pietra awaits your visit. This historical landmark is a romantic highlight on today's itinerary.

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.

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.

Don’t miss out on dining at Bauer Hotel, a top-rated dining destination in Venice. If you're in the mood to try something new, consider L'Osteria Le Guglie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

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

After your meal, keep the night alive at a bar like Al Parlamento, known for its lively atmosphere. The Caffe Rosso is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Adagio offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass and toast to another unforgettable, laid-back 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.

Immerse yourself in Venice’s rich culture with today's sightseeing itinerary. Start your journey at Bridge Of Sighs. This history-steeped monument is sure to ignite your curiosity. Next, dive into the majestic features of Doge's 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 St Mark's Basilica, a popular church. For a change of scene, check out Piazza San Marco, known for its visually striking features. We also recommend visiting Rialto Bridge. This historical landmark is a must for anyone looking to experience the city to the fullest.

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!

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 Generator Venice, a top pick for dinner tonight. Alternatively, Nevodi beckons with its unique menu offerings. Also, consider Ristorante La Piazza. With its consistent customer satisfaction, it’s an excellent option for dining in Venice 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.

After your meal, keep the night alive at a bar like Il Mercante, known for its lively atmosphere. The Irish Pub Venezia is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ai Stagneri offers an excellent atmosphere for those looking to amp up the evening.

Cherish every minute of your relaxed road trip vacation across 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!

Get ready for an exciting day in Venice. Today’s sightseeing agenda includes a palace, an opera house, an art gallery, a church and much more! Begin your adventure at Palazzo Contarini Del Bovolo. This is a notable palace you should not miss. Another must-see is Teatro La Fenice, a popular opera house in Venice.

When you’re ready for the next sight, head to Peggy Guggenheim Collection. From there, take a leisurely stroll to Santa Maria Della Salute, another of the city’s curiosity-inducing attractions.

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.

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 delicious meal at Osteria Alla Staffa, a highly-rated dining destination in Venice. If you're eager to try something different, consider Bistrot de Venise, another top spot with a tantalizing menu. You might also want to secure a reservation at Corte Sconta. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

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

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.

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

Day 7 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Florence for 3 nights.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and history-rich sites. Whether you decide to explore Venice on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Medici Chapels is the first of them. Spend some time admiring this respected museum before continuing your journey. Riccardi Medici Palace is your next stop. This curiosity-inducing palace is one of the best-rated sights in Venice.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Brunelleschi's Dome. This enchanting monument is a sight to behold.

Continue your laid-back road trip exploration of the best attractions in Italy at Florence. 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 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 Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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!

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.

Savor the day by visiting some of the best places to see in Florence, including a public square and a museum. Start your adventure at Piazza Della Signoria. This widely recognized public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Bargello National Museum located in Florence for another exciting encounter.

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

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.

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.

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.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Your laid-back and relaxed road trip in Italy continues on day 9, 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 Florence and beyond. With 1 night left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Begin your adventure at Piazza Del Duomo, Pisa. This is a globally renowned public square you should not miss. Another must-see is Pisa Cathedral, a beloved church in Florence.

When you’re ready for the next sight, head to Angelo Caduto. From there, take a leisurely stroll to Leaning Tower Of Pisa, another of the city’s wondrous attractions.

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

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.

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly 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.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 10 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Rome for 4 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.

Start your adventure at Fontan Kontradi Sel'va. This intriguing sightseeing destination is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Siena Cathedral, a must-see church in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Battistero Di San Giovanni Battista. This up-and-coming church offers an enriching experience. For a change of pace, head to Piazza Del Campo, where you can take in history-steeped features. These sights offer a fulfilling end to a perfect day.

You’ll be staying at the incredible city of Rome in this laid-back road trip in 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.

Make sure to reserve a table at La Bottega Roma, 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 Pasta In Corso, 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 Trattoria Vecchia Roma, a hidden gem nestled in Rome. 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 Rome.

Extend your evening after a delightful meal by visiting La Botticella Of Poggi Giovanni, which offers the perfect atmosphere for a night out. Moreover, Almalu Trastevere is another popular option for a drink or two. Likewise, Bar Viminale Di Pepi Maurilio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Toast to another unforgettable and relaxing road trip adventure 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.

A top thing to do today is to explore Monti, a must-see neighborhood in Rome. It's the perfect starting point for touring the top attractions in the area. You can also visit Via dei Condotti, an ideal street for continued sightseeing.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most world-famous attractions included on the itinerary is Piazza Di Spagna. This romantic public square will help you start your sightseeing on top. Then, take a leisurely stroll to Colosseum and learn what makes this UNESCO world heritage-listed archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the globally renowned Roman Forum.

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.

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 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.

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.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino 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 Rome!

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

Make sure to visit Trastevere, a popular neighborhood in Vatican City. 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.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at St. Peter's Basilica. This timeless major basilica is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Castel Sant'angelo, one of the city’s best highlights.

Next, check out Piazza Navona, one of the most iconic places to see in Rome. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pantheon. Wander around and soak in the culturally significant atmosphere this monument offers.

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

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.

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.

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.

Unwind after your meal by stepping into The Apartment Bar Roma. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Hassler Roma offers a dynamic and energetic atmosphere for a glass or two.

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!

At the top of the list of things to do today is to explore Via del Corso, a street 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.

A blend of fun adventures, scenic views, and photo-friendly spots await you in Rome on today’s itinerary. First up is the interesting monument, Altare Della Patria. Afterward, continue to Trevi Fountain, a monument 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 Del Popolo. This astonishing public square is an essential stop. Following that, head to Villa Borghese, another must-visit site that will enhance your experience.

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

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 lovely meal at Sofitel Roma Villa Borghese, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Centro is another top choice with a popular menu. You could also check for a table at Ristorante Tema. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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.

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