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!

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.

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await! Parco Sempione is the perfect place to start. This park is one of the most extraordinary places to visit in Milan. Next, head to Sforzesco Castle Art Library, an impressive castle, known for its respected 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 Galleria Vittorio Emanuele Ii. This romantic shopping mall is a highly recommended experience. Nearby, you'll also find Duomo Di Milano Museum. Visit these for an interesting touch to your journey.

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

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.

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

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

Let the evening flow smoothly from dinner to drinks at Kilburn Cocktail Bar Milano, a top-rated bar in the area. For other recommendations, Bar Frida provides a perfect setting for rounding out your night with style and great drinks. Likewise, The Friends Pub Milano 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, relaxed road trip adventure across 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.

Start your adventure at Villa Del Balbianello. This increasingly popular villa is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Villa Carlotta (lake Como), a must-see museum in the village.

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 Botanical Garden Of Villa Carlotta. This up-and-coming botanical garden offers an enriching experience. These sights offer a fulfilling end to a perfect day.

When you’re done exploring for the day, you’ll return to Milan 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 Milan, 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 Bice Restaurant, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Alto Ristorante, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Unwind after your meal by stepping into Bhangrabar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Rufus Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Ostello Bello Grande, another top-rated bar in the area.

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

Day 4 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Verona and drive in the direction of the city of Venice for some laid-back sightseeing. You’ll end your day in the city of Venice, where you’ll stay 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 timeless 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 interesting spots that you shouldn’t miss. Another great site to visit is the up-and-coming Piazza Dei Signori. When you're finished at the public square, Ponte Pietra awaits your visit. This historical landmark is a grand highlight on today's itinerary.

You’ll be staying at the incredible city of Venice in this laid-back road trip in Italy. You'll stay here for 3 nights.

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.

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.

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

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.

A blend of fun adventures, romantic experiences, and scenic views await you in Venice on today’s itinerary. First up is the captivating monument, Bridge Of Sighs. Afterward, continue to Doge's Palace, a palace every traveler should visit.

As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to St Mark's Basilica. This notable church is an essential stop. Following that, head to Piazza San Marco, another must-visit site that will enhance your experience. Don’t forget to stop by Rialto Bridge, a wondrous historical landmark in the city.

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!

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.

Dine in style at Generator Venice, a top recommendation for dinner tonight. Or, for a change of pace, Nevodi boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Piazza. Known as a local hotspot, it’s a great choice for tonight in Venice.

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

Following your dinner, dive into the local bar culture at Il Mercante. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to The Irish Pub Venezia, the perfect place for those looking to experience the best of the nightlife. Similarly, Ai Stagneri provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 6 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!

Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most interesting attractions included on the itinerary is Palazzo Contarini Del Bovolo. This awe-inspiring palace will help you start your sightseeing on top. Then, take a leisurely stroll to Teatro La Fenice and learn what makes this romantic opera house unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Peggy Guggenheim Collection. After exploring the art gallery, head to Santa Maria Della Salute. This increasingly popular church is a highlight in Venice.

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 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 wonderful meal at Osteria Alla Staffa, a top-rated dining spot in Venice. If you're in the mood for something new, try Bistrot de Venise, another premier location with a delectable menu. You might also want to book a table at Corte Sconta. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Venice.

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.

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.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience 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, picturesque spots, and historic treasures! Start at Medici Chapels, an often recommended museum that is worthwhile a visit in the city. Nearby, you’ll find Riccardi Medici Palace, enchanting visitors with its respected appeal. Continue your exploration at Brunelleschi's Dome. This monument is one of the city’s most worthwhile spots.

When you’re not exploring beautiful places, you’ll have a relaxed time at Florence. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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

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

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

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!

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.

Florence is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Piazza Della Signoria, a famous public square that is worthwhile a visit in the city. Nearby, you’ll find Bargello National Museum, enchanting visitors with its photogenic appeal.

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.

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

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

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

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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

Just a short distance away you'll find your next stop, Pisa Cathedral, an UNESCO world heritage-listed church that draws visitors from far and near.

Continue your journey to Angelo Caduto, one of the city’s most worthwhile spots that you shouldn’t miss. Another great site to visit is the iconic Leaning Tower Of Pisa.

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

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

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

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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

Day 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.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Fontan Kontradi Sel'va, a worthwhile sightseeing destination in the city. Then, head to Siena Cathedral and soak in the ambiance of this symbolic church.

There are many interesting places to see in Florence, and when you are ready for more, go to Battistero Di San Giovanni Battista. This is one of the city’s most up-and-coming culturally significant spots of interest. After exploring the church, visit the impressive Piazza Del Campo.

In the city of Rome, 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 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.

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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

Round off your dining experience by visiting La Botticella Of Poggi Giovanni, a prime location for a drink. Alternatively, explore the distinctive characteristics of Almalu Trastevere, a bar catering to every mood and preference. Bar Viminale Di Pepi Maurilio likewise offers a unique atmosphere, perfect for a memorable night out.

Grab yourself a drink and savor every moment of your relaxed road trip experience 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 visit to Monti in Rome is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights. Don’t forget to check out Via dei Condotti as well, a street that adds another layer to your exploration.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the wondrous Piazza Di Spagna, a history-steeped public square in Rome. Next, go to Colosseum.

After visiting Piazza Di Spagna and Colosseum, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Roman Forum. This UNESCO world heritage-listed archeological site offers a unique experience.

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.

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

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

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 delicious meal, get a taste of the vibrant nightlife with a visit to Sant' Eustachio Caffè, known for its inviting atmosphere. Yellowsquare Rome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

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

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.

One of the most iconic places you can visit today in Vatican City is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at St. Peter's Basilica. Then, enjoy Castel Sant'angelo, another enchanting attraction that never fails to captivate visitors. Next, head over to Piazza Navona, one of the city’s most wondrous attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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

Cap off your dinner by heading to The Apartment Bar Roma, ideal for a leisurely evening with a drink in hand. Hotel Hassler Roma is another bar that offers an enjoyable setting.

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

Day 13 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!

Set aside time today to explore Via del Corso, a standout street 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.

Prepare for a day full of fun adventures, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Altare Della Patria. This locally renowned monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Trevi Fountain, one of the city’s best highlights.

Next, check out Piazza Del Popolo, one of the most widely recognized 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, Villa Borghese. Wander around and soak in the masterful atmosphere this park offers.

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!

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 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.

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

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