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

Day 2 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.

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.

Today, you'll explore some of the most beautiful places in Milan, including a park, a castle, a shopping mall, a church and much more! Start your day with a visit to Parco Sempione. This top-rated park is a must-visit in the city. When you’re ready for your next discovery, continue to Sforzesco Castle Art Library, which may be one of the most stunning places you will experience today.

One of the best things about exploring Milan on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Galleria Vittorio Emanuele Ii, an astonishing shopping mall in the city. If you’re up for more discoveries, don’t forget to reserve some time for Duomo Di Milano Museum.

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 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.

Make sure to reserve a table at Dessert Bar Milano, 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 Radisson Blu Hotel Milan, 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 Ristorante Qui Si Mangia, a hidden gem nestled in Milan. 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 Milan.

Continue your evening by exploring the vibrant nightlife scene at Kilburn Cocktail Bar Milano, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Frida, a bar that offers unique local touches. Likewise, The Friends Pub Milano provides an excellent alternative for a fun evening.

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

Your laid-back and relaxed road trip in Italy continues on day 3, 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 Milan and beyond. With 1 night left in Milan, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Start your adventure at Villa Del Balbianello. This worthwhile villa is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the masterful 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 curiosity-inducing botanical garden offers an enriching experience.

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.

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

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Round off your dining experience by visiting Bhangrabar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Rufus Cocktail Bar, a bar catering to every mood and preference. Ostello Bello Grande 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 4 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Venice for 3 nights.

Today’s agenda in Milan includes a stadium, a historical landmark, and a public square. Verona Arena is must-visit stadium and a great starting point for the day. Next, continue your journey to Porta Borsari, a curiosity-inducing historical landmark, located just a leisurely stroll away. Next, head to Piazza Delle Erbe, an instagrammable public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. If you’re looking for more, Piazza Dei Signori is also an intriguing attraction that is worthwhile a visit. Lastly, don’t miss Ponte Pietra, a captivating gem to see in the city.

Continue your laid-back road trip exploration of the best attractions in Italy at Venice. Select from top hotels and accommodations in the city to recharge and rejuvenate.

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.

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.

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 your delicious meal, get a taste of the vibrant nightlife with a visit to Al Parlamento, known for its inviting atmosphere. The Caffe Rosso is another great option if you’re looking for a place to get the night started. Similarly, Adagio provides a great setting to enjoy the night away.

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 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!

Bring your curiosity for today’s adventure around Venice. Some of the city’s most loved attractions await. Bridge Of Sighs is the perfect place to start. This monument is one of the most captivating places to visit in Venice. Next, head to Doge's Palace, a notable palace, known for its history-steeped 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 St Mark's Basilica. This inviting church offers a unique experience that is highly recommended. Meanwhile, Piazza San Marco adds its own distinct charm to your journey. Finish your day with a visit to Rialto Bridge, a symbolic historical landmark 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.

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 Venice.

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.

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 enjoying a fulfilling meal, continue your evening at Il Mercante, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Irish Pub Venezia offers a welcoming atmosphere for easing into the nightlife. Similarly, Ai Stagneri provides an excellent environment for a relaxed and enjoyable evening.

Toast to another unforgettable and relaxing road trip adventure 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!

Savor the day by visiting some of the best places to see in Venice, including a palace, an opera house, an art gallery, a church and much more! Start your adventure at Palazzo Contarini Del Bovolo. This locally renowned palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Teatro La Fenice located in Venice for an enchanting atmosphere.

Next, immerse yourself in the setting of Peggy Guggenheim Collection. Its visually striking features will captivate you. After the art gallery, continue your tour of the city with a visit to Santa Maria Della Salute. This church has a majestic appeal.

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.

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.

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.

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.

If you’re not ready to end the night just yet, Dolce Vita Venezia offers a perfect venue to relax and savor a drink. Similarly, Tarnowska's American Bar is well-suited for those looking to unwind in a social setting. Bar All'angolo 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 7 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll end your day in the city of Florence, where you’ll stay for 3 nights.

Brace yourself for today’s incredible lineup of attractions in Venice, featuring fun adventures, picturesque spots, and history-rich sites. Start at Medici Chapels, an up-and-coming museum in the city. Then, head to Riccardi Medici Palace and soak in the ambiance of this standout palace.

There are many interesting places to see in Venice and when you are ready for more, go to Brunelleschi's Dome. This is one of the city’s most often recommended spots.

In the city of Florence, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

When 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.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

Day 8 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Della Signoria. This history-steeped public square is sure to ignite your curiosity. Next, dive into the noteworthy features of Bargello National Museum, a must-visit museum 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 Florence. There are so many fun and eye-opening activities to try out in Florence 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 Florence 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 dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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 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.

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

Start by visiting Piazza Del Duomo, Pisa, a prime spot to begin your journey. This breathtaking public square is sure to impress. Next on your list is Pisa Cathedral, another must-visit landmark and locally appreciated church renowned for its breathtaking features.

Leaning Tower Of Pisa also adds charm to your journey.

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

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Florence, explore the city like a local by trying out the best restaurants in the area.

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

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

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

On day 10 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Just a short distance away is Siena Cathedral, a visually striking church that draws visitors from far and near.

Continue your journey to Battistero Di San Giovanni Battista, one of the city’s most up-and-coming spots that you shouldn’t miss. Another great site to visit is the impressive Piazza Del Campo.

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

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.

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.

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

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Almalu Trastevere is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Viminale Di Pepi Maurilio offers an excellent atmosphere for those looking to amp up the evening.

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

At the top of the list of things to do today is to explore Monti, a neighborhood that captures the true essence of Rome. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions. Another must-visit is Via dei Condotti, a street offering a different perspective on Rome.

Rome is brimming with adventures. Today’s wonderful stops include a public square and an archeological site. Begin your sightseeing adventure at the world-famous Piazza Di Spagna. Just a short distance away is Colosseum, a historic archeological site that draws visitors from far and near.

Continue your journey to Roman Forum, one of the city’s most world-famous spots that you shouldn’t miss.

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, Rome 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 RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. With its reputation for pleasing customers, it’s a fantastic choice for tonight 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.

Continue your lively evening at Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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

On day 12 of your relaxed road trip across Italy, you’ll explore the area around Rome, where you’ll be staying for another 2 nights. With so many fun and inspiring experiences to offer, a tour of Rome will make you fall even more in love with the city and uniqueness of Italy.

At the top of the list of things to do today is to explore Trastevere, a neighborhood that captures the true essence of Vatican City. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. 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. St. Peter's Basilica is the first of them. Castel Sant'angelo is your next stop. This top-rated castle is one of the best-rated sights in Rome.

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 Piazza Navona. This symbolic public square is a sight to behold. To round off your sightseeing experience, visit Pantheon.

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.

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.

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

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

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!

Don’t miss Via del Corso in Rome today, a must-see street 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.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Altare Della Patria. This detailed monument is a highlight of any visit in the city. Then, enjoy Trevi Fountain, another masterful attraction that never fails to captivate visitors. Next, head over to Piazza Del Popolo, one of the city’s most spectacular attractions, known for its symbolic features.

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

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

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.

Have a fantastic dining experience at Sofitel Roma Villa Borghese, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Centro offers an enticing alternative with its varied menu. Additionally, Ristorante Tema 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.

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