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!

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.

Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a park, a castle, a shopping mall, a church and much more! Begin your adventure at Parco Sempione. This is a top-rated park you should not miss. Another must-see is Sforzesco Castle Art Library, a famous castle in Milan.

When you’re ready for the next sight, head to Galleria Vittorio Emanuele Ii. From there, take a leisurely stroll to Duomo Di Milano Museum, another of the city’s world-famous attractions.

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.

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.

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.

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.

Continue your lively evening at Kilburn Cocktail Bar Milano, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Frida is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, The Friends Pub Milano ensures a night out tailored to your taste.

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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Milan allows for both. Start by heading to Villa Del Balbianello. This beloved villa provides an insightful glimpse into the village's identity. Next, discover Villa Carlotta (lake Como), an enchanting museum, promising a delightful encounter.

Continue your sightseeing with a visit to Botanical Garden Of Villa Carlotta, an increasingly popular botanical garden.

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.

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

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

Day 4 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Venice for 3 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.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most timeless attractions included on the itinerary is Verona Arena. This visually striking stadium will help you start your sightseeing on top. Then, take a leisurely stroll to Porta Borsari and learn what makes this instagrammable historical landmark unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the interesting Piazza Delle Erbe. After exploring the public square, head to Piazza Dei Signori. This beloved public square is a highlight in Milan. As your day continues, stop by Ponte Pietra, known for its enchanting features.

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.

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.

Dine in style at Bauer Hotel, a top recommendation for dinner tonight. Or, for a change of pace, L'Osteria Le Guglie boasts a menu that's sure to impress. Also, be sure to check out Corner Pub. Known as a local hotspot, it’s a great choice for tonight in Venice.

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.

Keep the evening going at Al Parlamento, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Caffe Rosso, which offers a similarly pleasant setting and great drinks. Another option is Adagio, which provides an inviting environment for unwinding after a busy day out.

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

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

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Bridge Of Sighs. This captivating monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Doge's Palace, one of the city’s best highlights.

Next, check out St Mark's Basilica, one of the most notable places to see in Venice. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza San Marco. Wander around and soak in the majestic atmosphere this public square offers. Then, head to Rialto Bridge, a top-rated historical landmark that adds another dimension to your day.

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 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 Generator Venice, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Nevodi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante La Piazza. 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.

Keep the evening going at Il Mercante, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Irish Pub Venezia, which offers a similarly pleasant setting and great drinks. Another option is Ai Stagneri, which provides an inviting environment for unwinding after a busy day out.

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

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!

Today, you'll explore some of the most beautiful places in Venice, including a palace, an opera house, an art gallery, a church and much more! Start your day with a visit to Palazzo Contarini Del Bovolo. This notable palace is a must-visit in the city. When you’re ready for your next discovery, continue to Teatro La Fenice, which may be one of the most romantic places you will experience today.

One of the best things about exploring Venice 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 Peggy Guggenheim Collection, a notable art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Santa Maria Della Salute.

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 Osteria Alla Staffa, a top pick for dinner tonight. Alternatively, Bistrot de Venise beckons with its unique menu offerings. Also, consider Corte Sconta. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

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.

Cap off your dinner by heading to Dolce Vita Venezia, ideal for a leisurely evening with a drink in hand. Tarnowska's American Bar is another bar that offers an enjoyable setting. Similarly, Bar All'angolo is also a popular place to go on a night out, perfect for relaxing and socializing.

Grab a drink and enjoy every passing minute of this night of your 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!

Today’s agenda in Venice includes a museum, a palace, and a monument. Medici Chapels is must-visit museum and a great starting point for the day. Next, continue your journey to Riccardi Medici Palace, an underrated palace, located just a leisurely stroll away. Next, head to Brunelleschi's Dome, a history-steeped monument, also available for your discovery today.

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.

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.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect 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 delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, 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!

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.

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.

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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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.

Today’s route brings fun adventures, scenic views, and photo-friendly spots. The first attraction of today is Piazza Del Duomo, Pisa. This wondrous public square is a stunning place to see in Florence. Continue your discovery at Pisa Cathedral, a picture-perfect church with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Angelo Caduto. Next, make your way to Leaning Tower Of Pisa 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 Florence.

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.

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

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

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

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

Day 10 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 Siena. By the end of the day, you’ll drive in the direction of the city of Rome, where you’ll stay at a top-rated hotel of your choice for 4 nights.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Next, go to Siena Cathedral.

After visiting Fontan Kontradi Sel'va and Siena Cathedral, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Battistero Di San Giovanni Battista. This photogenic church offers a unique experience. Piazza Del Campo is another noteworthy attraction worthwhile a visit.

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.

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 Rome, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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.

Let the evening flow smoothly from dinner to drinks at La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Almalu Trastevere provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Viminale Di Pepi Maurilio offers a memorable night with diverse drink options and excellent service.

Grab a drink and enjoy every passing minute of this night 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.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming city of Rome. Your adventure starts at Piazza Di Spagna, a timeless local hot spot. Another notable attraction to explore is Colosseum. This iconic archeological site is known for its visually striking appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Roman Forum. This historic archeological site offers a fascinating experience that many visitors find memorable.

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.

Make sure to reserve a table at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, 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.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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

Start your adventure at St. Peter's Basilica. This world-famous major basilica is a must-visit for travelers looking for a unique holiday experience. Make your way to Castel Sant'angelo located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Piazza Navona. Its visually striking features will captivate you. After the public square, continue your tour of the city with a visit to Pantheon. Visitors usually appreciate the monumental features of this monument.

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.

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

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.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across 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!

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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Altare Della Patria. This interesting monument provides an insightful glimpse into the city's identity. Next, discover Trevi Fountain, a history-steeped monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Del Popolo, a widely recognized public square. When you’re done, don’t forget to make a stop at the spectacular Villa Borghese.

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 Rome.

Treat yourself to a wonderful meal at Sofitel Roma Villa Borghese, a top-rated dining spot in Rome. If you're in the mood for something new, try Centro, another premier location with a delectable menu. You might also want to book a table at Ristorante Tema. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

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

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