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.

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.

Today’s itinerary in Milan covers several incredible sights, including a park, a castle, a shopping mall, a church and much more! Start your adventure at Parco Sempione. This spectacular park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the breathtaking wonders of Sforzesco Castle Art Library, a must-see castle 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 Galleria Vittorio Emanuele Ii. This top-rated shopping mall offers an enriching experience. For a change of pace, head to Duomo Di Milano Museum, where you can take in enchanting features. These sights offer a fulfilling end to a perfect day.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Milan. There are so many fun and eye-opening activities to try out in Milan that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Milan to find the best options for you!

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.

Don’t miss out on dining at Dessert Bar Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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

Explore the vibrant nightlife at Kilburn Cocktail Bar Milano after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Frida for a great selection of flavorful drinks and a charming setting. Furthermore, The Friends Pub Milano is perfect for those looking to extend their night with a touch of local flavor.

Cherish every minute of your relaxed road trip vacation across 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.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most often recommended attractions included on the itinerary is Villa Del Balbianello. Then, take a leisurely stroll to Villa Carlotta (lake Como) and learn what makes this visually striking museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile Botanical Garden Of Villa Carlotta.

When you’re done exploring for the day, you’ll return to Milan 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 Milan, explore the city like a local by trying out the best restaurants in the area.

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu. You could also check for a table at Nero 9. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan 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.

Cap off your dinner by heading to Bhangrabar, ideal for a leisurely evening with a drink in hand. Rufus Cocktail Bar is another bar that offers an enjoyable setting. Similarly, Ostello Bello Grande 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!

On day 4 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.

Start by visiting Verona Arena, a prime spot to begin your journey. This enchanting stadium is sure to impress. Next on your list is Porta Borsari, another must-visit landmark and curiosity-inducing historical landmark renowned for its symbolic 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 Piazza Delle Erbe. This romantic public square is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Piazza Dei Signori, an often recommended public square. Nearby, you'll also find Ponte Pietra, ready to add charm to your journey.

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

Treat yourself to a delicious dinner at Bauer Hotel, an excellent option for tonight's dining. Looking for something different? L'Osteria Le Guglie offers a tantalizing alternative with its diverse menu. And don’t miss Corner Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

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 Venice. The bars in Venice make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Continue your evening by exploring the vibrant nightlife scene at Al Parlamento, a prime destination for a thrilling night out. Also, don’t forget to check out The Caffe Rosso, a bar that offers unique local touches. Likewise, Adagio provides an excellent alternative for a fun evening.

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

On day 5 of your leisurely self-drive tour across Italy, you’ll go deep into Venice, 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 Venice, and meet locals along the way!

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Venice on today’s itinerary. First up is the notable 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 locally renowned 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, an iconic historical landmark in the city.

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

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.

Treat yourself to a delightful dinner at Generator Venice, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Nevodi? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante La Piazza as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

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.

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

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 captivating palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Teatro La Fenice located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Peggy Guggenheim Collection. Its detailed features will captivate you. After the art gallery, continue your tour of the city with a visit to Santa Maria Della Salute. Visitors usually appreciate the enchanting features of this 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 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.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Dolce Vita Venezia is an excellent place to start. You could also check out Tarnowska's American Bar, offering a different kind of charm. A last recommendation for the day is Bar All'angolo. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

Day 7 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 Florence. By the end of the day, you’ll drive in the direction of the city of Florence, where you’ll stay at a top-rated hotel of your choice for 3 nights.

Discover a day packed with family-friendly attractions, picturesque spots, and history-rich sites in Venice. Begin your sightseeing with Medici Chapels. This underrated museum is one of the top attractions in the city. Proceed to Riccardi Medici Palace, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Brunelleschi's Dome. This frequently visited monument is a traveler-favorite.

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.

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 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.

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

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

A top thing to do today is to explore Oltrarno, a must-see neighborhood in Florence. It's the perfect starting point for touring the top attractions in the area.

Today’s agenda in Florence includes a public square and a museum. Piazza Della Signoria is must-visit public square and a great starting point for the day. Next, continue your journey to Bargello National Museum, an up-and-coming museum, located just a leisurely stroll away.

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.

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 Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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.

Florence is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and picturesque spots! Start at Piazza Del Duomo, Pisa, a globally renowned public square that is worthwhile a visit in the city. Nearby, you’ll find Pisa Cathedral, enchanting visitors with its UNESCO world heritage-designated appeal. Continue your exploration at Angelo Caduto. This point of interest is one of the city’s most increasingly popular spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Leaning Tower Of Pisa.

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

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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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

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

Soak in the unique atmosphere of Florence 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!

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

Start your day with a visit to Fontan Kontradi Sel'va. This curiosity-inducing sightseeing destination is a must-visit in the city. When you’re ready for your next discovery, continue to Siena Cathedral, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Florence 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 Battistero Di San Giovanni Battista, an intriguing church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Del Campo.

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.

Exploring the food culture in Rome offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

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.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 3 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 Rome, and meet locals along the way!

Monti is a fantastic place you can explore today in Rome. 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 Rome-way-of-life and visit all the nearby sights. You should also check out Via dei Condotti, a street offering more opportunities to enjoy the city’s vibrant atmosphere and landmarks.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazza Di Spagna. This timeless public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Colosseum, one of the city’s best highlights.

Next, check out Roman Forum, one of the most iconic places to see in Rome. This archeological site is a favorite among locals and travelers alike.

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.

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

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

To truly maximize your evening out, consider visiting Sant' Eustachio Caffè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yellowsquare Rome, another bar with an inviting ambiance. Similarly, Caffè Portofino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Set aside time today to explore Trastevere, 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to St. Peter's Basilica. This world-famous major basilica provides an insightful glimpse into the city's identity. Next, discover Castel Sant'angelo, a visually striking castle, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Navona, an iconic public square. When you’re done, don’t forget to make a stop at the globally renowned Pantheon.

When you’re done exploring for the day, you’ll return to Rome 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 Rome, 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 Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. 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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

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

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!

One of the most iconic places you can visit today in Rome is Via del Corso. Allow yourself some time to explore this street and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Get ready for a day filled with family-friendly attractions, scenic views, and picturesque spots in the charming city of Rome. Your adventure starts at Altare Della Patria, a well-known local hot spot. Another notable attraction to explore is Trevi Fountain. This timeless monument is known for its breathtaking 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 Piazza Del Popolo. This culturally significant public square offers a fascinating experience that many visitors find memorable. Villa Borghese is also worth visiting.

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 Rome, 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 Sofitel Roma Villa Borghese, 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 Centro, 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 Ristorante Tema, 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.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!