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!

Set aside time today to explore Navigli, 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.

Make a stop at Parco Sempione. This famous park is a must-visit for travelers looking for a unique holiday experience. Make your way to Sforzesco Castle Art Library located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Galleria Vittorio Emanuele Ii. Its noteworthy features will captivate you. After the shopping mall, continue your tour of the city with a visit to Duomo Di Milano Museum. Visitors usually appreciate the inviting features of this church.

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!

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 Dessert Bar Milano, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Radisson Blu Hotel Milan, 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 Ristorante Qui Si Mangia. It’s yet another ideal choice to enhance your time in Milan tonight.

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

To truly maximize your evening out, consider visiting Kilburn Cocktail Bar Milano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Frida, another bar with an inviting ambiance. Similarly, The Friends Pub Milano also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Free your mind of worries as you enjoy the taste of freedom on your laid-back 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.

To truly experience Milan, make sure to drop by Villa Del Balbianello. This worthwhile villa is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Villa Carlotta (lake Como), one of the village’s best highlights.

Next, check out Botanical Garden Of Villa Carlotta, one of the most frequently visited places to see in Milan. This botanical garden is a favorite among locals and travelers alike.

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.

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

Keep the evening going at Bhangrabar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Rufus Cocktail Bar, which offers a similarly pleasant setting and great drinks. Another option is Ostello Bello Grande, 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 4 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

No visit to Milan is complete without Verona Arena. This globally renowned stadium is one of the top attractions in the city. Proceed to Porta Borsari, another must-visit attraction.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Delle Erbe. This interesting public square is a traveler-favorite. Not far away, you’ll find Piazza Dei Signori, another key site on your sightseeing itinerary. Ponte Pietra is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

You'll be staying in Venice on this laid-back road trip through Italy. You'll stay here for 3 nights.

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

Enjoy a delicious meal at Bauer Hotel, a highly-rated dining destination in Venice. If you're eager to try something different, consider L'Osteria Le Guglie, another top spot with a tantalizing menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

After your 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.

Toast to another unforgettable and relaxing 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.

One of the most notable attractions included on the itinerary is Bridge Of Sighs. This history-steeped monument will help you start your sightseeing on top. Then, take a leisurely stroll to Doge's Palace and learn what makes this history-steeped palace unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the captivating St Mark's Basilica. After exploring the church, head to Piazza San Marco. This world-famous public square is a highlight in Venice. As your day continues, stop by Rialto Bridge, known for its visually striking features.

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 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.

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.

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.

Continue your evening by exploring the vibrant nightlife scene at Il Mercante, a prime destination for a thrilling night out. Also, don’t forget to check out The Irish Pub Venezia, a bar that offers unique local touches. Likewise, Ai Stagneri provides an excellent alternative for a fun 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!

Enjoy all that Palazzo Contarini Del Bovolo has to offer. This is an interesting palace you should not miss. Another must-see is Teatro La Fenice, a locally renowned opera house in Venice.

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

Italy makes the perfect setting for a calming but fun road trip experience. 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 Venice, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Dine in style at Osteria Alla Staffa, a top recommendation for dinner tonight. Or, for a change of pace, Bistrot de Venise boasts a menu that's sure to impress. Also, be sure to check out Corte Sconta. 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 Dolce Vita Venezia. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Tarnowska's American Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar All'angolo 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 7 of your relaxed road trip in 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!

Your adventure in Venice is only getting started when you visit Medici Chapels, a locally appreciated local hot spot. Another notable attraction to explore is Riccardi Medici Palace. This locally appreciated palace is known for its photogenic appeal.

After soaking in the highlights of these sights, take some time to wander Venice's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Brunelleschi's Dome. This history-steeped monument offers a fascinating experience that many visitors find memorable.

In Florence, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 8 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

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.

Make time for Piazza Della Signoria, an astonishing public square that is worthwhile a visit in the city. Nearby, you’ll find Bargello National Museum, enchanting visitors with its detailed 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 the food culture in Florence 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 delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, 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!

Your relaxed road trip in Italy continues on day 9 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Florence and beyond. With 1 night left in Florence, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

Catch Piazza Del Duomo, Pisa before the crowds roll in. This breathtaking public square is sure to ignite your curiosity. Next, dive into the symbolic features of Pisa Cathedral, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Angelo Caduto, a frequently visited point of interest. For a change of scene, check out Leaning Tower Of Pisa, known for its breathtaking features.

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.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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

Unwind after your meal by stepping into Gosh*. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Quelo Bar, another top-rated bar in the area.

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

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

Look forward to a unique sightseeing adventure at the beloved Fontan Kontradi Sel'va and allow yourself time to explore. Just a short distance away you'll find your next stop, Siena Cathedral, an inviting church that draws visitors from far and near.

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

Continue your laid-back road trip in Italy as you make your way to Rome. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

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.

Enjoy a lovely dining experience at La Bottega Roma, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Pasta In Corso, 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 Trattoria Vecchia Roma. It’s yet another ideal choice to enhance your time in Rome tonight.

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.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio 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 11 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Monti is one of the highlights of today. Take your time exploring this iconic neighborhood in Rome, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city. Be sure to also visit Via dei Condotti, a street that showcases another side of Rome.

Piazza Di Spagna is an ideal stop early in the day. This world-famous public square is a must-visit in the city. When you’re ready for your next discovery, continue to Colosseum, which may be one of the most historic places you will experience today.

One of the best things about exploring Rome 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 Roman Forum, an iconic archeological site 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 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 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.

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.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Sant' Eustachio Caffè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yellowsquare Rome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino is also a great option that provides a perfect setting for a relaxing evening.

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

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

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.

St. Peter's Basilica brings Rome's character to life. Then, enjoy Castel Sant'angelo, another history-steeped attraction that never fails to captivate visitors. Next, head over to Piazza Navona, one of the city’s most world-famous attractions, known for its romantic 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 the area’s best attractions, you’ll drive back to your accommodation in Rome.

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 delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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.

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

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

On day 13 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 1 night, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

Rome is brimming with adventures. Via del Corso is a street that stands out as one of the must-see places in Rome. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Your adventure in Rome is only getting started when you visit Altare Della Patria, a well-known local hot spot. Another notable attraction to explore is Trevi Fountain. This iconic 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 history-steeped 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.

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.

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.

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