One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence and Rome

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Milan Cathedral, Duomo di Milano, and Piazza Duomo square in the Milan city center, Italy
Photo of Arch of Peace, or Arco della Pace, city gate in the centre of the Old Town of Milan in the sunny day, Lombardia, Italy.
One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence and Rome
One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence and Rome
One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence and Rome
One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence and Rome
One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence and Rome
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Experience the freedom of the open road on an unforgettable 8-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Milan, Lenno, Ossuccio, Florence, Pisa, Lucca, Rome, and Bologna.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 4 nights in Milan, 2 nights in Florence, and 1 night in Rome. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have you covered.

Upon arriving in Milan, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Milan, Lenno, Ossuccio, Florence, Pisa, Lucca, Rome, and Bologna, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodations, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Driver’s age is 30 - 65
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Day1

Day 1

  • Milan - Arrival day
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  • Pinacoteca di Brera
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Your road trip adventure in Italy begins as soon as you reach Milan and pick up your car. You’ll stay here for 3 nights and explore what to see in Milan, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Milan is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Pinacoteca Di Brera. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Milan. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a central location for easy access to key areas in the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Milan, it's often a good idea to reserve a table in advance.

Savor the flavors at Hotel Morfeo Milano, a top pick for dinner tonight. Alternatively, Contraste beckons with its unique menu offerings. Also, consider UNAHOTELS Galles Milano. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

Continue your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun evening.

Raise a toast to the start of your 8-day road trip in Italy!

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Day2

Day 2

  • Milan
  • More

Drive 5 km, 50 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • La Scala
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • More

Day 2 offers an itinerary packed with the best things to see in Milan. You’ll stay in Milan for 2 nights more, offering you enough time to explore at a relaxed pace.

Experience Duomo Di Milano Museum, a globally renowned church in the city. Then, head to Galleria Vittorio Emanuele Ii and soak in the ambiance of this history-steeped shopping mall.

There are many interesting places to see in Milan, and when you are ready for more, go to La Scala. This is one of the city’s most captivating standout spots of interest. After exploring the opera house, visit the famous Sforzesco Castle Art Library. Not far away, you'll also find Parco Sempione. This park is a mesmerizing highlight in Milan. Before wrapping up your self-guided sightseeing tour, head to Arch Of Peace, a popular monument in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Milan, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Dessert Bar Milano, an excellent option for tonight's dining. Looking for something different? Radisson Blu Hotel Milan offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Qui Si Mangia. Known for great service, it’s a fantastic choice for tonight in Milan.

After enjoying a fulfilling meal, continue your evening at Kilburn Cocktail Bar Milano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Frida offers a welcoming atmosphere for easing into the nightlife. Similarly, The Friends Pub Milano provides an excellent environment for a relaxed and enjoyable evening.

Head back to your accommodation in Milan and get some rest to prepare for another magical day of your road trip in Italy.

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Day3

Day 3

  • Milan
  • Lenno
  • Ossuccio
  • More

Drive 227 km, 4 hours 15 min

  • Villa del Balbianello
  • Sacro Monte della Beata Vergine del Soccorso - Ossuccio (co)
  • Villa Carlotta
  • More

On day 3 of your road trip in Italy, you’ll start and end your day in Milan, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Milan, there’s no need to rush. Experience Lenno, Ossuccio, and Rogaro to the fullest today with this curated day itinerary.

Continue your road trip and head to your next destination, Lenno. This car ride takes around 1 hour 25 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Villa Del Balbianello, a frequently visited villa that everyone visiting Lenno should see.

When you’re ready to jump back into the car and say goodbye to Lenno, you’ll hit the road in the direction of Ossuccio. This drive usually takes around 11 min.

When you're ready for some sights, head to Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co), an often recommended church in Ossuccio. Explore its visually striking features at your own pace before you continue your journey.

Rogaro’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Ossuccio behind. This drive usually takes around 12 min. Rogaro welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Villa Carlotta (lake Como). Spend some time admiring the romantic features of the museum before you continue to your next stop.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Milan, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bhangrabar, known for its inviting atmosphere. Rufus Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Ostello Bello Grande provides a great setting to enjoy the night away.

Savor another day of unforgettable experiences in Italy!

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Day4

Day 4

  • Milan
  • Florence
  • More

Drive 309 km, 3 hours 59 min

  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • More

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Florence. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 2 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Florence may take around 3 hours 31 min. Upon your arrival in Florence, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Basilica Of Santa Croce In Florence is a locally renowned church we recommend visiting today. Discover its culturally significant features before continuing your self-guided tour to Uffizi Gallery, a romantic art gallery that’s well-regarded in the area.

Next, stop by Ponte Vecchio, an enchanting historical landmark. While you’re nearby, don’t forget to visit Cathedral Of Santa Maria Del Fiore, a culturally significant and truly unique church. End your sightseeing at Piazza Della Signoria, a famous public square that’s highly recommended by travelers passing through the city.

At the end of the day, you will drive to Florence, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

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.

Savor another day of unforgettable experiences in Italy!

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Day5

Day 5

  • Florence
  • Pisa
  • Lucca
  • More

Drive 196 km, 3 hours 14 min

  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Guinigi Tower
  • San Michele in Foro
  • Walls of Lucca
  • More

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Pisa and Lucca.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 16 min.

When you're ready for some sights, head to Piazza Del Duomo, Pisa, a world-famous public square in Pisa. Explore its breathtaking features at your own pace before you continue your journey to your next attraction, Leaning Tower Of Pisa. This timeless monument is a top recommendation in the area.

Lucca’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 32 min. Lucca welcomes you with a multitude of unique vacation experiences.

For a more meaningful self-guided tour of the city's best attractions, visit Guinigi Tower, a curiosity-inducing monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to San Michele In Foro and admire its symbolic features.

When you’re ready, continue to Mura Di Lucca, an up-and-coming historical landmark beloved by locals and tourists alike.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

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. Known for great service, it’s a fantastic choice for tonight in Florence.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day6

Day 6

  • Florence
  • Rome
  • More

Drive 279 km, 3 hours 57 min

  • Colosseum
  • Roman Forum
  • Pantheon
  • Piazza Navona
  • More

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 1 night.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Rome. Your travel time is around 3 hours 9 min.

When you're ready for some sights, head to Colosseum, a timeless archeological site in Rome. Explore its historic features at your own pace before you continue your journey to your next attraction, Roman Forum. This globally renowned archeological site is a top recommendation in the area.

When you’re ready to explore more, Pantheon is an excellent choice. Spend some time discovering what some claim to be the most inviting monument in the region. Next, continue your sightseeing at the timeless Piazza Navona and discover what makes this public square unique.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and relax before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day7

Day 7

  • Rome
  • Bologna
  • Milan
  • More

Drive 591 km, 6 hours 49 min

  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • Fountain of Neptune, Bologna
  • More

On day 7 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Rome and Bologna are on today's agenda. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Visiting Trevi Fountain is always a good idea. This world-famous monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Piazza Di Spagna, a must-see public square 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 Spanish Steps. This impressive public square offers an enriching experience.

Bologna’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 4 hours. Bologna welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Fountain Of Neptune, Bologna, an underrated monument that draws visitors from near and far.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a day of adventure, treat yourself to an exquisite dinner at one of Milan's best restaurants.

Have a fantastic dining experience at Ristorante la Brisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasticceria San Carlo offers an enticing alternative with its varied menu. Additionally, UNAHOTELS Cusani Milano is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Qc Termemilano stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yguana Cafè offers an ideal atmosphere to enjoy the pleasures of the night.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day8

Day 8

  • Milan - Departure day
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  • Piazza Gae Aulenti
  • More

Day 8 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Milan before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, begin at Piazza Gae Aulenti. This interesting public square is a hotspot among locals.

For a last-minute shopping spree in Milan, Quadrilatero della Moda is nearby. Enjoy a variety of retail stores, dining options, and essential services in one convenient location. Browse through boutiques to find unique and stylish fashion pieces to take home. Explore high-end stores offering an exquisite selection of luxury items.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Milan.

Treat yourself to a delightful dinner at Vento di Sardegna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Palazzo Parigi Hotel & Grand Spa Milano? It's another excellent option with a diverse menu.

You’ll then say farewell to Milan. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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