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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Say hello to Milan! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Milan for 3 nights before you continue your adventure!

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.

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

After enjoying a fulfilling meal, continue your evening at Nottingham Forest, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Armani/bamboo Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Mag Cafe provides an excellent environment for a relaxed and enjoyable 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 of your road trip will take you to the best attractions Milan has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Milan.

Look forward to a unique sightseeing adventure at the iconic Duomo Di Milano Museum and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Vittorio Emanuele Ii, a visually striking shopping mall that draws visitors from far and near.

Continue your journey to La Scala, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the astonishing Sforzesco Castle Art Library. When you're finished at the castle, Parco Sempione awaits your visit. This park is a romantic highlight on today's itinerary. Last up is a monument - the popular Arch Of Peace.

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.

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

Have a fantastic dining experience at Dessert Bar Milano, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Radisson Blu Hotel Milan offers an enticing alternative with its varied menu. Additionally, Ristorante Qui Si Mangia is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

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

Relax and look forward to more memorable moments to come!

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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, Ossuccio. This car ride takes around 11 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co), an intriguing church that everyone visiting Ossuccio should see.

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.

Spend your afternoon discovering Villa Carlotta (lake Como), an underrated museum known for its visually striking features.

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

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

Enjoy a lovely dining experience at Bice Restaurant, 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 Alto Ristorante, 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 Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

Let the evening flow smoothly from dinner to drinks at Bhangrabar, a top-rated bar in the area. For other recommendations, Rufus Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Ostello Bello Grande offers a memorable night with diverse drink options and excellent service.

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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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

On day 4 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Throughout the day, make sure to take breaks to appreciate the surroundings.

Set your GPS to Florence and hit the road. Expect a journey of approximately 3 hours 31 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Florence beckons with new experiences!

Our first attraction recommendation in Florence is Basilica Of Santa Croce In Florence, a captivating church that draws attention for its culturally significant features. Spend some time soaking in the atmosphere before continuing to Uffizi Gallery, an eye-catching art gallery that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Ponte Vecchio, a world-famous historical landmark that offers a unique experience. Be sure to also explore Cathedral Of Santa Maria Del Fiore, a nearby church, highly recommended by other travelers. End your self-guided tour at Piazza Della Signoria, a noteworthy public square and the perfect final attraction in Florence.

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

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and celebrate another amazing day of your road trip 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

On day 5 of your road trip, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa and Lucca.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 1 hour 16 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Piazza Del Duomo, Pisa. Spend some time admiring the breathtaking features of the public square before you continue to your next stop. Then, head to Leaning Tower Of Pisa. This iconic monument is a traveler-favorite in the city.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Lucca. Expect your car journey to take a minimum of 32 min. When you arrive in Lucca, it's time to take a break from the road.

For a more meaningful self-guided tour of the city's best attractions, visit Guinigi Tower, a beloved 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 picture-perfect features.

When you’re ready, continue to Mura Di Lucca, an often recommended 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.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Rome may take around 3 hours 9 min. Upon your arrival in Rome, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready for some sights, head to Colosseum, a globally renowned archeological site in Rome. Explore its picture-perfect features at your own pace before you continue your journey to your next attraction, Roman Forum. This iconic 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 culturally significant monument in the region. Next, continue your sightseeing at the globally renowned Piazza Navona and discover what makes this public square unique.

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

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

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Continue the enjoyment post-dinner at La Botticella Of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Almalu Trastevere offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Viminale Di Pepi Maurilio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter 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

Your itinerary for day 7 of your road trip in Italy includes 2 stops and features some of the highlights of Rome and Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

Make time for Trevi Fountain, a globally renowned monument that is worthwhile a visit in the city. Nearby, you’ll find Piazza Di Spagna, enchanting visitors with its enchanting appeal. Continue your exploration at Spanish Steps. This public square is one of the city’s most widely recognized spots.

Fasten your seatbelt and make your way to your next stop — Bologna, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Bologna may take around 4 hours without traffic disruptions. Upon arrival in Bologna, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Fountain Of Neptune, Bologna, a curiosity-inducing monument in Bologna. Explore its photogenic features at your own pace before you continue your journey.

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.

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

Dine in style at Ristorante la Brisa, a top recommendation for dinner tonight. Or, for a change of pace, Pasticceria San Carlo boasts a menu that's sure to impress. Also, be sure to check out UNAHOTELS Cusani Milano. Known as a local hotspot, it’s a great choice for tonight in Milan.

Following your dinner, dive into the local bar culture at Qc Termemilano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yguana Cafè, the perfect place for those looking to experience the best of the nightlife.

As the sun sets, rest up and recharge for the next leg of your road trip 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 captivating public square is a hotspot among locals.

For a last-minute shopping spree in Milan, Galleria Vittorio Emanuele II is nearby. Enjoy a variety of retail stores, dining options, and essential services in one convenient location. 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.

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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