5-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan and Florence

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Medieval and Renaissance buildings and structures feature in Bologna, Italy
Photo of panoramic view of Bologna,Italy.
5-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan and Florence
5-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan and Florence
5-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan and Florence
5-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan and Florence
5-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan and Florence
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Escape the ordinary with this exciting 5-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Bologna, 1 night in Milan, and 1 night in Florence. 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 Bologna, 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. Duomo Di Milano Museum and Ponte Vecchio are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Bologna, Milan, Parma, and Florence, 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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Pick-up: 10:00
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Day1

Day 1

  • Bologna - Arrival day
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  • Piazza Maggiore
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Welcome to Bologna, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night discovering what to see in Bologna before embarking on the next leg of your journey.

Bologna 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 Piazza Maggiore. 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.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Bologna. Make yourself at home and unwind before heading out again.

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 Bologna, it's often a good idea to reserve a table in advance.

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

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise a toast to the start of your 5-day road trip in Italy!

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Day2

Day 2

  • Bologna
  • Milan
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Drive 224 km, 2 hours 59 min

  • Basilica of San Domenico
  • Piazza Santo Stefano
  • Two Towers
  • Ducati Museum
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Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Milan, where will spend 1 night.

Basilica Of San Domenico leaves a lasting impression. This church is one of the most locally appreciated places to visit in Bologna. Next, head to Piazza Santo Stefano, a beloved public square, known for its enchanting features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Two Towers. This stunning monument is a highly recommended experience. Nearby, you'll also find Ducati Museum Visit these for an interesting touch to your journey.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. 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 Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the evening going at Nottingham Forest, a great choice for enjoying the after-dinner hours with a drink. You could also go to Armani/bamboo Bar, which offers a similarly pleasant setting and great drinks. Another option is Mag Cafe, which provides an inviting environment for unwinding after a busy day out.

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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Day3

Day 3

  • Milan
  • Parma
  • Florence
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Drive 331 km, 4 hours 9 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Parma Cathedral
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On day 3 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Milan and Parma are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Visiting Duomo Di Milano Museum is always a good idea. This globally renowned church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Galleria Vittorio Emanuele Ii, a must-see shopping mall in the city.

Embrace the thrill of the open road as you wave goodbye to Milan and set your GPS to Parma. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 37 min. Upon reaching Parma, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

For a more meaningful self-guided tour of the city's best attractions, visit Parma Cathedral, a locally appreciated church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring 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 Florence. Florence 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and recharge in preparation for another adventurous day in Italy!

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Day4

Day 4

  • Florence
  • Bologna
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Drive 110 km, 2 hours 12 min

  • piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Uffizi Gallery
  • piazzale Michelangelo
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Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Piazza Della Signoria is an ideal stop early in the day. This astonishing public square is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most UNESCO world heritage-designated 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 Ponte Vecchio, a globally renowned historical landmark in the city. If you’re up for more discoveries, don’t forget to reserve some time for Uffizi Gallery and Piazzale Michelangelo.

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

Bologna 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 Bologna.

Set out on a gastronomic journey in Bologna by reserving a table at Ahimè. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of country cooking cuisine. For a different taste, head over to I Portici, renowned for its delectable creative and contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss.

Unwind after your meal by stepping into Lime Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Macondo - Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Onda Marina By Night, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!

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Day5

Day 5

  • Bologna - Departure day
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  • arco del Meloncello
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Day 5 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Bologna 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, we recommend visiting Arco Del Meloncello, a breathtaking monument before you head out.

For a shopping spree in Bologna, we recommend the lively Quadrilatero. Here, you'll find a range of shops you can browse for some souvenir shopping. Discover boutiques with stylish fashion choices to upgrade your wardrobe.

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

If you're in the mood for something new, try Trattoria dal Biassanot, another premier location with a delectable menu.

You’ll then say farewell to Bologna. 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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