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 the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. 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 got 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. Marvel at the remarkable Galleria Vittorio Emanuele Ii, learn more about the unique Piazzale Michelangelo, and immerse yourself in the vibrant atmosphere of Cathedral Of Santa Maria Del Fiore.

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, accommodation, 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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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Piazza Maggiore
Basilica of San DomenicoPiazza Santo StefanoTwo TowersDucati Museum
Duomo di MilanoGalleria Vittorio Emanuele IIParma Cathedral
piazza della SignoriaCathedral of Santa Maria del FiorePonte VecchioUffizi Gallerypiazzale Michelangelo
arco del Meloncello

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Day 1

Day 1

  • Bologna - Arrival day
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  • Piazza Maggiore
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Say hello to Bologna! 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 Bologna for 1 night before you continue your adventure!

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, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Bologna. Make yourself at home and enjoy some downtime 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.

Enjoy a lovely dining experience at Ristorante Ciacco, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Ristorante Ballarini, 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 Sfoglia Rina. It’s yet another ideal choice to enhance your time in Bologna tonight.

Extend your evening after a delightful meal by visiting Bar Al Bricco D'oro, which offers the perfect atmosphere for a night out. Moreover, Bar Freud E Squisito is another popular option for a drink or two. Likewise, Osteria Del Sole also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 2

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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On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Milan, where you’ll be staying for 1 night.

Today’s agenda in Bologna includes a church, a public square, a monument, a museum and much more! Basilica Of San Domenico is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Santo Stefano, an increasingly popular public square, located just a leisurely stroll away. Next, head to Two Towers, a historic monument, also available for your discovery today.

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

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 and reflect on the day's adventures.

Experience a harmony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Known for its 3-star Michelin status, Enrico Bartolini al Mudec offers a delightful variety of dishes highlighting its delicious creative menu. If you're seeking an alternative culinary experience, be sure to explore Seta by Antonio Guida, a highly recommended restaurant known for its enticing international and contemporary cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Il Luogo Aimo e Nadia, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and modern menu.

Continue your lively evening at Nottingham Forest, a perfect place for winding down or revving up the night, depending on which mood you’re in. Armani/bamboo Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Mag Cafe ensures a night out tailored to your taste.

Say good night to Milan and look forward to another great day of your road trip in Italy!

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Day 3

Day 3

  • Milan
  • 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, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Milan and Parma. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Milan. Begin your sightseeing with Duomo Di Milano Museum. This world-famous church is one of the top attractions in the city. Proceed to Galleria Vittorio Emanuele Ii, 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 Parma Cathedral. This frequently visited church is a traveler-favorite.

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

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

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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night 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 in Italy.

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Day 4

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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Dive into day 4 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna. You’ll stay here for 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a public square, a church, a historical landmark, an art gallery, an observation deck and much more! Begin your adventure at Piazza Della Signoria. This is a top-rated public square you should not miss. Another must-see is Cathedral Of Santa Maria Del Fiore, a widely recognized church in Florence.

When you’re ready for the next sight, head to Ponte Vecchio. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s astonishing attractions. We recommend continuing your self-guided tour at Piazzale Michelangelo, a visually striking place of interest in the city.

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

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

Experience a taste of local culinary excellence while in Bologna by securing a table at Ahimè. An esteemed Bib Gourmand restaurant, it features an exceptional country cooking menu. For an alternative taste experience, visit I Portici, famous for its scrumptious creative and contemporary dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Lime Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Macondo - Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Bar Onda Marina By Night is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 5

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, begin at Arco Del Meloncello. This beloved monument is a popular place to see in the city.

Make the most of your final day in Italy by visiting Bologna’s iconic markets and shopping establishments in the buzzing Galleria Cavour. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. Elevate your style with pieces from high-end retail stores.

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

Dine in style at Va Mo Là, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria dal Biassanot boasts a menu that's sure to impress.

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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