Luxury 6-Day Italy Road Trip from Bologna traveling west to Milan, Genoa, and Florence

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Experience travel that redefines comfort and elegance with this 6-day luxury road trip in Italy. Witness Italy's awe-inspiring scenery, delight in the finest culinary offerings, and enjoy the ultimate comfort in top-tier accommodations.

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned vacation itinerary, you will stay 2 nights in Bologna, 1 night in Milan, 1 night in Genoa, and 1 night in Florence, experiencing the ultimate luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 6-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.

Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 6-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.

Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. Here you can find unique souvenirs to preserve the memory of your luxury holiday in Italy.

This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 6-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.

To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Bologna, Milan, Genoa, Pisa, and Florence at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best flights, activities, tours, and hotels in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your luxury holiday in Italy today!

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Day 1

Day 1 – Bologna - arrival day

  • Bologna - Arrival day
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  • Arco Del Meloncello
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Your luxury holiday in Italy begins as soon as you reach the city of Bologna. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Kick off the day at Arco Del Meloncello, a top pick for today’s sightseeing. This arch is rated an average of 4.6 out of 5 stars in 3,755 reviews.

Tonight, you will be treated to a stay at one of the best luxury hotels in Bologna. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Bologna so you can check out the menus and make advance reservations.

Don’t miss out on dining at Sfoglia Rina, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Va Mo Là, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria dal Biassanot. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Bologna this evening.

Keep the evening going at Bar Freud E Squisito, a great choice for enjoying the after-dinner hours with a drink. You could also go to Osteria Del Sole, which offers a similarly pleasant setting and great drinks. Another option is Macondo - Cocktail Bar, which provides an inviting environment for unwinding after a busy day out.

Raise a toast to the start of your 6-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Bologna, and Milan

  • Milan
  • Bologna
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Drive 223 km, 2 hours 49 min

  • Cattedrale Metropolitana di San Pietro
  • Fontana del Nettuno
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna. The day's journey will conclude in Milan, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Drop by the renowned Bologna Cathedral. This popular catholic cathedral has been rated an average of 4.6 out of 5 stars by 3,852 visitors.

Another unforgettable place to experience is Fountain Of Neptune, Bologna. Rated 4.7 out of 5 stars by 3,952 visitors, this fountain deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Piazza Maggiore. This square has been rated an average of 4.7 out of 5 stars in 64,523 reviews.

Another favorite attraction in the area is Two Towers. This tower and popular place of interest enjoys a rating of 4.7 out of 5 stars from 25,975 local and international travelers.

If you’re keen to explore even more, then consider a visit to Piazza Santo Stefano. With an average rating of 4.8 out of 5 stars from 7,617 travelers, this square is an attraction many avid travelers highly recommend visiting while in Bologna.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Milan.

Enjoy an outstanding dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an exceptional creative menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Seta by Antonio Guida, known for its delicious international, and contemporary cuisine. Another highly-recommended restaurant in Milan is Il Luogo Aimo e Nadia, a renowned restaurant with a 1-star Guide Michelin recognition, known for its delicious italian contemporary, and modern menu.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Nottingham Forest stands out as an excellent choice for a post-dinner cocktail. Alternatively, Armani/bamboo Bar offers an ideal atmosphere to enjoy the pleasures of the night. Mag Cafe is also a great option that provides a perfect setting for a relaxing evening.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

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Day 3

Day 3 – Milan, and Genoa

  • Genoa
  • Milan
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Drive 153 km, 2 hours 42 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Sforzesco Castle
  • Sempione Park
  • Piazza Gae Aulenti
  • More

Wake up to day 3 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Genoa, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Milan.

Start your sightseeing with a visit to Duomo Di Milano Museum. This art museum is rated an average of 4.8 out of 5 stars from 138,554 visitors. Duomo Di Milano Museum welcomes around 341,609 visitors every year.

Galleria Vittorio Emanuele Ii is another popular attraction you could visit today. This commercial gallery has a rating of 4.7 out of 5 stars from 91,394 visitors.

Sforzesco Castle Art Library is also highly recommended by travelers. This library has a rating of 4.6 out of 5 stars from 68,714 visitors.

Parco Sempione is an attraction you won’t want to miss. This park is rated an average of 4.6 out of 5 stars in 72,914 reviews.

Another attraction you have the opportunity to visit today is Piazza Gae Aulenti. This square has received an average rating of 4.6 out of 5 stars from 30,398 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Genoa. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

In Genoa, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.

Dive into a culinary adventure like no other in Genoa by booking a table at The Cook. This popular restaurant holds 1 Michelin star and offers an exceptional menu of modern cuisine. For another culinary dining option, venture to San Giorgio, celebrated for its delectable modern, and ligurian menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Il Marin, a top local restaurant known for its tantalizing seafood, and contemporary menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Extend your evening after a delightful meal by visiting Scurreria Beer & Bagel, which offers the perfect atmosphere for a night out. Moreover, La Lepre is another popular option for a drink or two.

Raise your glass and relax after another big day of your luxury holiday in Italy!

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Day 4

Day 4 – Genoa, Pisa, and Florence

  • Florence
  • Genoa
  • Pisa
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Drive 268 km, 3 hours 48 min

  • Piazza De Ferrari
  • Aquarium of Genoa
  • Piazza del Duomo
  • Leaning Tower of Pisa
  • More

Wake up to day 4 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Genoa, and Pisa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Journey into the unknown at Piazza De Ferrari, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.6 out of 5 stars from 34,312 reviews.

When you’re ready to continue your sightseeing, Aquarium Of Genoa is a recommended place to visit. This public aquarium is rated an average of 4.5 out of 5 stars in 62,259 reviews. Based on recent data, the attraction hosts 1,200,000 visitors per year.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 2 hours 3 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Seize the day by visiting some of the best attractions in the area, like Piazza Del Duomo, Pisa. This extraordinary square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Next, make your way to Leaning Tower Of Pisa. This bell tower welcomes around 3,200,000 visitors yearly and is rated an average of 4.7 out of 5 stars in 116,882 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Florence so you can check out the menus and make advance reservations.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative, and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary, and international cuisine in the city.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Raise a toast to another amazing day of your luxury holiday in Genoa, Italy and seize the opportunity to celebrate.

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Day 5

Day 5 – Florence, and Bologna

  • Bologna
  • Florence
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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
  • More

On day 5 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence. The day's journey will conclude in Bologna, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

When you're ready to see some sights, Piazza Della Signoria is a great place to start. This square is rated an average of 4.8 out of 5 stars by 66,956 visitors.

Another popular attraction you can visit today is Cathedral Of Santa Maria Del Fiore. This church has an average rating of 4.8 out of 5 stars from 76,359 travelers.

We also recommend a stop at Ponte Vecchio. The deck arch bridge has been rated an average of 4.7 out of 5 stars by 118,099 visitors.

If you're keen to explore more, consider visiting Uffizi Gallery. This national museum is a popular attraction with an average rating of 4.7 out of 5 stars from 61,794 reviews. As a top-rated attraction, it's no surprise that 2,011,219 people visit Uffizi Gallery every year.

Piazzale Michelangelo is another easily accessible place to visit on this day of your trip. Stop by this square, rated 4.8 out of 5 stars in 77,744 reviews, to discover more of what makes it unique.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Bologna. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Bologna.

Prepare for an extraordinary culinary adventure in Bologna by booking a table at I Portici, a 1-star Michelin restaurant that boasts an exceptional creative, and contemporary menu. For a different flavor experience, head to Ahimè, renowned for its delectable country cooking dishes. This Bib Gourmand restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Trattoria di Via Serra, a local gem known for its delightful emilian cuisine in Bologna. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

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

Reminisce about your day, look through photos, and prepare for another great day to come! Your luxury holiday in Italy has plenty more in store for you.

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Day 6

Day 6 – Bologna - departure day

  • Bologna - Departure day
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Today is the last day of your 6-day luxury holiday in Italy and it’s soon time to start your journey home. This is your chance to get one last glimpse of Bologna before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Bologna’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Make the most of what's left of your luxury vacation and head out to the stunning Porta Maggiore. This extraordinary landmark and attraction is rated an average of 4.4 out of 5 stars in 1,462 reviews, and is an excellent choice for your last sightseeing in Bologna.

Treat yourself to a final feast. Savor the unique flavors of Bologna one last time before you head to the airport.

Treat yourself to a delightful dinner at Trattoria del Tempo Buono, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Cantina Bentivoglio? It's another excellent option with a diverse menu.

You will then say farewell to Bologna and begin your journey home. We wish you safe travels and a warm welcome home, with unforgettable memories and incredible photos from your luxury holiday in Italy in your luggage!

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