Luxury 9-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 9-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, 2 nights in Milan, 2 nights in Genoa, and 2 nights 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 9-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 9-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 9-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
  • More

Your luxury holiday in Italy begins as soon as you reach the city of Bologna, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Journey into the unknown at Arco Del Meloncello, a unique attraction awaiting your visit. This remarkable arch has an average rating of 4.6 out of 5 stars from 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.

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

Make sure to reserve a table at Sfoglia Rina, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Va Mo Là, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria dal Biassanot, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Bar Freud E Squisito, a prime destination for a thrilling night out. Also, don’t forget to check out Osteria Del Sole, a bar that offers unique local touches. Likewise, Macondo - Cocktail Bar provides an excellent alternative for a fun evening.

Raise a toast to the start of your 9-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 218 km, 2 hours 57 min

  • Two Towers
  • International Museum and Library of Music
  • Piazza Santo Stefano
  • More

Wake up to day 2 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 Milan, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Bologna.

Make Two Towers your first stop of the day. Previous visitors have rated this tower an average of 4.7 out of 5 stars in 25,975 reviews.

Next up, make a stop at International Museum And Library Of Music. With an average rating of 4.5 out of 5 stars by 742 visitors, it's easy to understand why so many people visit this music museum every year. In fact, this attraction welcomes 13,413 annual visitors.

Piazza Santo Stefano is another attraction you can visit on this day of your vacation. This square has an average rating of 4.8 out of 5 stars by 7,617 visitors.

When you’re finished at Piazza Santo Stefano, the perfect next stop is Basilica Of San Domenico. This church is rated an average of 4.7 out of 5 stars in 3,380 reviews.

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.

Discover a world of culinary delights in Milan, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international, and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary, and modern cuisine in the city.

Cap off your dinner by heading to Nottingham Forest, ideal for a leisurely evening with a drink in hand. Armani/bamboo Bar is another bar that offers an enjoyable setting. Similarly, Mag Cafe is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 3

Day 3 – Milan

  • Milan
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Drive 8 km, 42 min

  • Piazza Gae Aulenti
  • Duomo di Milano
  • Royal Palace of Milan
  • Galleria Vittorio Emanuele II
  • La Scala
  • More

Day 3 of your luxury road trip in Italy begins and concludes in the city of Milan. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Milan, where you still have 1 night nights remaining.

An excellent attraction to start your day with is Piazza Gae Aulenti. This square is rated an average of 4.6 out of 5 stars in 30,398 reviews.

Continue your journey at Duomo Di Milano Museum. This art museum is rated 4.8 out of 5 stars by 138,554 travelers from near and far. Approximately 341,609 people come to this place of interest every year to enjoy a unique experience in Milan.

Milan is also the home of Royal Palace Of Milan. This art museum has an average rating of 4.6 out of 5 stars from 17,538 visitors.

You can continue your self-guided sightseeing tour at Galleria Vittorio Emanuele Ii. Rated 4.7 out of 5 stars by 91,394 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on La Scala. With an average rating of 4.7 out of 5 stars from 26,219 reviews, it’s hard to refuse the opportunity to see this opera house.

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 a delicious meal at Nero 9, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Ristorante la Brisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Milan this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Kilburn Cocktail Bar Milano, a well-loved spot among locals and tourists. Or, head to Bar Frida. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at The Friends Pub Milano, another top-rated place in the area.

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 4

Day 4 – Milan, and Genoa

  • Genoa
  • Milan
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Drive 150 km, 2 hours 44 min

  • Pinacoteca di Brera
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • Leonardo da Vinci Museum of Science and Technology
  • 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 Milan. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Pinacoteca Di Brera. This art museum is a popular stop on travelers’ itineraries in Milan, with an average rating of 4.7 out of 5 stars by 26,077 visitors. Around 417 people visit this attraction every year.

Sforzesco Castle Art Library is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 68,714 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Parco Sempione. Visitors have rated this park an average of 4.6 out of 5 stars in 72,914 reviews.

Arch Of Peace is another unique site you can experience today. This attraction is a monument rated an average of 4.6 out of 5 stars in 27,502 reviews.

Make your way to the fantastic Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", perhaps the most famous technology museum in Milan. This attraction welcomes around 532,084 visitors annually and is rated 4.5 out of 5 stars by 22,235 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.

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

Discover the culinary delights of Genoa by securing a reservation at The Cook. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of modern cuisine. For an alternative dining experience, try San Giorgio, renowned for its delicious modern, and ligurian dishes. This esteemed 1-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Marin, a highly recommended local eatery celebrated for its mouthwatering seafood, and contemporary menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

To truly maximize your evening out, consider visiting Scurreria Beer & Bagel after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to La Lepre, another bar with an inviting ambiance.

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

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Day 5

Day 5 – Genoa

  • Genoa
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Drive 2 km, 35 min

  • piazza De Ferrari
  • Genoa Cathedral
  • Aquarium of Genoa
  • porto antico
  • More

Day 5 of your luxury road trip in Italy begins and concludes in the city of Genoa. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Genoa, where you still have 1 night nights remaining.

Drop by the renowned Piazza De Ferrari. This popular square has been rated an average of 4.6 out of 5 stars by 34,312 visitors.

Another unforgettable place to experience is Genoa Cathedral. Rated 4.6 out of 5 stars by 8,971 visitors, this cathedral deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Aquarium Of Genoa. Hosting around 1,200,000 visitors every year, the fascinating Aquarium Of Genoa is one of the best places to visit in Genoa. This public aquarium has been rated an average of 4.5 out of 5 stars in 62,259 reviews.

Another favorite attraction in the area is Porto Antico. This port and popular place of interest enjoys a rating of 4.5 out of 5 stars from 12,414 local and international travelers.

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

Make sure to book a table at Vivarelli, a popular restaurant in Genoa. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Genoa at Trattoria Ugo, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is Tiflis Braceria Pizzeria. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Genoa tonight.

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 – Genoa, Pisa, and Florence

  • Florence
  • Pisa
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Drive 284 km, 3 hours 49 min

  • Leaning Tower of Pisa
  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Knights' Square
  • More

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa. The day's journey will conclude in Florence, a city that offers you comfort and relaxation for 2 nights. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

As you’ve unraveled the marvels of Genoa, 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 2 hours 6 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

An excellent attraction to start your day with is Leaning Tower Of Pisa. This bell tower typically receives around 3,200,000 visitors every year and is rated an average of 4.7 out of 5 stars in 116,882 reviews.

Continue your journey at Pisa Cathedral. This cathedral is rated 4.8 out of 5 stars by 8,361 travelers from near and far.

Pisa is also the home of Piazza Del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

You can continue your self-guided sightseeing tour at Knights' Square. Rated 4.5 out of 5 stars by 9,051 visitors, a visit to this top sight is time well spent.

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 full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Florence. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative, and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Il Palagio, a highly rated local gem known for its exquisite italian contemporary menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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 7

Day 7 – Florence

  • Florence
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Drive 7 km, 52 min

  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

Day 7 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.

Make Ponte Vecchio your first stop of the day. Previous visitors have rated this deck arch bridge an average of 4.7 out of 5 stars in 118,099 reviews.

Next up, make a stop at Uffizi Gallery. With an average rating of 4.7 out of 5 stars by 61,794 visitors, it's easy to understand why so many people visit this national museum every year. In fact, this attraction welcomes 2,011,219 annual visitors.

Piazza Della Signoria is another attraction you can visit on this day of your vacation. This square has an average rating of 4.8 out of 5 stars by 66,956 visitors.

When you’re finished at Piazza Della Signoria, the perfect next stop is Basilica Of Santa Croce In Florence. This church is rated an average of 4.7 out of 5 stars in 28,544 reviews.

If you’re keen to explore even more, then consider a visit to Piazzale Michelangelo. This square is a top place to visit, with a rating of 4.8 out of 5 stars from 77,744 reviews.

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.

Don’t miss out on dining at Trattoria Da Burde, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Ristorante Buca Mario, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Florence this evening.

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

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Day 8

Day 8 – Florence, and Bologna

  • Bologna
  • Florence
  • More

Drive 105 km, 1 hour 54 min

  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • Basilica of Santa Maria Novella
  • More

Wake up to day 8 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 Bologna, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

Take the opportunity to see Cathedral Of Santa Maria Del Fiore. This attraction has an average rating of 4.8 out of 5 stars from 76,359 visitors.

Galleria Dell'accademia is another sightseeing hotspot in the area. This national museum has been rated an average of 4.6 out of 5 stars by 34,429 travelers. Up to 1,719,645 people visit Galleria Dell'accademia every year.

Florence is also the home of Central Market. Around 43,100 people have rated this point of interest an average of 4.4 out of 5 stars.

Another place you’ll want to visit is Basilica Di Santa Maria Novella, Firenze (fi). With an average rating of 4.7 out of 5 stars from a total of 23,075 reviews, a visit to this archives is a great idea.

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.

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

Begin your culinary exploration in Bologna by securing a reservation at I Portici. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative, and contemporary cuisine. For another dining delight, visit Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Senza Nome, a well-loved spot among locals and tourists. Or, head to Bar Maurizio. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Brewdog Bar Bologna, another top-rated place in the area.

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

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Day 9

Day 9 – Bologna - departure day

  • Bologna - Departure day
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  • Piazza Maggiore
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Today is the last day of your 9-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 Piazza Maggiore. This extraordinary square and attraction is rated an average of 4.7 out of 5 stars in 64,523 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 delicious dinner at Trattoria del Tempo Buono, an excellent option for tonight's dining. Looking for something different? Cantina Bentivoglio offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante San Pietro.

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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