Luxury One-Week Italy Road Trip from Bologna traveling west to Milan, Genoa, and Florence

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Set off on the ultimate travel extravagance with this 8-day luxury road trip across Italy. Every aspect of your journey is crafted to provide a sophisticated and comfortable experience. Enjoy a holiday where luxury unfolds at every turn in each stop of your adventure in Italy.

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 3 nights in Bologna, 1 night in Milan, 1 night 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 8-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 8-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 8-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, Verona, Milan, Genoa, Pisa, Florence, and Siena 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 2 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

An excellent attraction to start your day with is Arco Del Meloncello. 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 full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Bologna. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Enjoy a delicious meal 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Freud E Squisito, known for its inviting atmosphere. Osteria Del Sole is another great option if you’re looking for a place to get the night started. Similarly, Macondo - Cocktail Bar provides a great setting to enjoy the night away.

Raise a toast to the start of your 8-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Bologna

  • Bologna
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Drive 1 km, 21 min

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

Day 2 of your luxury road trip in Italy begins and concludes in the city of Bologna. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Bologna, where you still have 1 night nights remaining.

Make Piazza Santo Stefano one of your first sightseeing stops in Bologna. Rated an average of 4.8 out of 5 stars by 7,617 travelers, a visit to this local attraction makes for a great introduction to the area.

Two Towers is a worthwhile attraction you can visit next. This tower is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 25,975 reviews.

Today is also the perfect opportunity to drop by Bologna Cathedral. This catholic cathedral has been rated an average of 4.6 out of 5 stars by 3,852 visitors.

If you’re keen to explore more, head to Piazza Maggiore. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 64,523 previous visitors.

Another top place to visit is Fountain Of Neptune, Bologna. This fountain enjoys an average rating of 4.7 out of 5 stars from 3,952 local and international travelers.

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

Enjoy an outstanding dining experience at I Portici, a 1-star Michelin restaurant offering an exceptional creative, and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby Bib Gourmand-awardee, Ahimè, known for its delicious country cooking cuisine. Another highly-recommended restaurant in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant, known for its delicious emilian menu.

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

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

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Day 3

Day 3 – Bologna, Verona, and Milan

  • Milan
  • Verona
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Drive 301 km, 4 hours 12 min

  • Castelvecchio Museum
  • Ponte Scaligero
  • Verona Arena
  • Piazza delle Erbe
  • More

Wake up to day 3 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Verona. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Verona. Your travel time is around 1 hour 47 min.

Begin your sightseeing with a visit to Castelvecchio Museum. This art museum gets 35,031 visitors each year and is rated an average of 4.6 out of 5 stars in 13,854 reviews.

Next up, make your way to Castelvecchio Bridge. This arch bridge has an average rating of 4.7 out of 5 stars from 12,156 reviews.

When you’re ready for your next sight of the day, continue to Verona Arena. This opera house has an average rating of 4.7 out of 5 stars from 123,818 visitors. Up to 195,540 people visit this place of interest annually.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza Delle Erbe. This square is rated an average of 4.7 out of 5 stars by 11,777 visitors.

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.

After exploring the unique sights of Italy, savor a delicious meal or get refreshed with a drink. We’ve gathered the most recommended restaurants and bars in the city of Milan for you so you can browse their menus in advance and make a reservation.

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.

If you’re not ready to end the night just yet, Nottingham Forest offers a perfect venue to relax and savor a drink. Similarly, Armani/bamboo Bar is well-suited for those looking to unwind in a social setting. Mag Cafe is another excellent spot to enjoy a nightcap after a delightful meal.

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 4

Day 4 – Milan, and Genoa

  • Genoa
  • Milan
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Drive 149 km, 2 hours 31 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Teatro alla Scala
  • Sforzesco Castle
  • Sempione Park
  • More

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan. The day's journey will conclude in Genoa, 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.

An excellent attraction to start your day with is Duomo Di Milano Museum. This art museum typically receives around 341,609 visitors every year and is rated an average of 4.8 out of 5 stars in 138,554 reviews.

Continue your journey at Galleria Vittorio Emanuele Ii. This commercial gallery is rated 4.7 out of 5 stars by 91,394 travelers from near and far.

Milan is also the home of La Scala. This opera house has an average rating of 4.7 out of 5 stars from 26,219 visitors.

You can continue your self-guided sightseeing tour at Sforzesco Castle Art Library. Rated 4.6 out of 5 stars by 68,714 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Parco Sempione. With an average rating of 4.6 out of 5 stars from 72,914 reviews, it’s hard to refuse the opportunity to see this park.

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.

Experience a harmony of flavors at The Cook in Genoa by securing a reservation in advance. Known for its 1-star Michelin status, The Cook offers a delightful variety of dishes highlighting its delicious modern menu. If you're seeking an alternative culinary experience, be sure to explore San Giorgio, a highly recommended restaurant known for its enticing modern, and ligurian cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Il Marin, a highly acclaimed restaurant celebrated for its exceptional seafood, and contemporary menu.

Explore the vibrant nightlife at Scurreria Beer & Bagel after your meal, a hub for lively evenings and memorable moments. Or, head to La Lepre for a great selection of flavorful drinks and a charming setting.

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

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Day 5

Day 5 – 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 5 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 Florence, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Genoa, and Pisa.

When you're ready to see some sights, Piazza De Ferrari is a great place to start. This square is rated an average of 4.6 out of 5 stars by 34,312 visitors.

Another popular attraction you can visit today is Aquarium Of Genoa. This public aquarium has an average rating of 4.5 out of 5 stars from 62,259 travelers. Every year, 1,200,000 travelers come to experience this site to make the most of their time in Genoa.

When you’ve had your share of Genoa, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 2 hours 3 min.

Take the opportunity to see Piazza Del Duomo, Pisa. This attraction has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Leaning Tower Of Pisa is another sightseeing hotspot in the area. This bell tower has been rated an average of 4.7 out of 5 stars by 116,882 travelers. Up to 3,200,000 people visit Leaning Tower Of Pisa every year.

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.

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

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative, and mediterranean cuisine. Another highly-recommended restaurant in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant with a 1-star Guide Michelin recognition, known for its delicious italian contemporary, and international menu.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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 6

Day 6 – 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 6 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.

Start your sightseeing with a visit to Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars from 118,099 visitors.

Uffizi Gallery is another popular attraction you could visit today. This national museum has a rating of 4.7 out of 5 stars from 61,794 visitors. Uffizi Gallery attracts up to 2,011,219 visitors every year.

Piazza Della Signoria is also highly recommended by travelers. This square has a rating of 4.8 out of 5 stars from 66,956 visitors.

Basilica Of Santa Croce In Florence is an attraction you won’t want to miss. This church is rated an average of 4.7 out of 5 stars in 28,544 reviews.

Another attraction you have the opportunity to visit today is Piazzale Michelangelo. This square has received an average rating of 4.8 out of 5 stars from 77,744 travelers.

After a long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Florence for you, so you can check out the menus and make your reservation in advance.

Have a fantastic dining experience at Trattoria Da Burde, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Buca Mario offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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 7

Day 7 – Florence, Siena, and Bologna

  • Bologna
  • Florence
  • Siena
  • More

Drive 249 km, 3 hours 48 min

  • Cathedral of Santa Maria del Fiore
  • Accademia Gallery
  • Piazza del Campo
  • More

Wake up to day 7 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Florence, and Siena. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Seize the day by visiting some of the best attractions in the area, like Cathedral Of Santa Maria Del Fiore. This extraordinary church has an average rating of 4.8 out of 5 stars from 76,359 visitors.

Next, make your way to Galleria Dell'accademia. This national museum welcomes around 1,719,645 visitors yearly and is rated an average of 4.6 out of 5 stars in 34,429 reviews.

While in Florence, we also recommend a visit to Central Market. This point of interest has been rated an average of 4.4 out of 5 stars in 43,100 reviews.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Siena. This drive usually takes around 1 hour 19 min, without any stops or traffic disruptions.

Make Piazza Del Campo your first stop of the day. Previous visitors have rated this square an average of 4.8 out of 5 stars in 64,175 reviews.

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.

After a day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Bologna. Savor the local cuisine and relax as you recount the day's experiences.

Make sure to reserve a table at Trattoria del Tempo Buono, 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 Cantina Bentivoglio, 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 Ristorante San Pietro, 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 Kinotto Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Mio Bar, a bar that offers unique local touches.

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 8

Day 8 – Bologna - departure day

  • Bologna - Departure day
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Today is the last day of your 8-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.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Bologna's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Villa Ghigi. This extraordinary park and attraction is rated an average of 4.7 out of 5 stars in 2,035 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.

If you're in the mood for something new, try Naama Cafè, another premier location with a delectable 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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