Luxury 7-Day Italy Road Trip from Florence traveling west to Pisa, Milan, Verona, and Bologna

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Escape for the holiday of a lifetime with this 7-day luxury road trip 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 2 nights in Florence, 1 night in Pisa, 1 night in Milan, 1 night in Verona, and 1 night in Bologna, 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 7-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 7-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 7-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 Florence, Pisa, Genoa, Milan, Verona, Valeggio sul Mincio, Bologna, 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 – Florence - arrival day

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

Make Central Market your first stop of the day. Previous visitors have rated this sightseeing destination an average of 4.4 out of 5 stars in 43,100 reviews.

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

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.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Caffe San Firenze, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ditta Artigianale. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Florence this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to the start of your 7-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Florence, and Pisa

  • Pisa
  • Florence
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Drive 83 km, 1 hour 33 min

  • Piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • Piazza della Repubblica
  • 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 Pisa, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

Your sightseeing of the day begins at Piazza Della Signoria, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Next, satisfy your wanderlust at Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars from 61,794 travelers. Given the site's popularity, it’s easy to understand why more than 2,011,219 people visit it every year.

Ponte Vecchio is another must-visit attraction. This renowned deck arch bridge offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 118,099 travelers, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Cathedral Of Santa Maria Del Fiore. This well-loved church boasts a 4.8 out of 5-star rating from 76,359 reviews.

When there’s still energy left for exploring, Piazza Della Repubblica awaits. If you’ve been interested in experiencing a square, this is a top pick rated 4.6 out of 5 stars by 22,356 previous visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Pisa. 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 Pisa.

Treat yourself to a wonderful meal at Ristorante Capodimonte Pisa, a top-rated dining spot in Pisa. If you're in the mood for something new, try Baribaldi Pisa, another premier location with a delectable menu. You might also want to book a table at Restaurant -Pizzeria Il Mio Capriccio. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

Unwind after your meal by stepping into Jeffer Cocktails & Friends. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Le Parisien Wine Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Las Volta Cocktailbar, another top-rated bar in the area.

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

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Day 3

Day 3 – Pisa, Genoa, and Milan

  • Milan
  • Pisa
  • Genoa
  • More

Drive 302 km, 3 hours 59 min

  • Leaning Tower of Pisa
  • Piazza del Duomo
  • Cattedrale di Pisa
  • More

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa, and Genoa. 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.

Take the opportunity to see Leaning Tower Of Pisa. This attraction has an average rating of 4.7 out of 5 stars from 116,882 visitors and gets around 3,200,000 visits every year.

Piazza Del Duomo, Pisa is another sightseeing hotspot in the area. This square has been rated an average of 4.7 out of 5 stars by 104,550 travelers.

Pisa is also the home of Pisa Cathedral. Around 8,361 people have rated this cathedral an average of 4.8 out of 5 stars.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Genoa. Expect your car journey to take a minimum of 1 hour 43 min. When you arrive in Genoa, it's time to take a break from the road.

Be one of the day’s first visitors at Spiaggia Pubblica Di Priaruggia. This point of interest is rated an average of 4.3 out of 5 stars by 2,161 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 a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Milan. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international, and contemporary dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary, and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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.

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

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Day 4

Day 4 – Milan, and Verona

  • Verona
  • Milan
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Drive 167 km, 2 hours 31 min

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

Begin your sightseeing with a visit to Duomo Di Milano Museum. This extraordinary art museum is rated an average of 4.8 out of 5 stars by 138,554 visitors. Each year, around 341,609 people visit this site to learn more about it.

Next, make your way to Galleria Vittorio Emanuele Ii. This top attraction is a commercial gallery with an average rating of 4.7 out of 5 stars by 91,394 visitors.

We also recommend a visit to Sforzesco Castle Art Library. This library is rated 4.6 out of 5 stars by 68,714 travelers.

If you’re keen to keep exploring, visit Parco Sempione. This highly recommended sightseeing destination has received an average rating of 4.6 out of 5 stars from 72,914 travelers.

Today is also your chance to spend some time at Piazza Gae Aulenti. This square is rated an average of 4.6 out of 5 stars by 30,398 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Verona. 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 Verona. Savor the local cuisine and relax as you recount the day's experiences.

Prepare for an extraordinary culinary adventure in Verona by booking a table at Casa Perbellini 12 Apostoli, a 2-star Michelin restaurant that boasts an exceptional creative, and contemporary menu. For a different flavor experience, head to Il Desco, renowned for its delectable italian contemporary dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Osteria Mondo d'Oro, a local gem known for its delightful italian, and seasonal cuisine in Verona. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

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

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 5

Day 5 – Verona, Ronchi, Valeggio sul Mincio, and Bologna

  • Bologna
  • Verona
  • Valeggio sul Mincio
  • More

Drive 182 km, 3 hours

  • Verona Arena
  • Gardaland Resort
  • Parco Giardino Sigurtà
  • 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 Bologna, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Verona, Ronchi, and Valeggio sul Mincio.

When you're ready to see some sights, Verona Arena is a great place to start. This opera house is rated an average of 4.7 out of 5 stars by 123,818 visitors. Verona Arena attracts more than 195,540 visitors every year.

Continue your road trip and head to your next destination, Ronchi. This car ride takes around 35 min.

Your sightseeing of the day begins at Gardaland Resort, a remarkable amusement park where it’s easy to get lost in exploration. This top attraction is rated an average of 4.4 out of 5 stars in 99,291 reviews.

When you’re ready to jump back into the car and say goodbye to Ronchi, you’ll hit the road in the direction of Valeggio sul Mincio. This drive usually takes around 29 min. When you arrive, enjoy some sightseeing.

Take the opportunity to see Parco Giardino Sigurtà. This attraction has an average rating of 4.6 out of 5 stars from 27,387 visitors.

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.

Have a memorable dining experience in Bologna by booking a table at I Portici, renowned as a 1-star Michelin restaurant presenting an exceptional creative, and contemporary menu. For a different culinary experience in Bologna, Ahimè shines as one of the top destinations, known for its delicious country cooking cuisine. This Bib Gourmand-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Trattoria di Via Serra is known as a top local spot for its delicious emilian cuisine in Bologna. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

Explore the vibrant nightlife at Bar Freud E Squisito after your meal, a hub for lively evenings and memorable moments. Or, head to Osteria Del Sole for a great selection of flavorful drinks and a charming setting. Furthermore, Macondo - Cocktail Bar is perfect for those looking to extend their night with a touch of local flavor.

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 – Bologna, Siena, and Florence

  • Florence
  • Bologna
  • Siena
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Drive 248 km, 3 hours 40 min

  • Two Towers
  • Piazza Maggiore
  • Piazza del Campo
  • Duomo di Siena
  • More

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna, and Siena. The day's journey will conclude in Florence, 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.

A top pick for your self-guided sightseeing tour today is Two Towers. Previous visitors have rated this tower an average of 4.7 out of 5 stars in 25,975 reviews.

Piazza Maggiore is a local recommendation that you also can pay a visit today. This square is rated an average of 4.7 out of 5 stars in 64,523 reviews.

Set your GPS to Siena and hit the road. Expect a journey of approximately 2 hours 11 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

Start your sightseeing with a visit to Piazza Del Campo. This square is rated an average of 4.8 out of 5 stars from 64,175 visitors.

Siena Cathedral is another popular attraction you could visit today. This domus has a rating of 4.8 out of 5 stars from 21,656 visitors.

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.

Discover a world of culinary delights in Florence, 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.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative, and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary, and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

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 - departure day

  • Florence - Departure day
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  • Piazzale Michelangelo
  • More

Today is the last day of your 7-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 Florence before saying goodbye.

Make the most of your final day in Italy by visiting Florence’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Piazzale Michelangelo. This extraordinary square and attraction is rated an average of 4.8 out of 5 stars in 77,744 reviews, and is an excellent choice for your last sightseeing in Florence.

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

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu.

You will then say farewell to Florence 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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