Luxury One-Week Italy Self-Drive Road Trip With Itinerary from Bolzano traveling south to Venice, Milan, and Florence

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Experience travel that redefines comfort and elegance with this 8-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 Bolzano, 1 night in Venice, 3 nights in Milan, 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 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 Bolzano, Venice, Milan, Pisa, Florence, and Verona 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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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Waltherplatz
South Tyrol Archeological MuseumMuseo CivicoFondazione Museion
Rialto BridgePiazza San MarcoDoge's PalaceBridge of Sighs
Royal Palace of MilanCathedral SquareDuomo di MilanoGalleria Vittorio Emanuele IILa Scala
Leonardo da Vinci Museum of Science and TechnologyCastello SforzescoSempione ParkArch of PeacePiazza Gae AulentiDuomo di Milano
Pinacoteca di BreraPiazza del Duomo, PisaLeaning Tower of PisaDuomo di Milano
piazza della SignoriaPonte Vecchiopiazzale MichelangeloVerona Arena
Funivia del ColleSouth Tyrol Archeological Museum

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Day 1

Day 1 – Bolzano - arrival day

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

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

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

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 Bolzano for you so you can browse their menus in advance and make a reservation.

Have a fantastic dining experience at Anita, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Stadt Hotel Città offers an enticing alternative with its varied menu. Additionally, Danny is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bolzano.

Let the evening flow smoothly from dinner to drinks at Café Gruber, a top-rated bar in the area. For other recommendations, Franzbar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar La Nuova Grotta Del Corso offers a memorable night with diverse drink options and excellent service.

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 – Bolzano and Venice

  • Bolzano - Bozen
  • Venice
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Drive 269 km, 3 hours 5 min

  • South Tyrol Archeological Museum
  • Museo Civico
  • Fondazione Museion
  • More

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bolzano. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start by visiting South Tyrol Museum Of Archaeology, a prime spot to begin your journey. This eye-catching museum is sure to impress. Next on your list is Museo Civico, another must-visit landmark and often recommended museum renowned for its visually striking features.

While exploring and sightseeing, take time to savor the ambiance of Bolzano by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Museion. This photogenic museum is a remarkable attraction that offers a unique experience.

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

Experience a taste of local culinary excellence while in Venice by securing a table at Local. An esteemed 1-star Michelin restaurant, it features an exceptional contemporary menu. For an alternative taste experience, visit Wistèria, famous for its scrumptious contemporary and venetian dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Quadri, a local favorite celebrated for its exquisite modern cuisine in Venice. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for modern cuisine lovers seeking top-notch culinary experiences.

After your meal, keep the night alive at a bar like Al Parlamento, known for its lively atmosphere. The Caffe Rosso is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Adagio offers an excellent atmosphere for those looking to amp up the 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 – Venice and Milan

  • Venice
  • Milan
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Drive 265 km, 3 hours 12 min

  • Rialto Bridge
  • Piazza San Marco
  • Doge's Palace
  • Bridge of Sighs
  • More

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Venice. The day's journey will conclude in Milan, a city that offers you comfort and relaxation for 3 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Rialto Bridge. This globally renowned historical landmark provides an insightful glimpse into the city's identity. Next, discover Piazza San Marco, a culturally significant public square, promising a delightful encounter.

Continue your sightseeing with a visit to Doge's Palace, a captivating palace. When you’re done, don’t forget to make a stop at the popular Bridge Of Sighs.

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.

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.

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

  • Milan
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Drive 1 km, 20 min

  • Royal Palace of Milan
  • Cathedral Square
  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • La Scala
  • More

Day 4 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 2 nights remaining.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most well-known attractions included on the itinerary is Royal Palace Of Milan. This photogenic palace will help you start your sightseeing on top. Then, take a leisurely stroll to Cathedral Square and learn what makes this culturally significant public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the globally renowned Duomo Di Milano Museum. After exploring the church, head to Galleria Vittorio Emanuele Ii. This spectacular shopping mall is a highlight in Milan. Lastly, don’t forget to check out the well-known La Scala. Enjoy exploring this incredible opera house at your own pace.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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

Make sure to book a table at Dessert Bar Milano, a popular restaurant in Milan. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Milan at Radisson Blu Hotel Milan, 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 Ristorante Qui Si Mangia. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Milan tonight.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 5

Day 5 – Milan

  • Milan
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Drive 12 km, 1 hour 12 min

  • Leonardo da Vinci Museum of Science and Technology
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • Piazza Gae Aulenti
  • Duomo di Milano
  • More

Day 5 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 remaining.

Today’s route brings an instagrammable, a history-steeped, a stunning, a symbolic, a charming, a beautiful, and a detailed. The first attraction of today is Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This popular museum is a heritage-rich place to see in Milan. Continue your discovery at Sforzesco Castle Art Library, a culturally significant castle with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Parco Sempione. This top-rated park offers a romantic encounter with Milan. Arch Of Peace is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Milan.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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 Milan so you can check out the menus and make advance reservations.

Enjoy a delicious meal at Bice Restaurant, a highly-rated dining destination in Milan. If you're eager to try something different, consider Alto Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

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

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 6

Day 6 – Milan, Pisa, and Florence

  • Milan
  • Pisa
  • Florence
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Drive 379 km, 5 hours 1 min

  • Pinacoteca di Brera
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Duomo di Milano
  • More

Wake up to day 6 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 1 night. The day's itinerary unfolds with a diverse array of experiences in Milan and Pisa.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Milan behind. This drive usually takes around 3 hours 13 min. Pisa welcomes you with a multitude of unique vacation experiences.

Begin your journey at Piazza Del Duomo, Pisa and explore the stunning features. Next, make your way to Leaning Tower Of Pisa, another highlight in the city.

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

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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 7

Day 7 – Florence, Verona, and Bolzano

  • Florence
  • Verona
  • Bolzano - Bozen
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Drive 393 km, 5 hours 7 min

  • piazza della Signoria
  • Ponte Vecchio
  • piazzale Michelangelo
  • Verona Arena
  • 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 Verona. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Today’s route brings a charming, a mesmerizing, an instagrammable, a respected, a symbolic, and a remarkable. The first attraction of today is Piazza Della Signoria. This widely recognized public square is an enchanting place to see in Florence. Continue your discovery at Ponte Vecchio, a visually striking historical landmark with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazzale Michelangelo. This spectacular observation deck offers a culturally significant encounter with Florence.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Verona. This drive usually takes around 2 hours 43 min. When you arrive, enjoy some sightseeing.

Take your self-guided tour to Verona Arena, a wondrous stadium that everyone visiting Verona should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings.

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

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

Experience a symphony of flavors at In Viaggio - Claudio Melis in Bolzano by securing a reservation in advance. Renowned for its 1-star Michelin distinction, In Viaggio - Claudio Melis delights its guests with its exceptional variety of meals showcasing delicious creative and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Vögele, acclaimed for its delectable regional and traditional specialties. This local Bib Gourmand establishment consistently satisfies guests, ensuring an unforgettable holiday experience.

Following your dinner, dive into the local bar culture at Tiffany Bolzano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Corte - Bar & Bistro, the perfect place for those looking to experience the best of the nightlife. Similarly, Hollywood provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 8

Day 8 – Bolzano - departure day

  • Bolzano - Bozen - Departure day
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  • Funivia del Colle
  • South Tyrol Archeological Museum
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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 Bolzano before saying goodbye.

Make the most of your final day in Italy by visiting Bolzano’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 Kohlerer Bahn. This extraordinary tramway and attraction is rated an average of 4.4 out of 5 stars in 767 reviews, and is an excellent choice for your last sightseeing in Bolzano.

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

If you're in the mood to try something new, consider Black Sheep Drink Differently, another top spot with a mouthwatering menu.

You will then say farewell to Bolzano 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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