Luxury 7-Day Italy Road Trip from Bolzano traveling south to Trento, and Milan

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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 Bolzano, 1 night in Trento, and 3 nights in Milan, 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 Bolzano, Trento, Monza, Milan, 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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Day 1

Day 1 – Bolzano - arrival day

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

A top pick for your self-guided sightseeing tour today is Waltherplatz. Previous visitors have rated this square an average of 4.5 out of 5 stars in 9,199 reviews.

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 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 Bolzano for you, so you can check out the menus and make your reservation in advance.

Savor the flavors at Stadt Hotel Città, a top pick for dinner tonight. Alternatively, Alumix Cafè Ristorante Pizzeria beckons with its unique menu offerings. Also, consider Castel Flavon. With its consistent customer satisfaction, it’s an excellent option for dining in Bolzano tonight.

Continue the enjoyment post-dinner at Café Gruber, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Franzbar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar La Nuova Grotta Del Corso. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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 – Bolzano, Obereggen - San Floriano d'Ega, and Trento

  • Trentino-Alto Adige/Südtirol
  • Bolzano - Bozen
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Drive 109 km, 1 hour 52 min

  • South Tyrol Archeological Museum
  • Museo Civico
  • Obereggen
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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, and Obereggen - San Floriano d'Ega. 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 South Tyrol Museum Of Archaeology. This extraordinary archaeological museum has an average rating of 4.6 out of 5 stars from 9,935 visitors.

Next, make your way to Museo Civico. This museum is rated an average of 4.4 out of 5 stars in 126 reviews.

Continue your road trip and head to your next destination, Obereggen - San Floriano d'Ega. This car ride takes around 31 min.

Be one of the day’s first visitors at Obereggen. This park is rated an average of 4.7 out of 5 stars by 3,863 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Trento. 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 Trento so you can check out the menus and make advance reservations.

Don’t miss out on dining at Ristorante Ca dei Gobj, a top-rated dining destination in Trento. If you're in the mood to try something new, consider il Circolino bar/ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Urban Coffee Lab. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Trento this evening.

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

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

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Day 3

Day 3 – Trento, Monza, and Milan

  • Milan
  • Trentino-Alto Adige/Südtirol
  • Monza
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Drive 253 km, 3 hours 40 min

  • Autodromo Nazionale Monza
  • Parco di Monza
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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 Milan, where you'll be staying for 3 nights. The day's itinerary unfolds with a diverse array of experiences in Trento, and Monza.

Be one of the day’s first visitors at Buonconsiglio Castle Museum. This museum is rated an average of 4.5 out of 5 stars by 11,838 visitors.

When you’re finished at Buonconsiglio Castle Museum, head to Muse. This one-of-a-kind museum is rated an average of 4.6 out of 5 stars in 20,032 reviews.

When you’ve had your share of Trento, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Monza. Your travel time is around 2 hours 30 min.

Make Monza Circuit one of your first sightseeing stops in Monza. Rated an average of 4.6 out of 5 stars by 14,877 travelers, a visit to this local attraction makes for a great introduction to the area.

Monza Park is a worthwhile attraction you can visit next. This park is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 34,629 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.

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 Milan for you, so you can check out the menus and make your reservation in advance.

Experience a harmony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Known for its 3-star Michelin status, Enrico Bartolini al Mudec offers a delightful variety of dishes highlighting its delicious creative menu. If you're seeking an alternative culinary experience, be sure to explore Seta by Antonio Guida, a highly recommended restaurant known for its enticing international, and contemporary cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Il Luogo Aimo e Nadia, a highly acclaimed restaurant celebrated for its exceptional italian contemporary, and modern menu.

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

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Day 4

Day 4 – Milan

  • Milan
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Drive 9 km, 45 min

  • Teatro alla Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Palazzo Reale di Milano
  • Piazza Gae Aulenti
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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 nights remaining.

When you’re ready for some sightseeing, make your way to La Scala. This much-appreciated opera house is rated 4.7 out of 5 stars in 26,219 reviews.

Next up is Galleria Vittorio Emanuele Ii. This commercial gallery has an average rating of 4.7 out of 5 stars from 91,394 visitors.

Another top sightseeing recommendation is Duomo Di Milano Museum. This art museum has been rated 4.8 out of 5 stars in 138,554 reviews. Every year, 341,609 travelers include this attraction on their travel itinerary.

Royal Palace Of Milan is another attraction you have the opportunity to visit today. This art museum has an average rating of 4.6 out of 5 stars from 17,538 reviews.

To continue your sightseeing, head over to Piazza Gae Aulenti. This square is rated an average of 4.6 out of 5 stars in 30,398 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 Milan so you can check out the menus and make advance reservations.

Treat yourself to a delightful dinner at Nero 9, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante la Brisa? It's another excellent option with a diverse menu. Consider reserving a table at UNAHOTELS Cusani Milano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

If you’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano is another excellent spot to enjoy a nightcap after a delightful meal.

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 11 km, 1 hour 3 min

  • Leonardo da Vinci Museum of Science and Technology
  • Pinacoteca di Brera
  • Sforzesco Castle
  • Sempione Park
  • Arco della Pace
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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 nights remaining.

Your sightseeing of the day begins at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a remarkable technology museum where it’s easy to get lost in exploration. This top attraction is rated an average of 4.5 out of 5 stars in 22,235 reviews. Each year, this popular place of interest welcomes approximately 532,084 visitors.

Next, satisfy your wanderlust at Pinacoteca Di Brera. This art museum has an average rating of 4.7 out of 5 stars from 26,077 travelers. Given the site's popularity, it’s easy to understand why more than 417 people visit it every year.

Sforzesco Castle Art Library is another must-visit attraction. This renowned library offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.6 out of 5 stars by 68,714 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 Parco Sempione. This well-loved park boasts a 4.6 out of 5-star rating from 72,914 reviews.

When there’s still energy left for exploring, Arch Of Peace awaits. If you’ve been interested in experiencing a monument, this is a top pick rated 4.6 out of 5 stars by 27,502 previous visitors.

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

Have a fantastic dining experience at Vento di Sardegna, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Palazzo Parigi Hotel & Grand Spa Milano offers an enticing alternative with its varied menu. Additionally, Galleria Restaurant is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Unwind after your meal by stepping into Bhangrabar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Rufus Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Ostello Bello Grande, another top-rated bar 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 6

Day 6 – Milan, Verona, and Bolzano

  • Bolzano - Bozen
  • Verona
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Drive 317 km, 4 hours 15 min

  • Piazza delle Erbe
  • Verona Arena
  • Castelvecchio Museum
  • Ponte Scaligero
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On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Verona. The day's journey will conclude in Bolzano, 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.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Verona. This drive usually takes around 2 hours 7 min, without any stops or traffic disruptions.

Begin your sightseeing with a visit to Piazza Delle Erbe. This square is rated an average of 4.7 out of 5 stars in 11,777 reviews.

Next up, make your way to Verona Arena. This opera house has an average rating of 4.7 out of 5 stars from 123,818 reviews. Usually, around 195,540 people visit Verona Arena every year.

When you’re ready for your next sight of the day, continue to Castelvecchio Museum. This art museum has an average rating of 4.6 out of 5 stars from 13,854 visitors. Up to 35,031 people visit this place of interest annually.

Beyond the above-mentioned attractions, you also have the opportunity to visit Castelvecchio Bridge. This arch bridge is rated an average of 4.7 out of 5 stars by 12,156 visitors.

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.

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

Enjoy an outstanding dining experience at In Viaggio - Claudio Melis, 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, Vögele, known for its delicious regional, and traditional cuisine.

If you’re not ready to end the night just yet, Tiffany Bolzano offers a perfect venue to relax and savor a drink. Similarly, Grifoncino is well-suited for those looking to unwind in a social setting. Bar Harley (franco L'eschimese) 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 stress-free luxury holiday in Italy has plenty more in store for you.

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Day 7

Day 7 – Bolzano - departure day

  • Bolzano - Bozen - Departure day
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  • Funivia del Colle
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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 Bolzano before saying goodbye.

Maximize your last day in Italy and go on a shopping spree in Bolzano’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Kohlerer Bahn. This extraordinary aerial 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 Parkhotel Laurin, 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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