Luxury 6-Day Italy Road Trip from Bolzano to Trento, and Milan

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Escape for the holiday of a lifetime with this 6-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 2 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 6-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 6-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 6-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, Valeggio sul Mincio, Verona, Milan, and Monza 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. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

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

Enjoy a delicious meal at Stadt Hotel Città, a highly-rated dining destination in Bolzano. If you're eager to try something different, consider Alumix Cafè Ristorante Pizzeria, another top spot with a tantalizing menu. You might also want to secure a reservation at Castel Flavon. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Bolzano this evening.

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

Raise a toast to the start of your 6-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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On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bolzano, and Obereggen - San Floriano d'Ega. The day's journey will conclude in Trento, 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.

Journey into the unknown at South Tyrol Museum Of Archaeology, a unique attraction awaiting your visit. This remarkable archaeological museum has an average rating of 4.6 out of 5 stars from 9,935 reviews.

When you’re ready to continue your sightseeing, Museo Civico is a recommended place to visit. This museum is rated an average of 4.4 out of 5 stars in 126 reviews.

After soaking in Bolzano’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Obereggen - San Floriano d'Ega. Expect your car journey to take a minimum of 31 min. When you arrive in Obereggen - San Floriano d'Ega, it's time to take a break from the road.

Begin your sightseeing with a visit to Obereggen. This extraordinary 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 full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Trento. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Treat yourself to a delicious dinner at Ristorante Ca dei Gobj, an excellent option for tonight's dining. Looking for something different? il Circolino bar/ristorante offers a tantalizing alternative with its diverse menu. And don’t miss Urban Coffee Lab. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Trento.

Extend your evening after a delightful meal by visiting Tj Bar, which offers the perfect atmosphere for a night out. Moreover, Bar Pasi is another popular option for a drink or two. Likewise, Locanda Del Gatto Gordo also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 – Trento, Valeggio sul Mincio, Verona, and Milan

  • Milan
  • Valeggio sul Mincio
  • Verona
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Drive 286 km, 4 hours 30 min

  • Parco Giardino Sigurtà
  • Ponte Scaligero
  • Castelvecchio Museum
  • Verona Arena
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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 2 nights. The day's itinerary unfolds with a diverse array of experiences in Valeggio sul Mincio, and Verona.

Valeggio sul Mincio’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Trento behind. This drive usually takes around 1 hour 27 min. Valeggio sul Mincio welcomes you with a multitude of unique vacation experiences.

Start your sightseeing with a visit to Parco Giardino Sigurtà. This park is rated an average of 4.6 out of 5 stars from 27,387 visitors.

Continue your road trip and head to your next destination, Verona. This car ride takes around 48 min.

A top pick for your self-guided sightseeing tour today is Castelvecchio Bridge. Previous visitors have rated this arch bridge an average of 4.7 out of 5 stars in 12,156 reviews.

Castelvecchio Museum is a local recommendation that you also can pay a visit today. This art museum is rated an average of 4.6 out of 5 stars in 13,854 reviews. The attraction welcomes 35,031 visitors every year.

Another attraction you won't want to miss is Verona Arena. This opera house is rated an average of 4.7 out of 5 stars in 123,818 reviews. Every year, around 195,540 travelers visit this site to discover its unique features.

The attraction gets an estimated 35,031 visitors every year.

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 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 an outstanding dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an exceptional creative menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Seta by Antonio Guida, known for its delicious international, and contemporary cuisine. Another highly-recommended restaurant in Milan is Il Luogo Aimo e Nadia, a renowned restaurant with a 1-star Guide Michelin recognition, known for its delicious italian contemporary, and modern menu.

Continue the enjoyment post-dinner at Nottingham Forest, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Armani/bamboo Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Mag Cafe. 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 another amazing day of your luxury holiday in Valeggio sul Mincio, Italy and seize the opportunity to celebrate.

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Day 4

Day 4 – Milan

  • Milan
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Drive 5 km, 52 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Teatro alla Scala
  • Pinacoteca di Brera
  • Arco della Pace
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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 1 night nights remaining.

Seize the day by visiting some of the best attractions in the area, like Duomo Di Milano Museum. This extraordinary art museum has an average rating of 4.8 out of 5 stars from 138,554 visitors. Each year, around 341,609 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Galleria Vittorio Emanuele Ii. This commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

While in Milan, we also recommend a visit to La Scala. This opera house has been rated an average of 4.7 out of 5 stars in 26,219 reviews.

If you’re keen to explore even more, then consider a visit to Pinacoteca Di Brera. This attraction gets around 417 yearly visitors. With an average rating of 4.7 out of 5 stars by 26,077 travelers, this art museum is a highly recommended stop on your sightseeing around Milan.

Make your way to Arch Of Peace, perhaps the most famous monument in Milan. This attraction is rated an average of 4.6 out of 5 stars in 27,502 reviews.

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.

Savor the flavors at Nero 9, a top pick for dinner tonight. Alternatively, Ristorante la Brisa beckons with its unique menu offerings. Also, consider UNAHOTELS Cusani Milano. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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

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 – Milan, Monza, and Bolzano

  • Bolzano - Bozen
  • Milan
  • Monza
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Drive 303 km, 4 hours 22 min

  • Sforzesco Castle
  • Sempione Park
  • Piazza Gae Aulenti
  • Autodromo Nazionale Monza
  • Parco di Monza
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Wake up to day 5 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Milan, and Monza. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Take the opportunity to see Sforzesco Castle Art Library. This attraction has an average rating of 4.6 out of 5 stars from 68,714 visitors.

Parco Sempione is another sightseeing hotspot in the area. This park has been rated an average of 4.6 out of 5 stars by 72,914 travelers.

Milan is also the home of Piazza Gae Aulenti. Around 30,398 people have rated this square an average of 4.6 out of 5 stars.

Set your GPS to Monza and hit the road. Expect a journey of approximately 36 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Monza beckons with new experiences!

Start your sightseeing with a visit to Monza Circuit. This motorsport racing track is rated an average of 4.6 out of 5 stars from 14,877 visitors.

Monza Park is another popular attraction you could visit today. This park has a rating of 4.7 out of 5 stars from 34,629 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 day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Bolzano. Savor the local cuisine and relax as you recount the day's experiences.

Begin your culinary exploration in Bolzano by securing a reservation at In Viaggio - Claudio Melis. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative, and contemporary cuisine. For another dining delight, visit Vögele, celebrated for its delectable regional, and traditional menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday.

To truly maximize your evening out, consider visiting Tiffany Bolzano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Grifoncino, another bar with an inviting ambiance. Similarly, Bar Harley (franco L'eschimese) also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 – 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 6-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.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Bolzano'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 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 eager to try something different, consider Parkhotel Laurin, another top spot with a tantalizing 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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