Luxury One-Week Italy Road Trip from Milan traveling south to Bologna, Arezzo, Rome, and Florence

Your luxury holiday in Italy begins as soon as you reach the city of Milan. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

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

When you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

Elevate your stay in Milan by dining at this Bib Gourmand awarded restaurant. Renowned for its prestigious 3 Michelin-star rating and a variety of mouthwatering dishes, Enrico Bartolini al Mudec consistently impresses foreign and local diners, garnering praise for its exceptional creative cuisine.

Another popular dining spot in Milan is Seta by Antonio Guida, which holds a rating of 2 Michelin stars. This Bib Gourmand establishment’s inviting atmosphere and menu leave a lasting impression on everyone who dines here. Its international and contemporary menu, characterized by its exquisite flavors, is a true testament to Seta by Antonio Guida’s culinary excellence.

If you’re in the mood to try something different, consider reserving a table at Il Luogo Aimo e Nadia. This celebrated dining spot in Milan is renowned for its creative meals and italian contemporary and modern menu. Countless guests have praised this Bib Gourmand restaurant, adding to its 1 Michelin-star status.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

When you’ve finished your meal, visit Mag Cafe for a well-deserved after-dinner drink. One of the best bars in the city, Mag Cafe has an average rating of 4.4 out of 5 stars from 3,270 customers.

If you’d rather go to a different spot, Nottingham Forest is another great option. This bar enjoys an average rating of 4.4 out of 5 stars from 2,686 bar-goers.

The Friends Pub Milano is also a great city bar with a welcoming atmosphere. The Friends Pub Milano has an average rating of 4.3 out of 5 stars from 1,689 customers.

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

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan and Bologna. The day's journey will conclude in Bologna, 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.

Make Duomo di Milano Museum your first stop of the day. Previous visitors have rated this art museum an average of 4.8 out of 5 stars in 138,554 reviews. More than 341,609 people visit this place of interest every year.

Next up, make a stop at Galleria Vittorio Emanuele II. With an average rating of 4.7 out of 5 stars by 91,394 visitors, it's easy to understand why so many people visit this commercial gallery every year.

La Scala is another attraction you can visit on this day of your vacation. This opera house has an average rating of 4.7 out of 5 stars by 26,219 visitors.

When you’re finished at La Scala, the perfect next stop is Sforzesco Castle Art Library. This library is rated an average of 4.6 out of 5 stars in 68,714 reviews.

If you’re keen to explore even more, then consider a visit to Parco Sempione. This park is a top place to visit, with a rating of 4.6 out of 5 stars from 72,914 reviews.

Set your GPS to Bologna and hit the road. Expect a journey of approximately 2 hours 34 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bologna beckons with new experiences!

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

After a long day of exploring top attractions in the area, 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 the city for you, so you can check out the menus and make your reservation in advance.

Locals enjoy eating at Sfoglia Rina, one of the most recommended restaurants in Bologna. This city restaurant has an average rating of 4.5 out of 5 stars from 6,531 customers.

If you have an appetite for something else, check out Celtic Druid Irish Pub. Around 2,968 customers have given this fantastic restaurant an average of 4.5 out of 5 stars.

With an average rating of 4.5 out of 5 stars from 2,763 customers, Trattoria da Me is another excellent alternative that serves a whole menu of delectable dishes. Many patrons praise its unique ambiance and attentive service, making it a must-visit for both locals and tourists alike.

Bologna also has many fantastic bars that cater to all travel budgets.

If you’re up for classic drinks with a modern flair, consider going to Va Mo Là. Around 2,876 customers have given this incredible bar an average rating of 4.3 out of 5 stars.

Locals of Bologna also enjoy the cocktails at Ca' Pelletti - Altabella. This place is rated an average of 4.3 out of 5 stars by 2,464 customers and is one of the best you can experience in the city.

Another top-rated alternative for an expertly crafted celebratory drink is Cantina Bentivoglio. This bar has an average rating of 4.4 out of 5 stars by 2,094 customers.

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

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 Bologna, Arezzo, and Arezzo. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 1 night at a luxury hotel in Arezzo adds a touch of comfort to your journey.

Be one of the day’s first visitors at Fountain of Neptune, Bologna. This fountain is rated an average of 4.7 out of 5 stars by 3,952 visitors.

When you’re finished at Fountain of Neptune, Bologna, head to Piazza Maggiore. This one-of-a-kind square is rated an average of 4.7 out of 5 stars in 64,523 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Two Towers. This tower is rated an average of 4.7 out of 5 stars by 25,975 visitors.

If you’re keen to explore more, then consider a visit to Piazza Santo Stefano. This square is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 7,617 visitors.

Fasten your seatbelt and make your way to your next stop. Arezzo, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Bologna to Arezzo may take around 2 hours 17 min without traffic disruptions. Upon arrival, we highly recommend checking out some of the top attractions.

When you arrive, enjoy some sightseeing.

While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. The best things to do, see, and eat are waiting for you.

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

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

According to reviews, Il Covo dei Briganti is one of the absolute best places to eat in Arezzo. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.7 out of 5 stars from 509 reviews.

Alternatively, if you’re curious to try a local favorite, check out Trattoria Il Saraceno. This restaurant is rated an average of 4.3 out of 5 stars by 1,759 customers and guarantees you a nice dining experience to end your day.

If your taste buds call for something different, book a table at Antica Fonte. This popular restaurant has an average rating of 4.6 out of 5 stars by 1,306 customers.

Arezzo also has several great bars that will fit every travel budget.

Cap off the evening at La Clandestina. This bar has an average rating of 4.6 out of 5 stars from 277 customers and is one of the best bars in Arezzo.

Another popular place to go for refreshing drinks and delicious bites is Emilio. Rated an average of 4.6 out of 5 stars by 263 customers, this spot offers customers an unforgettable bar experience.

La Nuova Tagliatella is a great bar with a rating of 4.4 out of 5 stars from 275 customers. With this impressive average rating, La Nuova Tagliatella is certainly a great place to indulge in an exquisite glass of a cold, bubbly drink.

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.

Wake up to day 4 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 Rome, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City and Rome.

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

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

At the top-rated restaurant Tonnarello, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.7 out of 5 stars by 62,881 customers.

If you feel like having something else, Ristorante Pancrazio dal 1922 is another great option. This fantastic restaurant has an average rating of 4.7 out of 5 stars by 2,946 customers.

A third restaurant you could check out is Cantina e Cucina. Cantina e Cucina offers a menu of delicious dishes that are sure to satisfy your hunger. We'll let its excellent rating of 4.6 out of 5 stars by 7,907 customers speak for itself.

After dinner, visit some of the best bars in the city of Rome. Strike up a conversation with the friendly locals to end the day perfectly.

To have one of the best bar experiences in Rome, we recommend going to the wonderful RoYaL Art Cafè Roma. This bar offers a variety of phenomenal dishes and drinks and has been rated an average of 4.4 out of 5 stars by 3,972 customers.

If you would rather go somewhere else, check out Ai Tre Scalini. This is a favorite place to hang out among locals, and an excellent place to visit if you wish to make new acquaintances while enjoying a refreshing drink. Ai Tre Scalini has an average rating of 4.4 out of 5 stars from 2,950 customers.

Yet another excellent option is the popular Centro. This bar is rated an average of 4.4 out of 5 stars by 1,488 customers, so be sure to check out whether this is the place to celebrate tonight.

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.

On day 5 of your exciting luxury holiday across Italy, you will continue exploring the city of Rome. You still have 1 night left in the city. Enjoy your break from the road and spend this day sightseeing and eating at some of the best restaurants in Rome. Your accommodation will be conveniently located close to several of the best attractions in the city.

This activity is one of many you can add to your luxury travel plan to make your vacation in Italy truly memorable.

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

As your first day in Rome is coming to an end, retreat to a bar for some celebration. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

One of the top bars in Rome is DEROMA - Farine Romane. This claim is supported by 1,432 customers who have rated it an average of 4.3 out of 5 stars.

Another great bar with an extensive drink menu is Hotel Hassler Roma. If you ask the 895 customers who have rated it an average of 4.8 out of 5 stars, Hotel Hassler Roma is the perfect place for a unique drinking experience.

Locals also enjoy VinAllegro, a great place to experience the local scene and unwind during your visit. This bar has an average rating of 4.3 out of 5 stars by 1,167 customers.

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

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome and Florence. 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.

Make Roman Forum one of your first sightseeing stops in Rome. Rated an average of 4.7 out of 5 stars by 114,450 travelers, a visit to this local attraction makes for a great introduction to the area.

Colosseum is a worthwhile attraction you can visit next. This roman amphitheatre is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 328,821 reviews. Up to 7,400,000 travelers visit this site every year to make their time in Rome special.

Today is also the perfect opportunity to drop by Piazza Navona. This square has been rated an average of 4.7 out of 5 stars by 158,771 visitors.

If you’re keen to explore more, head to Altare della Patria and find out why 1,683,070 people visit this spot every year. A trip to this popular architectural structure is also your opportunity to see if it lives up to the reputable 4.8 out of 5-star rating as given by 49,843 previous visitors.

Another top place to visit is piazza del Popolo. This square enjoys an average rating of 4.6 out of 5 stars from 89,807 local and international travelers.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Florence. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 3 hours 1 min. Upon reaching Florence, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

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

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

At the top-rated restaurant Ristorante Paoli, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.9 out of 5 stars by 6,031 customers.

If you feel like having something else, Osteria Vecchio Cancello is another great option. This fantastic restaurant has an average rating of 4.8 out of 5 stars by 1,589 customers.

A third restaurant you could check out is Ristorante Oliviero 1962. Ristorante Oliviero 1962 offers a menu of delicious dishes that are sure to satisfy your hunger. We’ll let its excellent rating of 4.7 out of 5 stars by 1,046 customers speak for itself.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

Celebrate this wonderful day with sumptuous cocktails at Manifattura, a terrific bar to unwind after a busy day. Around 509 customers rated this bar with an impressive average of 4.7 out of 5 stars.

You can continue your amazing night of celebration at Caffe Concerto Paszkowski. This bar has been rated an average of 4.3 out of 5 stars by 4,000 customers, and is an excellent place to mingle with locals and fellow travelers.

Transform your evening at Ristorante Buca Mario. This popular bar rated 4.4 out of 5 stars by 1,879 customers, offers great cocktails, good service, and a lovely atmosphere.

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.

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, Parma, and Milan. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 1 night at a luxury hotel in Milan adds a touch of comfort to your journey.

Kick off the day at piazza della Signoria, a top pick for today’s sightseeing. This square is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Today is also your chance to visit Ponte Vecchio. Ponte Vecchio is a deck arch bridge with an average rating of 4.7 out of 5 stars from 118,099 reviews.

Cathedral of Santa Maria del Fiore is another top attraction we highly recommend you visit today. This church is rated an average of 4.8 out of 5 stars by 76,359 visitors.

Continue your road trip and head to your next destination, Parma. This car ride takes around 2 hours 13 min.

Make Palazzo della Pilotta one of your first sightseeing stops in Parma. Rated an average of 4.5 out of 5 stars by 5,085 travelers, a visit to this local attraction makes for a great introduction to the area. This palace attracts 60,666 visitors every year.

Milan’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Parma behind. This drive usually takes around 1 hour 34 min. Milan welcomes you with a multitude of unique vacation experiences.

Soak in the beautiful landscapes as you drive and look forward to exploring your next destination.

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

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 Milan. Savor the local cuisine and relax as you recount the day's experiences.

According to reviews, Primè is one of the absolute best places to eat in Milan. At this restaurant, you’ll enjoy a great atmosphere and a fantastic food and drinks menu. Primè is rated an average of 4.3 out of 5 stars by 1,184 customers.

Alternatively, if you’re curious to try a local favorite, check out Contraste. This restaurant is rated an average of 4.7 out of 5 stars by 823 customers and guarantees you a nice dining experience to end your day.

When your taste buds call for something different, you may want to pay Nero 9 a visit instead. This restaurant is a top recommendation often mentioned by both travelers and locals. Nero 9 has an average rating of 4.5 out of 5 stars by 573 customers.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Milan.

When you’ve finished your meal, visit Kilburn Cocktail Bar Milano for a well-deserved after-dinner drink. One of the best bars in the city, Kilburn Cocktail Bar Milano has an average rating of 4.5 out of 5 stars from 954 customers.

If you’d rather go to a different spot, BhangraBar is another great option. This bar enjoys an average rating of 4 out of 5 stars from 4,036 bar-goers.

Camparino in Galleria is also a great city bar with a welcoming atmosphere. Camparino in Galleria has an average rating of 4.4 out of 5 stars from 1,473 customers.

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

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 Milan before saying goodbye.

Make the most of your final day in Italy by visiting Milan’s iconic markets and shopping establishments. Your stay’s proximity to the city’s retail haven invites an unhurried and unforgettable exploration of its variety of stores and establishments.

Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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

One of the top restaurants in the area is Bice Restaurant. This amazing restaurant offers great food meticulously prepared with the freshest ingredients. Over 579 diners have left the restaurant with an average rating of 4.3 out of 5 stars.

Another restaurant that many travelers recommend is Ribot Restaurant. Rated an average of 4.5 out of 5 stars by 3,991 customers, this restaurant is praised for its variety of dishes, warm ambiance, and amazing service.

You can also try the delicious food served at L'immagine Bistrot Ristorante for a unique dining experience. This restaurant has received approval from 2,020 tourists and locals alike, earning an average rating of 4.7 out of 5 stars in reviews.

You will then say farewell to Milan 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!