Luxury 11-Day Italy Road Trip from Bologna to Milan, Pisa, Perugia, Rome, and Florence

Your luxury holiday in Italy begins as soon as you reach the city of Bologna, where you'll be staying for 1 night. 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 Bologna. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

Exploring the most popular attractions in Italy can make you lose track of time. Be sure to grab something to eat at one of the best restaurants in Bologna.

Treat yourself to an extraordinary dining experience at I Portici, one of the top Bib Gourmand restaurants in Bologna, holding 1 Michelin stars. Offering a diverse menu focusing on creative and contemporary cuisine, I Portici has earned praise from numerous satisfied guests.

A local favorite is Ahimè. Featuring country cooking cuisine, this popular luxury restaurant is a top choice for both locals and tourists.

As your day in Bologna is coming to an end, retreat to a bar where you can celebrate the adventures and experiences you've enjoyed so far on your exciting luxury holiday in Italy. Enjoy a signature cocktail or a glass of fine wine as you toast to more adventures that await you.

One of the top bars in Bologna is Va Mo Là. This claim is supported by 2,876 customers who have rated it an average of 4.3 out of 5 stars.

Another great bar with an extensive drink menu is Ca' Pelletti - Altabella. If you ask the 2,464 customers who have rated it an average of 4.3 out of 5 stars, Ca' Pelletti - Altabella is the perfect place for a unique drinking experience.

Locals also enjoy Cantina Bentivoglio, a great place to experience the local scene and unwind during your visit. This bar has an average rating of 4.4 out of 5 stars by 2,094 customers.

Raise a toast to the start of your 11-day luxury vacation in Italy and look forward to more fantastic days to come!

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 Bologna and Milan. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 2 nights at a luxury hotel in Milan adds a touch of comfort to your journey.

Make Fountain of Neptune, Bologna your first stop of the day. Previous visitors have rated this fountain an average of 4.7 out of 5 stars in 3,952 reviews.

Next up, make a stop at Palazzo Re Enzo. With an average rating of 4.6 out of 5 stars by 2,072 visitors, it's easy to understand why so many people visit this palazzo every year.

Piazza Maggiore is another attraction you can visit on this day of your vacation. This square has an average rating of 4.7 out of 5 stars by 64,523 visitors.

When you’re finished at Piazza Maggiore, the perfect next stop is Two Towers. This tower is rated an average of 4.7 out of 5 stars in 25,975 reviews.

If you’re keen to explore even more, then consider a visit to Piazza Santo Stefano. This square is a top place to visit, with a rating of 4.8 out of 5 stars from 7,617 reviews.

Continue your road trip and head to your next destination, Milan. This car ride takes around 2 hours 36 min.

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 Milan.

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.

One of the top restaurants in the area is Galleria Restaurant. This amazing restaurant offers great food meticulously prepared with the freshest ingredients. Over 2,024 diners have left the restaurant with an average rating of 4.4 out of 5 stars.

Another restaurant that many travelers recommend is Palazzo Parigi Hotel & Grand Spa Milano. Rated an average of 4.7 out of 5 stars by 1,550 customers, this restaurant is praised for its variety of dishes, warm ambiance, and amazing service.

You can also try the delicious food served at Vento di Sardegna for a unique dining experience. This restaurant has received approval from 1,063 tourists and locals alike, earning an average rating of 4.5 out of 5 stars in reviews.

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

When an after-dinner drink sounds enticing, visit Mag Cafe, one of the best bars in the city of Milan. This bar has an average rating of 4.4 out of 5 stars from 3,270 customers.

Get drinks as good as this day's adventure at Nottingham Forest. Considered one of the most popular bars in the city of Milan, this bar is rated an average of 4.4 out of 5 stars by 2,686 customers.

The Friends Pub Milano is also a great bar where you can have nice chats over delicious bites. The Friends Pub Milano has an average rating of 4.3 out of 5 stars from 1,689 customers.

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

On day 3 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Milan. You’ll stay in Milan for 1 night, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Milan to the fullest.

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

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

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Milan.

Many locals go to Kilburn Cocktail Bar Milano for an evening cocktail or glass of wine. This bar is rated an average of 4.5 out of 5 stars by 954 customers.

If you feel like going somewhere else, another popular option in the city is BhangraBar. This bar has an average rating of 4 out of 5 stars by 4,036 customers.

Camparino in Galleria is another great option in Milan, offering excellent drinks and a great atmosphere. This bar is rated an average of 4.4 out of 5 stars by 1,473 customers.

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

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan, Genoa, and Pisa. The day's journey will conclude in Pisa, 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.

When you're ready to see some sights, Cathedral Square is a great place to start with. This sightseeing destination is rated an average of 4.8 out of 5 stars by 7,539 visitors.

Another popular attraction you can visit today is Galleria Vittorio Emanuele II. This commercial gallery has an average rating of 4.7 out of 5 stars from 91,394 travelers.

We also recommend a stop at Duomo di Milano Museum. This site gets more than 341,609 visitors annually. The art museum has been rated an average of 4.8 out of 5 stars by 138,554 visitors.

When you’re ready to jump back into the car and say goodbye to Milan, you’ll hit the road in the direction of Genoa. This drive usually takes around 1 hour 58 min. When you arrive, enjoy some sightseeing.

An excellent attraction to start your day with is Spiaggia Pubblica di Priaruggia. This sightseeing destination is rated an average of 4.3 out of 5 stars in 2,161 reviews.

As you’ve unraveled the marvels of Genoa, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 2 hours 5 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Fasten your seatbelt and make your way to your next stop. Upon arrival, we highly recommend checking out some of the top attractions.

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

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.

At the top-rated restaurant Osteria I Santi, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.4 out of 5 stars by 3,094 customers.

If you feel like having something else, Filter Coffee Lab is another great option. This fantastic restaurant has an average rating of 4.6 out of 5 stars by 2,414 customers.

A third restaurant you could check out is Ristorante alle Bandierine. Ristorante alle Bandierine offers a menu of delicious dishes that are sure to satisfy your hunger. We’ll let its excellent rating of 4.5 out of 5 stars by 1,163 customers speak for itself.

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

If you’re up for classic drinks with a modern flair, consider going to Bar Mocambo. Around 359 customers have given this incredible bar an average rating of 4.7 out of 5 stars.

Locals of Pisa also enjoy the cocktails at Skyline American Bar. This place is rated an average of 4.3 out of 5 stars by 510 customers and is one of the best you can experience in the city.

Another top-rated alternative for an expertly crafted celebratory drink is Sud. This bar has an average rating of 4.6 out of 5 stars by 784 customers.

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 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 Perugia, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Pisa and Perugia.

Start your sightseeing with a visit to Knights' Square. This square is a popular stop on travelers’ itineraries in Pisa, with an average rating of 4.5 out of 5 stars by 9,051 visitors.

Leaning Tower of Pisa is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 116,882 reviews gives you an idea of other visitors’ experience at this attraction. It’s estimated that around 3,200,000 people visit this bell tower every year.

If it’s still bright and early, make your way to Pisa Cathedral. Visitors have rated this cathedral an average of 4.8 out of 5 stars in 8,361 reviews.

Piazza del Duomo, Pisa is another unique site you can experience today. This attraction is a square rated an average of 4.7 out of 5 stars in 104,550 reviews.

Make your way to the fantastic Campo santo, perhaps the most famous cemetery in Pisa. This attraction is rated 4.6 out of 5 stars by 586 travelers.

Fasten your seatbelt and make your way to your next stop. Perugia, 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 Pisa to Perugia may take around 2 hours 45 min without traffic disruptions. Upon arrival, we highly recommend checking out some of the top attractions.

When you arrive, enjoy some sightseeing.

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

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

Check out Ristorante Il Giurista. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.8 out of 5 stars from 980 reviews.

Locals also recommend Ristorante Al Tartufo as one of the best restaurants to have dinner at in Perugia. Ristorante Al Tartufo is rated an average of 4.7 out of 5 stars by 1,056 customers, including locals as well as travelers.

Alternatively, for another culinary experience you will remember, book a table at Osteria a Priori. This popular restaurant has an average rating of 4.5 out of 5 stars by 1,728 customers.

When you’ve finished your dinner at the best restaurant of your choice, and you’re in the mood for a drink, check out some of the best bars in the city.

Celebrate this wonderful day with sumptuous cocktails at Quei Bravi Ragazzi, a terrific bar to unwind after a busy day. Around 543 customers rated this bar with an impressive average of 4.7 out of 5 stars.

You can continue your amazing night of celebration at Elfo Pub Perugia. This bar has been rated an average of 4.6 out of 5 stars by 754 customers, and is an excellent place to mingle with locals and fellow travelers.

Transform your evening at Bar Pellas. This popular bar rated 4.3 out of 5 stars by 631 customers, offers great cocktails, good service, and a lovely atmosphere.

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

Wake up to day 6 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Vatican City and Rome. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 3 nights at a luxury hotel in Rome adds a touch of comfort to your journey.

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.

Fasten your seatbelt and make your way to your next stop. Upon arrival, we highly recommend checking out some of the top attractions.

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

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.

For a culinary experience you will remember, have a look at the menu at Tonnarello. With an average rating of 4.7 out of 5 stars by 62,881 customers, it’s truly one of the best restaurants in the whole of Rome.

If you feel like having something slightly different, check out Ristorante Pancrazio dal 1922. This is one of the most recommended restaurants in the city. Considering its average rating of 4.7 out of 5 stars by 2,946 customers, it’s one that most guests enjoy.

Cantina e Cucina is another restaurant you could book a table at tonight. This fantastic restaurant is often recommended by both travelers and locals in Rome, and has an impressive average rating of 4.6 out of 5 stars by 7,907 customers.

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

Whether you’d like to relax with a drink or you’re in the mood for some celebration, RoYaL Art Cafè Roma is a great place to end your evening at. Not sure whether this is a bar worth checking out? Then the average rating of 4.4 out of 5 stars from 3,972 in reviews might help make your mind up.

Alternatively, check out Ai Tre Scalini, a place many locals consider their favorite in Rome. Ai Tre Scalini offers plenty of drink options for every taste and is rated an average of 4.4 out of 5 stars by 3,972 guests.

If you want to continue your celebrations at another bar, try Centro. This bar is one of the best drinking spots in Rome and is rated an average of 4.4 out of 5 stars by 1,488 customers.

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 7 of your exciting luxury holiday across Italy, you will continue exploring the city of Rome. You still have 2 nights 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 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.

As your day in Rome is coming to an end, retreat to a bar where you can celebrate the adventures and experiences you've enjoyed so far on your exciting luxury holiday in Italy. Enjoy a signature cocktail or a glass of fine wine as you toast to more adventures that await you.

Whether you’d like to relax with a drink or you’re in the mood for some celebration, DEROMA - Farine Romane is a great place to end your evening at. Not sure whether this is a bar worth checking out? Then the average rating of 4.3 out of 5 stars from 1,432 in reviews might help make your mind up.

Alternatively, check out Hotel Hassler Roma, a place many locals consider their favorite in Rome. Hotel Hassler Roma offers plenty of drink options for every taste and is rated an average of 4.3 out of 5 stars by 1,432 guests.

If you want to continue your celebrations at another bar, try VinAllegro. This bar is one of the best drinking spots in Rome and is rated an average 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 8 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Rome. You’ll stay in Rome for 1 night, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Rome to the fullest.

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

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

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.

One of the top bars in Rome is Ristorante Tema. This claim is supported by 939 customers who have rated it an average of 4.4 out of 5 stars.

Another great bar with an extensive drink menu is La Botticella of Poggi Giovanni. If you ask the 655 customers who have rated it an average of 4.7 out of 5 stars, La Botticella of Poggi Giovanni is the perfect place for a unique drinking experience.

Locals also enjoy Sant' Eustachio Caffè, a great place to experience the local scene and unwind during your visit. This bar has an average rating of 4.2 out of 5 stars by 9,555 customers.

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.

On day 9 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.

Be one of the day’s first visitors at Trevi Fountain. This sculpture is rated an average of 4.8 out of 5 stars by 343,494 visitors.

When you’re finished at Trevi Fountain, head to Piazza di Spagna. This one-of-a-kind square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Spanish Steps. This monumental staircase is rated an average of 4.5 out of 5 stars by 57,211 visitors.

If you’re keen to explore more, then consider a visit to piazza del Popolo. This square is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 89,807 visitors.

To round off your sightseeing experience, make your way to Villa Borghese. This famous urban zone of rome is rated an average of 4.6 out of 5 stars by 69,749 travelers.

As you’ve unraveled the marvels of Rome, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Florence may take around 3 hours 4 min. Upon your arrival in Florence, you’ll be greeted with the opportunity to do some sightseeing and exploring.

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.

Locals enjoy eating at Ristorante Paoli, one of the most recommended restaurants in Florence. This city restaurant has an average rating of 4.9 out of 5 stars from 6,031 customers.

If you have an appetite for something else, check out Osteria Vecchio Cancello. Around 1,589 customers have given this fantastic restaurant an average of 4.8 out of 5 stars.

With an average rating of 4.7 out of 5 stars from 1,046 customers, Ristorante Oliviero 1962 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.

After an incredible dinner, cap off the night with a glass of beer, cocktail, or any refreshing drink.

Many locals go to Manifattura for an evening cocktail or glass of wine. This bar is rated an average of 4.7 out of 5 stars by 509 customers.

If you feel like going somewhere else, another popular option in the city is Caffe Concerto Paszkowski. This bar has an average rating of 4.3 out of 5 stars by 4,000 customers.

Ristorante Buca Mario is another great option in Florence, offering excellent drinks and a great atmosphere. This bar is rated an average of 4.4 out of 5 stars by 1,879 customers.

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 10 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 Florence and Bologna.

Take the opportunity to see piazza della Signoria. This attraction has an average rating of 4.8 out of 5 stars from 66,956 visitors.

Cathedral of Santa Maria del Fiore is another sightseeing hotspot in the area. This church has been rated an average of 4.8 out of 5 stars by 76,359 travelers.

Florence is also the home of Ponte Vecchio. Around 118,099 people have rated this deck arch bridge an average of 4.7 out of 5 stars.

Another place you’ll want to visit is Uffizi Gallery, which hosts up to 2,011,219 visitors every year. With an average rating of 4.7 out of 5 stars from a total of 61,794 reviews, a visit to this national museum is a great idea.

This day of your vacation in Florence is also your chance to admire piazzale Michelangelo. This must-visit square enjoys an average rating of 4.8 out of 5 stars from 77,744 reviews.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Bologna. Your travel time is around 1 hour 29 min.

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 Bologna.

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

At the top-rated restaurant Donatello, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.5 out of 5 stars by 2,700 customers.

If you feel like having something else, Trattoria dal Biassanot is another great option. This fantastic restaurant has an average rating of 4.4 out of 5 stars by 2,616 customers.

A third restaurant you could check out is Trattoria di Via Serra. Trattoria di Via Serra 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 1,547 customers speak for itself.

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 Bologna.

Cap off the evening at BrewDog Bar Bologna. This bar has an average rating of 4.5 out of 5 stars from 1,504 customers and is one of the best bars in Bologna.

Another popular place to go for refreshing drinks and delicious bites is Corner Bar. Rated an average of 4.5 out of 5 stars by 934 customers, this spot offers customers an unforgettable bar experience.

Macondo - Cocktail Bar is a great bar with a rating of 4.3 out of 5 stars from 808 customers. With this impressive average rating, Macondo - Cocktail Bar is certainly a great place to indulge in an exquisite glass of a cold, bubbly drink.

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

Today is the last day of your 11-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 Bologna before saying goodbye.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Bologna’s celebrated shopping district. Thanks to your stay’s premier location, you can easily visit the city’s commercial hubs and wander through its diverse range of local shops without rushing.

Whether you’re on a hunt for an ideal present to give to your friends or family, or looking for a personal memento to remind you of Italy, a variety of items are waiting for you.

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

One of the top restaurants in the area is Trattoria del Tempo Buono. This amazing restaurant offers great food meticulously prepared with the freshest ingredients. Over 1,531 diners have left the restaurant with an average rating of 4.6 out of 5 stars.

Another restaurant that many travelers recommend is Naama Cafè. Rated an average of 4.5 out of 5 stars by 1,538 customers, this restaurant is praised for its variety of dishes, warm ambiance, and amazing service.

You can also try the delicious food served at Ristorante da Nello al Montegrappa for a unique dining experience. This restaurant has received approval from 1,633 tourists and locals alike, earning an average rating of 4.4 out of 5 stars in reviews.

You will then say farewell to Bologna 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!