Luxury 14-Day Italy Road Trip from Milan traveling south to Pisa, Florence, Perugia, Rome, Arezzo, Venice, and Verona

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!

Make Piazza Gae Aulenti one of your first sightseeing stops in Milan. Rated an average of 4.6 out of 5 stars by 30,398 travelers, a visit to this local attraction makes for a great introduction to the area.

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.

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

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international, and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary, and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Nottingham Forest, a well-loved spot among locals and tourists. Or, head to Armani/Bamboo Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Mag Cafe, another top-rated place in the area.

Raise a toast to the start of your 14-day luxury vacation in Italy and look forward to more fantastic days to come!

Day 2 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.

Be one of the day’s first visitors at Duomo di Milano Museum. This art museum is rated an average of 4.8 out of 5 stars by 138,554 visitors. Attracting more than 341,609 yearly visitors, it’s a top sight you don’t want to miss.

When you’re finished at Duomo di Milano Museum, head to Galleria Vittorio Emanuele II. This one-of-a-kind commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Sforzesco Castle Art Library. This library is rated an average of 4.6 out of 5 stars by 68,714 visitors.

If you’re keen to explore more, then consider a visit to Parco Sempione. This park is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 72,914 visitors.

To round off your sightseeing experience, make your way to Arch of Peace. This famous monument is rated an average of 4.6 out of 5 stars by 27,502 travelers.

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.

As a top-rated it is an ideal choice in the city.

Keep the evening going at Kilburn Cocktail Bar Milano, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Frida, which offers a similarly pleasant setting and great drinks. Another option is The Friends Pub Milano, which provides an inviting environment for unwinding after a busy day out.

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

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 Milan, and Genoa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

When you’re ready for some sightseeing, make your way to Chiesa di Santa Maria presso San Satiro. This much-appreciated church is rated 4.7 out of 5 stars in 3,826 reviews.

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 56 min. When you arrive, enjoy some sightseeing.

Your sightseeing of the day begins at Piazza Fontane Marose, a remarkable point of interest where it’s easy to get lost in exploration. This top attraction is rated an average of 4.5 out of 5 stars in 446 reviews.

Next, satisfy your wanderlust at piazza De Ferrari. This square has an average rating of 4.6 out of 5 stars from 34,312 travelers.

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

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

Keep the excitement of the evening going by going to a bar or two. JEFFER cocktails & friends is an excellent place to start. You could also check out Le Parisien Wine Bar, offering a different kind of charm. A last recommendation for the day is Las Volta cocktailbar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 Florence, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Pisa.

When you're ready to see some sights, Leaning Tower of Pisa is a great place to start. This bell tower is rated an average of 4.7 out of 5 stars by 116,882 visitors. Leaning Tower of Pisa attracts more than 3,200,000 visitors every year.

Another popular attraction you can visit today is Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 travelers.

We also recommend a stop at Campo santo. The cemetery has been rated an average of 4.6 out of 5 stars by 586 visitors.

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

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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. Esteemed as a much-enjoyed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative, and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary, and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary, and international cuisine lovers seeking top-notch culinary experiences.

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, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

Day 5 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.

Make piazzale Michelangelo your first stop of the day. Previous visitors have rated this square an average of 4.8 out of 5 stars in 77,744 reviews.

Next up, make a stop at Uffizi Gallery. With an average rating of 4.7 out of 5 stars by 61,794 visitors, it's easy to understand why so many people visit this national museum every year. In fact, this attraction welcomes 2,011,219 annual visitors.

Ponte Vecchio is another attraction you can visit on this day of your vacation. This deck arch bridge has an average rating of 4.7 out of 5 stars by 118,099 visitors.

When you’re finished at Ponte Vecchio, the perfect next stop is piazza della Signoria. This square is rated an average of 4.8 out of 5 stars in 66,956 reviews.

If you’re keen to explore even more, then consider a visit to Basilica of Santa Croce in Florence. This church is a top place to visit, with a rating of 4.7 out of 5 stars from 28,544 reviews.

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

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.

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence. 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 Cathedral of Santa Maria del Fiore, a unique attraction awaiting your visit. This remarkable church has an average rating of 4.8 out of 5 stars from 76,359 reviews.

When you’re ready to continue your sightseeing, Basilica di Santa Maria Novella, Firenze (FI) is a recommended place to visit. This archives is rated an average of 4.7 out of 5 stars in 23,075 reviews.

Another must-see attraction in Florence is Central Market. Rated an average of 4.4 out of 5 stars by 43,100 travelers, this popular tourist destination in Florence offers an experience you will remember.

Galleria dell'Accademia is another popular stop on travelers' itineraries in Florence. This national museum promises memorable moments of exploring. Other travelers have rated this attraction 4.6 out of 5 stars in 34,429 reviews. Each year, approximately 1,719,645 people travel to visit Galleria dell'Accademia.

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

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

Following your dinner, dive into the local bar culture at Tommi Bar. Alternatively, go to Valentina, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffe Dal Perugino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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 Vatican City. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Fasten your seatbelt and make your way to your next stop. Vatican City, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Drop by the renowned Vatican Museums. This popular art museum has been rated an average of 4.6 out of 5 stars by 133,310 visitors. Based on recent data, this attraction is visited by more than 1,612,530 travelers every year.

Another unforgettable place to experience is Saint Peter's Square. Rated 4.8 out of 5 stars by 38,954 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Sistine Chapel. This chapel has been rated an average of 4.7 out of 5 stars in 52,083 reviews.

Another favorite attraction in the area is St. Peter's Basilica, drawing over 11,000,000 yearly visitors. This major basilica and popular place of interest enjoys a rating of 4.8 out of 5 stars from 131,043 local and international travelers.

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

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

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Known for its 3-star Michelin reputation, La Pergola captivates its guests with its exceptional variety of meals showcasing delicious mediterranean, and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative, and innovative dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean, and creative menu. With a 2-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Cap off your dinner by heading to La Botticella of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Sant' Eustachio Caffè is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

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.

Day 8 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 2 nights nights remaining.

Seize the day by visiting some of the best attractions in the area, like Trevi Fountain. This extraordinary sculpture has an average rating of 4.8 out of 5 stars from 343,494 visitors.

Next, make your way to Piazza di Spagna. This square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

While in Rome, we also recommend a visit to Spanish Steps. This monumental staircase has been rated an average of 4.5 out of 5 stars in 57,211 reviews.

If you’re keen to explore even more, then consider a visit to piazza del Popolo. With an average rating of 4.6 out of 5 stars by 89,807 travelers, this square is a highly recommended stop on your sightseeing around Rome.

Make your way to Villa Borghese, perhaps the most famous urban zone of rome in Rome. This attraction is rated an average of 4.6 out of 5 stars in 69,749 reviews.

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.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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

Day 9 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 1 night nights remaining.

Begin your sightseeing with a visit to Castel Sant'Angelo. This museum gets 918,591 visitors each year and is rated an average of 4.7 out of 5 stars in 72,431 reviews.

Next up, make your way to Piazza Navona. This square has an average rating of 4.7 out of 5 stars from 158,771 reviews.

When you’re ready for your next sight of the day, continue to Pantheon. This roman temple has an average rating of 4.8 out of 5 stars from 189,682 visitors. Up to 30,000,000 people visit this place of interest annually.

Beyond the above-mentioned attractions, you also have the opportunity to visit largo di Torre Argentina. This square is rated an average of 4.5 out of 5 stars by 30,433 visitors.

If you’re keen to explore even more, then consider a visit to Campo de' Fiori. This square is a much-appreciated attraction with an average rating of 4.4 out of 5 stars from 51,133 visitors.

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

Esteemed as a much-enjoyed restaurant, it features an exceptional menu.

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.

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

Drop by the renowned Capitoline Hill. This popular hill has been rated an average of 4.7 out of 5 stars by 19,557 visitors.

Another unforgettable place to experience is Roman Forum. Rated 4.7 out of 5 stars by 114,450 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Colosseum. Hosting around 7,400,000 visitors every year, the fascinating Colosseum is one of the best places to visit in Rome. This roman amphitheatre has been rated an average of 4.7 out of 5 stars in 328,821 reviews.

Another favorite attraction in the area is Circus Maximus. This circus and popular place of interest enjoys a rating of 4.4 out of 5 stars from 44,741 local and international travelers.

If you’re keen to explore even more, then consider a visit to Altare della Patria. This architectural structure gets around 1,683,070 annual visitors. With an average rating of 4.8 out of 5 stars from 49,843 travelers, this architectural structure is an attraction many avid travelers highly recommend visiting while in Rome.

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

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

Start your culinary exploration in Arezzo by securing a reservation at Octavin. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine.

Continue your evening by exploring the vibrant nightlife scene at Liquid Bar, a prime destination for a thrilling night out.

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 11 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna. 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 jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Bologna. This drive usually takes around 2 hours 5 min. When you arrive, enjoy some sightseeing.

Make Two Towers one of your first sightseeing stops in Bologna. Rated an average of 4.7 out of 5 stars by 25,975 travelers, a visit to this local attraction makes for a great introduction to the area.

Piazza Maggiore is a worthwhile attraction you can visit next. This square is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 64,523 reviews.

Today is also the perfect opportunity to drop by Bologna Cathedral. This catholic cathedral has been rated an average of 4.6 out of 5 stars by 3,852 visitors.

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

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

Experience a harmony of flavors at Local in Venice by securing a reservation in advance. Known for its 1-star Michelin status, Local offers a delightful variety of dishes highlighting its delicious contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Wistèria, a highly recommended restaurant known for its enticing contemporary, and venetian cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Quadri, a highly acclaimed restaurant celebrated for its exceptional modern menu.

Continue your lively evening at Al Parlamento, a perfect place for winding down or revving up the night, depending on which mood you’re in. Adagio is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Mercante 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.

Wake up to day 12 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Venice, and Padua. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Rialto Bridge. This stone bridge is rated an average of 4.7 out of 5 stars from 141,666 visitors.

Piazza San Marco is another popular attraction you could visit today. This square has a rating of 4.7 out of 5 stars from 152,982 visitors.

Doge's Palace is also highly recommended by travelers. More than 318,104 people visit this top attraction every year. This palace has a rating of 4.7 out of 5 stars from 24,775 visitors.

Continue your road trip and head to your next destination, Padua. This car ride takes around 39 min.

Journey into the unknown at The Basilica of St. Anthony, a unique attraction awaiting your visit. This remarkable church has an average rating of 4.8 out of 5 stars from 38,852 reviews.

When you’re ready to continue your sightseeing, prato della Valle is a recommended place to visit. This square is rated an average of 4.6 out of 5 stars in 47,576 reviews.

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

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

Experience a symphony of flavors at Casa Perbellini 12 Apostoli in Verona by securing a reservation in advance. Renowned for its 2-star Michelin distinction, Casa Perbellini 12 Apostoli 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 Il Desco, acclaimed for its delectable italian contemporary specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Osteria Mondo d'Oro, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for italian, and seasonal cuisine in the city.

To truly maximize your evening out, consider visiting Archivio after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to La Segreteria Café, another bar with an inviting ambiance. Similarly, Duchi Café also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Wake up to day 13 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 1 night. The day's itinerary unfolds with a diverse array of experiences in Verona, and Ronchi.

Begin your sightseeing with a visit to Verona Arena. This extraordinary opera house is rated an average of 4.7 out of 5 stars by 123,818 visitors. Each year, around 195,540 people visit this site to learn more about it.

Next, make your way to piazza delle Erbe. This top attraction is a square with an average rating of 4.7 out of 5 stars by 11,777 visitors.

Embrace the thrill of the open road as you wave goodbye to Verona and set your GPS to Ronchi. 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 36 min. Upon reaching Ronchi, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready to see some sights, Gardaland Resort is a great place to start. This amusement park is rated an average of 4.4 out of 5 stars by 99,291 visitors.

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.

Continue the enjoyment post-dinner at BhangraBar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Rufus Cocktail Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Ostello Bello Grande. 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 Verona, Italy and seize the opportunity to celebrate.

Today is the last day of your 14-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.

Maximize your last day in Italy and go on a shopping spree in Milan’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 Palazzo Borromeo. This extraordinary palazzo and attraction is rated an average of 4.3 out of 5 stars in 130 reviews, and is an excellent choice for your last sightseeing in Milan.

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

Treat yourself to a delicious dinner at Tommasi Milano, an excellent option for tonight's dining. Looking for something different? da Vic offers a tantalizing alternative with its diverse menu. And don’t miss G. B. Bar.

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!