Luxury Two-Week Italy Road Trip from Perugia to Rome, Florence, Bologna, Milan, and Pisa

Your luxury holiday in Italy begins as soon as you reach the city of Perugia, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Be one of the day’s first visitors at Etruscan Arch. This architectural element is rated an average of 4.7 out of 5 stars by 1,190 visitors.

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

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

This renowned restaurant holds , and offers an exceptional menu of cuisine.

Extend your evening after a delightful meal by visiting Tommi Bar, which offers the perfect atmosphere for a night out. Moreover, Valentina is another popular option for a drink or two. Likewise, Caffe Dal Perugino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise a toast to the start of your 15-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 Magione and Perugia. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Take the opportunity to see Parco Regionale del Lago Trasimeno. This attraction has an average rating of 4.4 out of 5 stars from 8,831 visitors.

Set your GPS to Perugia and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Perugia beckons with new experiences!

Seize the day by visiting some of the best attractions in the area, like Carducci Gardens. This extraordinary park has an average rating of 4.5 out of 5 stars from 1,768 visitors.

Next, make your way to Porta Marzia. This city gate is rated an average of 4.6 out of 5 stars in 119 reviews.

While in Perugia, we also recommend a visit to Rocca Paolina. This rocca has been rated an average of 4.7 out of 5 stars in 7,128 reviews.

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.

Have a memorable dining experience in Rome by booking a table at La Pergola, renowned as a 3-star Michelin restaurant presenting an exceptional mediterranean and contemporary menu. For a different culinary experience, Il Pagliaccio shines as one of the top destinations known for its delicious creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Enoteca La Torre is known as a top local spot for its delicious mediterranean and creative cuisine in Rome. This 2-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Explore the vibrant nightlife at La Botticella of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Sant' Eustachio Caffè for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

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.

Day 3 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 4 nights nights remaining.

Your sightseeing of the day begins at Castel Sant'Angelo, a remarkable museum where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 72,431 reviews. Each year, this popular place of interest welcomes approximately 918,591 visitors.

Next, satisfy your wanderlust at Basilica di Santa Maria Maggiore. This major basilica has an average rating of 4.8 out of 5 stars from 27,678 travelers.

Altare della Patria is another must-visit attraction. This renowned architectural structure offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 49,843 travelers and attracting 1,683,070 annual visitors, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit largo di Torre Argentina. This well-loved square boasts a 4.5 out of 5-star rating from 30,433 reviews.

When there’s still energy left for exploring, Campo de' Fiori awaits. If you’ve been interested in experiencing a square, this is a top pick rated 4.4 out of 5 stars by 51,133 previous visitors.

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

To truly maximize your evening out, consider visiting The Apartment Bar Roma after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Hotel Hassler Roma, another bar with an inviting ambiance.

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 4 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 3 nights nights remaining.

A top pick for your self-guided sightseeing tour today is Villa Borghese. Previous visitors have rated this urban zone of rome an average of 4.6 out of 5 stars in 69,749 reviews.

Piazza del Popolo is a local recommendation that you also can pay a visit today. This square is rated an average of 4.6 out of 5 stars in 89,807 reviews.

Another attraction you won't want to miss is Roman Forum. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Colosseum is another outstanding experience in Rome. Around 328,821 travelers have rated this roman amphitheatre an average of 4.7 out of 5 stars. The attraction hosts 7,400,000 visitors annually.

If you long for more, Circus Maximus is not far away. This circus is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.4 out of 5 stars in 44,741 reviews.

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

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

Day 5 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.

An excellent attraction to start your day with is Piazza Navona. This square is rated an average of 4.7 out of 5 stars in 158,771 reviews.

Continue your journey at Pantheon. This roman temple is rated 4.8 out of 5 stars by 189,682 travelers from near and far. Approximately 30,000,000 people come to this place of interest every year to enjoy a unique experience in Rome.

Rome is also the home of Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars from 343,494 visitors.

You can continue your self-guided sightseeing tour at Piazza di Spagna. Rated 4.7 out of 5 stars by 113,658 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Spanish Steps. With an average rating of 4.5 out of 5 stars from 57,211 reviews, it’s hard to refuse the opportunity to see this monumental staircase.

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.

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

Day 6 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.

Discover a world of culinary delights in Rome, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

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 7 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 Arezzo.

Set your GPS to Arezzo and hit the road. Expect a journey of approximately 2 hours 37 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Arezzo beckons with new experiences!

Begin your sightseeing with a visit to Lignano Park - Rigutinelli. This park is rated an average of 4.5 out of 5 stars in 754 reviews.

Next up, make your way to San Francesco, Arezzo. This minor basilica has an average rating of 4.6 out of 5 stars from 2,377 reviews. Usually, around 20,939 people visit San Francesco, Arezzo every year.

When you’re ready for your next sight of the day, continue to Santa Maria della Pieve. This church building has an average rating of 4.8 out of 5 stars from 720 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit piazza Grande. This square is rated an average of 4.6 out of 5 stars by 14,465 visitors.

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

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

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated it is an ideal choice for italian contemporary and international cuisine in the city.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, SE·STO on Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

Day 8 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.

Drop by the renowned piazzale Michelangelo. This popular square has been rated an average of 4.8 out of 5 stars by 77,744 visitors.

Another unforgettable place to experience is Uffizi Gallery. Rated 4.7 out of 5 stars by 61,794 visitors, this national museum deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Ponte Vecchio. This deck arch bridge has been rated an average of 4.7 out of 5 stars in 118,099 reviews.

Another favorite attraction in the area is piazza della Signoria. This square and popular place of interest enjoys a rating of 4.8 out of 5 stars from 66,956 local and international travelers.

If you’re keen to explore even more, then consider a visit to Basilica of Santa Croce in Florence. With an average rating of 4.7 out of 5 stars from 28,544 travelers, this church is an attraction many avid travelers highly recommend visiting while 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.

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 9 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.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Bologna. This drive usually takes around 1 hour 24 min, without any stops or traffic disruptions.

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, Galleria dell'Accademia is a recommended place to visit. This national museum is rated an average of 4.6 out of 5 stars in 34,429 reviews. Based on recent data, the attraction hosts 1,719,645 visitors per year.

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.

Basilica di Santa Maria Novella, Firenze (FI) is another popular stop on travelers' itineraries in Florence. This archives promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 23,075 reviews.

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

Discover a world of culinary delights in Bologna, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Enjoy an outstanding dining experience at I Portici, a 1-star Michelin restaurant offering an exceptional creative and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby Bib Gourmand-awardee, Ahimè, known for its delicious country cooking cuisine. Another highly-recommended restaurant in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant , known for its delicious emilian menu.

After savoring a delicious meal, step into the vibrant nightlife at Bar Freud e Squisito, where the evening is just getting started. In the same way, Osteria del Sole offers a unique charm perfect for experiencing the local bar scene in Bologna. Macondo - Cocktail Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Embrace the thrill of the open road as you wave goodbye to Bologna and set your GPS to Milan. 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 2 hours 26 min. Upon reaching Milan, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Start your sightseeing with a visit to Bologna Cathedral. This catholic cathedral is a popular stop on travelers’ itineraries in Bologna, with an average rating of 4.6 out of 5 stars by 3,852 visitors.

Piazza Santo Stefano is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 7,617 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Two Towers. Visitors have rated this tower an average of 4.7 out of 5 stars in 25,975 reviews.

Piazza Maggiore is another unique site you can experience today. This attraction is a square rated an average of 4.7 out of 5 stars in 64,523 reviews.

Make your way to the fantastic Fountain of Neptune, Bologna, perhaps the most famous fountain in Bologna. This attraction is rated 4.7 out of 5 stars by 3,952 travelers.

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.

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its , this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international and contemporary dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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.

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.

Day 11 of your luxury road trip in Italy begins and concludes in the city of Milan. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Milan, where you still have 2 nights nights remaining.

Take the opportunity to see Royal Palace of Milan. This attraction has an average rating of 4.6 out of 5 stars from 17,538 visitors.

Duomo di Milano Museum is another sightseeing hotspot in the area. This art museum has been rated an average of 4.8 out of 5 stars by 138,554 travelers. Up to 341,609 people visit Duomo di Milano Museum every year.

Milan is also the home of Galleria Vittorio Emanuele II. Around 91,394 people have rated this commercial gallery an average of 4.7 out of 5 stars.

Another place you’ll want to visit is La Scala. With an average rating of 4.7 out of 5 stars from a total of 26,219 reviews, a visit to this opera house is a great idea.

This day of your vacation in Milan is also your chance to admire Piazza Gae Aulenti. This must-visit square enjoys an average rating of 4.6 out of 5 stars from 30,398 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 Milan.

Cap off your dinner by heading to Kilburn Cocktail Bar Milano, ideal for a leisurely evening with a drink in hand. Bar Frida is another bar that offers an enjoyable setting. Similarly, The Friends Pub Milano 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 12 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.

Start your sightseeing with a visit to Basilica di Sant'Ambrogio. This church is a popular stop on travelers’ itineraries in Milan, with an average rating of 4.7 out of 5 stars by 12,883 visitors.

Santa Maria delle Grazie Church is another popular place of interest you can visit today. The average rating of 4.5 out of 5 stars from 13,490 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Sforzesco Castle Art Library. Visitors have rated this library an average of 4.6 out of 5 stars in 68,714 reviews.

Parco Sempione is another unique site you can experience today. This attraction is a park rated an average of 4.6 out of 5 stars in 72,914 reviews.

Make your way to the fantastic Arch of Peace, perhaps the most famous monument in Milan. This attraction is rated 4.6 out of 5 stars by 27,502 travelers.

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

After savoring a delicious meal, step into the vibrant nightlife at BhangraBar, where the evening is just getting started. In the same way, Rufus Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Ostello Bello Grande is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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

After soaking in Milan’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Fidenza. Expect your car journey to take a minimum of 1 hour 22 min. When you arrive in Fidenza, it's time to take a break from the road.

Make Cathedral of Fidenza one of your first sightseeing stops in Fidenza. Rated an average of 4.6 out of 5 stars by 535 travelers, a visit to this local attraction makes for a great introduction to the area.

Fasten your seatbelt and make your way to your next stop. Fidenza, 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 Milan to Fidenza may take around 1 hour 22 min without traffic disruptions. Upon arrival in Fidenza, we highly recommend checking out some of the top attractions.

Journey into the unknown at Pinacoteca di Brera, a unique attraction awaiting your visit. This remarkable art museum has an average rating of 4.7 out of 5 stars from 26,077 reviews. Every year, Pinacoteca di Brera welcomes more than 417 curious visitors.

When you’re ready to continue your sightseeing, Museo della Scienza e della Tecnologia "Leonardo da Vinci" is a recommended place to visit. This technology museum is rated an average of 4.5 out of 5 stars in 22,235 reviews. Based on recent data, the attraction hosts 532,084 visitors per year.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to JEFFER cocktails & friends, known for its inviting atmosphere. Le Parisien Wine Bar is another great option if you’re looking for a place to get the night started. Similarly, Las Volta cocktailbar provides a great setting to enjoy the night away.

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

On day 14 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

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 in Perugia, we highly recommend checking out some of the top attractions.

Begin your sightseeing with a visit to Knights' Square. This extraordinary square is rated an average of 4.5 out of 5 stars by 9,051 visitors.

Next, make your way to Leaning Tower of Pisa. This top attraction is a bell tower with an average rating of 4.7 out of 5 stars by 116,882 visitors. Leaning Tower of Pisa welcomes 3,200,000 yearly visitors.

We also recommend a visit to Pisa Cathedral. This cathedral is rated 4.8 out of 5 stars by 8,361 travelers.

If you’re keen to keep exploring, visit Piazza del Duomo, Pisa. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 104,550 travelers.

Today is also your chance to spend some time at Campo santo. This cemetery is rated an average of 4.6 out of 5 stars by 586 travelers.

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

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

Keep the evening going at Caffè Fortebraccio, a great choice for enjoying the after-dinner hours with a drink. You could also go to Caffe Del Banco, which offers a similarly pleasant setting and great drinks. Another option is Dempsey's Perugia, which provides an inviting environment for unwinding after a busy day 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.

Today is the last day of your 15-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 Perugia before saying goodbye.

Maximize your last day in Italy and go on a shopping spree in Perugia’s shopping center. This bustling commercial district is conveniently located near your lodging, granting you leisure time to roam and explore its assortment of establishments.

If you love the adrenaline rush of hunting for the best offers and deals in Italy, you’re in for a treat. A variety of goods and gifts await your discovery. Bring a bit of Italy home with you through these charming souvenirs.

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

Treat yourself to a delightful dinner at Sangallo Palace Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria a Priori? It's another excellent option with a diverse menu.

You will then say farewell to Perugia 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!