Luxury 14-Day Italy Road Trip from Pisa to Florence, Rome, Arezzo, Verona, and Milan and surrounding area

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

Make Knights' Square your first stop of the day. Previous visitors have rated this square an average of 4.5 out of 5 stars in 9,051 reviews.

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

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

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

After enjoying a fulfilling meal, continue your evening at JEFFER cocktails & friends, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Le Parisien Wine Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Las Volta cocktailbar provides an excellent environment for a relaxed and enjoyable evening.

Raise a toast to the start of your 14-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 Pisa and Cascine Vecchie. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Begin your sightseeing with a visit to Leaning Tower of Pisa. This bell tower gets 3,200,000 visitors each year and is rated an average of 4.7 out of 5 stars in 116,882 reviews.

Next up, make your way to Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 reviews.

When you’re ready for your next sight of the day, continue to Battistero di San Giovanni. This church has an average rating of 4.6 out of 5 stars from 1,894 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Pisa Cathedral. This cathedral is rated an average of 4.8 out of 5 stars by 8,361 visitors.

Upon your arrival in Cascine Vecchie, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Seize the day by visiting some of the best attractions in the area, like Parco Regionale Migliarino, San Rossore, Massaciuccoli. This extraordinary park has an average rating of 4.4 out of 5 stars from 9,632 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 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 Florence so you can check out the menus and make advance reservations.

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative and mediterranean cuisine. Another highly-recommended restaurant in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant , known for its delicious italian contemporary and international menu.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, SE·STO on Arno Rooftop Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 3 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 2 nights nights remaining.

When you’re ready for some sightseeing, make your way to Ponte Vecchio. This much-appreciated deck arch bridge is rated 4.7 out of 5 stars in 118,099 reviews.

Next up is Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars from 61,794 visitors. As one of the top places to visit in the city, Uffizi Gallery welcomes 2,011,219 visitors annually.

Another top sightseeing recommendation is piazza della Signoria. This square has been rated 4.8 out of 5 stars in 66,956 reviews.

Basilica of Santa Croce in Florence is another attraction you have the opportunity to visit today. This church has an average rating of 4.7 out of 5 stars from 28,544 reviews.

To continue your sightseeing, head over to piazzale Michelangelo. This square is rated an average of 4.8 out of 5 stars in 77,744 reviews.

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

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

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

Day 4 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.

Start your sightseeing with a visit to Basilica di Santa Maria Novella, Firenze (FI). This archives is rated an average of 4.7 out of 5 stars from 23,075 visitors.

Central Market is another popular attraction you could visit today. This sightseeing destination has a rating of 4.4 out of 5 stars from 43,100 visitors.

Cathedral of Santa Maria del Fiore is also highly recommended by travelers. This church has a rating of 4.8 out of 5 stars from 76,359 visitors.

Galleria dell'Accademia is an attraction you won’t want to miss. Around 1,719,645 people visit this place every year. This national museum is rated an average of 4.6 out of 5 stars in 34,429 reviews.

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.

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 5 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.

Continue your road trip and head to your next destination, Vatican City.

An excellent attraction to start your day with is Vatican Museums. This art museum typically receives around 1,612,530 visitors every year and is rated an average of 4.6 out of 5 stars in 133,310 reviews.

Continue your journey at Sistine Chapel. This chapel is rated 4.7 out of 5 stars by 52,083 travelers from near and far.

Vatican City is also the home of Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 visitors.

You can continue your self-guided sightseeing tour at St. Peter's Basilica. A total of 11,000,000 people explore this attraction every year. Rated 4.8 out of 5 stars by 131,043 visitors, a visit to this top sight is time well spent.

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

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.

Continue your lively evening at La Botticella of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Sant' Eustachio Caffè is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino 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.

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 2 nights nights remaining.

Drop by the renowned Basilica di Santa Maria Maggiore. This popular major basilica has been rated an average of 4.8 out of 5 stars by 27,678 visitors.

Another unforgettable place to experience is Colosseum. Rated 4.7 out of 5 stars by 328,821 visitors, this roman amphitheatre deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Roman Forum. This square has been rated an average of 4.7 out of 5 stars in 114,450 reviews.

Another favorite attraction in the area is Altare della Patria, drawing over 1,683,070 yearly visitors. This architectural structure and popular place of interest enjoys a rating of 4.8 out of 5 stars from 49,843 local and international travelers.

If you’re keen to explore even more, then consider a visit to largo di Torre Argentina. With an average rating of 4.5 out of 5 stars from 30,433 travelers, this square is an attraction many avid travelers highly recommend visiting while in Rome.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

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 7 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 Circus Maximus. This extraordinary circus is rated an average of 4.4 out of 5 stars by 44,741 visitors.

Next, make your way to Pantheon. This top attraction is a roman temple with an average rating of 4.8 out of 5 stars by 189,682 visitors. Pantheon welcomes 30,000,000 yearly visitors.

We also recommend a visit to Piazza Navona. This square is rated 4.7 out of 5 stars by 158,771 travelers.

If you’re keen to keep exploring, visit Campo de' Fiori. This highly recommended sightseeing destination has received an average rating of 4.4 out of 5 stars from 51,133 travelers.

Today is also your chance to spend some time at Castel Sant'Angelo. This museum is rated an average of 4.7 out of 5 stars by 72,431 travelers. It’s estimated that 918,591 people visit this fantastic attraction every year.

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.

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

Wake up to day 8 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.

Start your sightseeing with a visit to Trevi Fountain. This sculpture is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.8 out of 5 stars by 343,494 visitors.

Piazza di Spagna is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 113,658 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Spanish Steps. Visitors have rated this monumental staircase an average of 4.5 out of 5 stars in 57,211 reviews.

Piazza del Popolo is another unique site you can experience today. This attraction is a square rated an average of 4.6 out of 5 stars in 89,807 reviews.

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

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

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

Discover the culinary delights of Arezzo by securing a reservation at Octavin. Esteemed for its , this restaurant offers a remarkable selection of creative cuisine.

Cap off your dinner by heading to Liquid Bar, ideal for a leisurely evening with a drink in hand.

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

On day 9 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.

After soaking in Arezzo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Bologna. Expect your car journey to take a minimum of 2 hours 11 min. When you arrive in Bologna, it's time to take a break from the road.

Your sightseeing of the day begins at Piazza Santo Stefano, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 7,617 reviews.

Next, satisfy your wanderlust at Two Towers. This tower has an average rating of 4.7 out of 5 stars from 25,975 travelers.

Piazza Maggiore is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 64,523 travelers, 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 Palazzo Re Enzo. This well-loved palazzo boasts a 4.6 out of 5-star rating from 2,072 reviews.

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

Discover a world of culinary delights in Verona, 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.

Have a memorable dining experience in Verona by booking a table at Casa Perbellini 12 Apostoli, renowned as a 2-star Michelin restaurant presenting an exceptional creative and contemporary menu. For a different culinary experience, Il Desco shines as one of the top destinations known for its delicious italian contemporary cuisine in Verona. This 1-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, Osteria Mondo d'Oro is known as a top local spot for its delicious italian and seasonal cuisine in Verona. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

After enjoying a fulfilling meal, continue your evening at Archivio, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, La Segreteria Café offers a welcoming atmosphere for easing into the nightlife. Similarly, Duchi Café provides an excellent environment for a relaxed and enjoyable evening.

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

Start your sightseeing with a visit to Verona Arena. This opera house is rated an average of 4.7 out of 5 stars from 123,818 visitors. Verona Arena welcomes around 195,540 visitors every year.

When you’ve had your share of Verona, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Valeggio sul Mincio. Your travel time is around 50 min.

When you're ready to see some sights, Parco Giardino Sigurtà is a great place to start. This park is rated an average of 4.6 out of 5 stars by 27,387 visitors.

Set your GPS to Ronchi and hit the road. Expect a journey of approximately 31 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Ronchi beckons with new experiences!

Make Gardaland Resort your first stop of the day. Previous visitors have rated this amusement park an average of 4.4 out of 5 stars in 99,291 reviews.

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

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

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Unwind after your meal by stepping into Nottingham Forest. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Armani/Bamboo Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Mag Cafe, another top-rated bar in the area.

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

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.

Start your sightseeing with a visit to Royal Palace of Milan. This art museum is a popular stop on travelers’ itineraries in Milan, with an average rating of 4.6 out of 5 stars by 17,538 visitors.

Duomo di Milano Museum is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 138,554 reviews gives you an idea of other visitors’ experience at this attraction. It’s estimated that around 341,609 people visit this art museum every year.

If it’s still bright and early, make your way to Galleria Vittorio Emanuele II. Visitors have rated this commercial gallery an average of 4.7 out of 5 stars in 91,394 reviews.

La Scala is another unique site you can experience today. This attraction is an opera house rated an average of 4.7 out of 5 stars in 26,219 reviews.

Make your way to the fantastic Piazza Gae Aulenti, perhaps the most famous square in Milan. This attraction is rated 4.6 out of 5 stars by 30,398 travelers.

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

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

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 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.

A top pick for your self-guided sightseeing tour today is Museo della Scienza e della Tecnologia "Leonardo da Vinci". Over 532,084 travelers visit this attraction every year. Previous visitors have rated this technology museum an average of 4.5 out of 5 stars in 22,235 reviews.

Arch of Peace is a local recommendation that you also can pay a visit today. This monument is rated an average of 4.6 out of 5 stars in 27,502 reviews.

Another attraction you won't want to miss is Parco Sempione. This park is rated an average of 4.6 out of 5 stars in 72,914 reviews.

Sforzesco Castle Art Library is another outstanding experience in Milan. Around 68,714 travelers have rated this library an average of 4.6 out of 5 stars.

If you long for more, Pinacoteca di Brera is not far away. This art museum is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.7 out of 5 stars in 26,077 reviews.

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.

Round off your dining experience by visiting BhangraBar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Rufus Cocktail Bar, a bar catering to every mood and preference. Ostello Bello Grande likewise offers a unique atmosphere, perfect for a memorable night out.

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 La Spezia.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in La Spezia. This drive usually takes around 2 hours 47 min, without any stops or traffic disruptions.

Begin your sightseeing with a visit to Castello San Giorgio. This extraordinary castle is rated an average of 4.4 out of 5 stars by 2,452 visitors.

Next, make your way to Giardini Pubblici. This top attraction is a park with an average rating of 4.1 out of 5 stars by 2,364 visitors.

We also recommend a visit to Technical Naval Museum of Spezia. This museum is rated 4.5 out of 5 stars by 1,561 travelers.

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

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

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

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.

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 Pisa before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Thanks to your accommodation’s strategic location, the city’s bustling commercial district is only a stone’s throw away, giving you ample time to leisurely explore the area, filled with local shops.

Take time to find the perfect present, reminding you of the charms of Italy. Each store here is brimming with unique finds. These souvenirs will help you treasure your memories of Italy forever.

Make the most of what's left of your luxury vacation and head out to the stunning Logge dei Banchi. This extraordinary sightseeing destination and attraction is rated an average of 4.2 out of 5 stars in 1,128 reviews, and is an excellent choice for your last sightseeing in Pisa.

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

You will then say farewell to Pisa 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!