Luxury One-Week Italy Road Trip from Pisa to Milan, Florence, and Rome and surrounding area

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Escape for the holiday of a lifetime with this 8-day luxury road trip in Italy!

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned vacation itinerary, you will stay 2 nights in Pisa, 3 nights in Milan, 1 night in Florence, and 1 night in Rome, experiencing the ultimate luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 8-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.

Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 8-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.

Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. Here you can find unique souvenirs to preserve the memory of your luxury holiday in Italy.

This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 8-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.

To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Pisa, Milan, Florence, and Rome at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best flights, activities, tours, and hotels in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your luxury holiday in Italy today!

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Day 1

Day 1 – Pisa - arrival day

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

Take the opportunity to see “tuttomondo” (keith Haring). This attraction has an average rating of 4.6 out of 5 stars from 1,937 visitors.

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.

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

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Baribaldi Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Restaurant -Pizzeria Il Mio Capriccio, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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 8-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Pisa, and Milan

  • Milan
  • Pisa
  • More

Drive 291 km, 3 hours 47 min

  • Piazza del Duomo
  • Camposanto
  • Cattedrale di Pisa
  • Leaning Tower of Pisa
  • Piazza dei Cavalieri
  • More

Wake up to day 2 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 3 nights. The day's itinerary unfolds with a diverse array of experiences in Pisa.

Kick off the day at Piazza Del Duomo, Pisa, a top pick for today’s sightseeing. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.

Today is also your chance to visit Campo Santo. Campo Santo is a cemetery with an average rating of 4.6 out of 5 stars from 586 reviews.

Pisa Cathedral is another top attraction we highly recommend you visit today. This cathedral is rated an average of 4.8 out of 5 stars by 8,361 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Leaning Tower Of Pisa. This bell tower is rated an average of 4.7 out of 5 stars by 116,882 visitors. Visiting Leaning Tower Of Pisa means you'll be one of 3,200,000 people who do so every year.

Lastly, don’t miss out on Knights' Square, a famous square in Pisa. This attraction is rated an average of 4.5 out of 5 stars by 9,051 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Experience a taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international, and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary, and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary, and modern cuisine lovers seeking top-notch culinary experiences.

Round off your dining experience by visiting Nottingham Forest, a prime location for a drink. Alternatively, explore the distinctive characteristics of Armani/bamboo Bar, a bar catering to every mood and preference. Mag Cafe likewise offers a unique atmosphere, perfect for a memorable night out.

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.

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Day 3

Day 3 – Milan

  • Milan
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Drive 7 km, 31 min

  • Duomo di Milano
  • Palazzo Reale di Milano
  • Teatro alla Scala
  • Galleria Vittorio Emanuele II
  • Cathedral Square
  • More

Day 3 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.

When you're ready to see some sights, Duomo Di Milano Museum is a great place to start. This art museum is rated an average of 4.8 out of 5 stars by 138,554 visitors. Duomo Di Milano Museum attracts more than 341,609 visitors every year.

Another popular attraction you can visit today is Royal Palace Of Milan. This art museum has an average rating of 4.6 out of 5 stars from 17,538 travelers.

We also recommend a stop at La Scala. The opera house has been rated an average of 4.7 out of 5 stars by 26,219 visitors.

If you're keen to explore more, consider visiting Galleria Vittorio Emanuele Ii. This commercial gallery is a popular attraction with an average rating of 4.7 out of 5 stars from 91,394 reviews.

Cathedral Square is another easily accessible place to visit on this day of your trip. Stop by this point of interest, rated 4.8 out of 5 stars in 7,539 reviews, to discover more of what makes it unique.

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

Treat yourself to a wonderful meal at Nero 9, a top-rated dining spot in Milan. If you're in the mood for something new, try Ristorante la Brisa, another premier location with a delectable menu. You might also want to book a table at UNAHOTELS Cusani Milano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

Let the evening flow smoothly from dinner to drinks at Kilburn Cocktail Bar Milano, a top-rated bar in the area. For other recommendations, Bar Frida provides a perfect setting for rounding out your night with style and great drinks. Likewise, The Friends Pub Milano 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!

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Day 4

Day 4 – Milan

  • Milan
  • More

Drive 12 km, 53 min

  • Pinacoteca di Brera
  • Sforzesco Castle
  • Sempione Park
  • Arco della Pace
  • Piazza Gae Aulenti
  • More

Day 4 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.

Seize the day by visiting some of the best attractions in the area, like Pinacoteca Di Brera. This extraordinary art museum has an average rating of 4.7 out of 5 stars from 26,077 visitors. Each year, around 417 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Sforzesco Castle Art Library. This library is rated an average of 4.6 out of 5 stars in 68,714 reviews.

While in Milan, we also recommend a visit to Parco Sempione. This park has been rated an average of 4.6 out of 5 stars in 72,914 reviews.

If you’re keen to explore even more, then consider a visit to Arch Of Peace. With an average rating of 4.6 out of 5 stars by 27,502 travelers, this monument is a highly recommended stop on your sightseeing around Milan.

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

Discover a world of culinary delights in Milan, 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.

Treat yourself to a delicious dinner at Vento di Sardegna, an excellent option for tonight's dining. Looking for something different? Palazzo Parigi Hotel & Grand Spa Milano offers a tantalizing alternative with its diverse menu. And don’t miss Galleria Restaurant. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

Continue your evening by exploring the vibrant nightlife scene at Bhangrabar, a prime destination for a thrilling night out. Also, don’t forget to check out Rufus Cocktail Bar, a bar that offers unique local touches. Likewise, Ostello Bello Grande provides an excellent alternative for a fun evening.

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

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Day 5

Day 5 – Milan, and Florence

  • Florence
  • Milan
  • More

Drive 324 km, 4 hours 8 min

  • Santa Maria delle Grazie
  • Leonardo da Vinci Museum of Science and Technology
  • Basilica di Sant'Ambrogio
  • Rotonda della Besana
  • More

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

Seize the day by visiting some of the best attractions in the area, like Santa Maria Delle Grazie Church. This extraordinary convent has an average rating of 4.5 out of 5 stars from 13,490 visitors.

Next, make your way to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This technology museum welcomes around 532,084 visitors yearly and is rated an average of 4.5 out of 5 stars in 22,235 reviews.

While in Milan, we also recommend a visit to Basilica Di Sant'ambrogio. This church has been rated an average of 4.7 out of 5 stars in 12,883 reviews.

If you’re keen to explore even more, then consider a visit to Rotonda Della Besana. With an average rating of 4.4 out of 5 stars by 2,614 travelers, this sightseeing destination is a highly recommended stop on your sightseeing around Milan.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative, and mediterranean 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 Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary, and international menu. With a 1-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 Florence.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the 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.

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Day 6

Day 6 – Florence, Vatican City, and Rome

  • Rome
  • More

Drive 283 km, 3 hours 32 min

  • Vatican Museums
  • Sistine Chapel
  • Saint Peter's Square
  • St Peter's Basilica
  • More

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. The day's journey will conclude in Rome, 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’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 Vatican City, Vatican City. Your travel time is around 3 hours 11 min.

A top pick for your self-guided sightseeing tour today is Vatican Museums. Over 1,612,530 travelers visit this attraction every year. Previous visitors have rated this art museum an average of 4.6 out of 5 stars in 133,310 reviews.

Sistine Chapel is a local recommendation that you also can pay a visit today. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Another attraction you won't want to miss is Saint Peter's Square. This square is rated an average of 4.8 out of 5 stars in 38,954 reviews.

St. Peter's Basilica is another outstanding experience in Vatican City. Around 131,043 travelers have rated this major basilica an average of 4.8 out of 5 stars. The attraction hosts 11,000,000 visitors annually.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Rome. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Experience a symphony of flavors at La Pergola in Rome by securing a reservation in advance. Renowned for its 3-star Michelin distinction, La Pergola delights its guests with its exceptional variety of meals showcasing delicious mediterranean, and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Il Pagliaccio, acclaimed for its delectable creative, and innovative specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Enoteca La Torre, a top-rated restaurant known for its outstanding menu. Known as a top-rated 2-star Michelin establishment, it's a top choice for mediterranean, and creative cuisine in the city.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Sant' Eustachio Caffè offers a unique charm perfect for experiencing the local bar scene in Rome. Caffè Portofino 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.

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Day 7

Day 7 – Rome, and Pisa

  • Pisa
  • Rome
  • More

Drive 370 km, 4 hours 34 min

  • Roman Forum
  • Colosseum
  • Trevi Fountain
  • More

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

Begin your sightseeing with a visit to Roman Forum. This extraordinary square is rated an average of 4.7 out of 5 stars by 114,450 visitors.

Next, make your way to Colosseum. This top attraction is a roman amphitheatre with an average rating of 4.7 out of 5 stars by 328,821 visitors. Colosseum welcomes 7,400,000 yearly visitors.

We also recommend a visit to Trevi Fountain. This sculpture is rated 4.8 out of 5 stars by 343,494 travelers.

If you’re keen to keep exploring, visit Foro Italico. This highly recommended sightseeing destination has received an average rating of 4.6 out of 5 stars from 25,438 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Pisa. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Make sure to book a table at Ristorante alle Bandierine, a popular restaurant in Pisa. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Pisa at Barrique Cocktail And Bistrot, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is Filter Coffee Lab. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Pisa tonight.

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

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

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Day 8

Day 8 – Pisa - departure day

  • Pisa - Departure day
  • More

Today is the last day of your 8-day luxury holiday in Italy and it’s soon time to start your journey home. This is your chance to get one last glimpse of Pisa before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Make the most of what's left of your luxury vacation and head out to the stunning Lungarni Di Pisa. This extraordinary sightseeing destination and attraction is rated an average of 4.6 out of 5 stars in 662 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.

If you're in the mood for something new, try Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. , another premier location with a delectable menu.

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!

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