Luxury 7-Day Italy Road Trip from Pisa to Milan, Florence, and Rome and surrounding area

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!

Start your sightseeing with a visit to Logge dei Banchi. This sightseeing destination is a popular stop on travelers’ itineraries in Pisa, with an average rating of 4.2 out of 5 stars by 1,128 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.

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

Let the evening flow smoothly from dinner to drinks at JEFFER cocktails & friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta cocktailbar offers a memorable night with diverse drink options and excellent service.

Raise a toast to the start of your 7-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. 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 Milan. This drive usually takes around 3 hours 12 min, without any stops or traffic disruptions.

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.

Next up, make a stop at Leaning Tower of Pisa. With an average rating of 4.7 out of 5 stars by 116,882 visitors, it's easy to understand why so many people visit this bell tower every year. In fact, this attraction welcomes 3,200,000 annual visitors.

Pisa Cathedral is another attraction you can visit on this day of your vacation. This cathedral has an average rating of 4.8 out of 5 stars by 8,361 visitors.

When you’re finished at Pisa Cathedral, the perfect next stop is Piazza del Duomo, Pisa. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.

If you’re keen to explore even more, then consider a visit to Campo santo. This cemetery is a top place to visit, with a rating of 4.6 out of 5 stars from 586 reviews.

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

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

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated it is an ideal choice for italian contemporary and modern cuisine in the city.

Keep the excitement of the evening going by going to a bar or two. Nottingham Forest is an excellent place to start. You could also check out Armani/Bamboo Bar, offering a different kind of charm. A last recommendation for the day is Mag Cafe. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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. 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, Florence. This car ride takes around 3 hours 35 min.

Journey into the unknown at Duomo di Milano Museum, a unique attraction awaiting your visit. This remarkable art museum has an average rating of 4.8 out of 5 stars from 138,554 reviews. Every year, Duomo di Milano Museum welcomes more than 341,609 curious visitors.

When you’re ready to continue your sightseeing, Galleria Vittorio Emanuele II is a recommended place to visit. This commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

Another must-see attraction in Milan is Sforzesco Castle Art Library. Rated an average of 4.6 out of 5 stars by 68,714 travelers, this popular tourist destination in Milan offers an experience you will remember.

Parco Sempione is another popular stop on travelers' itineraries in Milan. This park promises memorable moments of exploring. Other travelers have rated this attraction 4.6 out of 5 stars in 72,914 reviews.

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.

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. SE·STO on Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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

Kick off the day at Cathedral of Santa Maria del Fiore, a top pick for today’s sightseeing. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Today is also your chance to visit Ponte Vecchio. Ponte Vecchio is a deck arch bridge with an average rating of 4.7 out of 5 stars from 118,099 reviews.

Piazzale Michelangelo is another top attraction we highly recommend you visit today. This square is rated an average of 4.8 out of 5 stars by 77,744 visitors.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Vatican City.

Start your sightseeing with a visit to St. Peter's Basilica. This major basilica is rated an average of 4.8 out of 5 stars from 131,043 visitors. St. Peter's Basilica welcomes around 11,000,000 visitors every year.

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

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.

Experience a taste of local culinary excellence while in Rome by securing a table at La Pergola. Esteemed as a 3-star Michelin restaurant, it features an exceptional mediterranean and contemporary menu. For an alternative taste experience, visit Il Pagliaccio, famous for its scrumptious creative and innovative dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Enoteca La Torre, a local favorite celebrated for its exquisite mediterranean and creative cuisine in Rome. Located in the heart of the city, this 2-star Michelin restaurant is an ideal pick for mediterranean and creative cuisine lovers seeking top-notch culinary experiences.

Let the evening flow smoothly from dinner to drinks at La Botticella of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Sant' Eustachio Caffè provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

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 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 1 night nights remaining.

Seize the day by visiting some of the best attractions in the area, like Colosseum. This extraordinary roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 visitors. Each year, around 7,400,000 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Roman Forum. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

While in Rome, we also recommend a visit to Pantheon. Hosting around 30,000,000 visitors every year, Pantheon is one of the best places to visit. This roman temple has been rated an average of 4.8 out of 5 stars in 189,682 reviews.

If you’re keen to explore even more, then consider a visit to Piazza Navona. With an average rating of 4.7 out of 5 stars by 158,771 travelers, this square is a highly recommended stop on your sightseeing around Rome.

Make your way to Castel Sant'Angelo, perhaps the most famous museum in Rome. This attraction welcomes around 918,591 visitors annually and is rated an average of 4.7 out of 5 stars in 72,431 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 Rome.

With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Cap off your dinner by heading to The Apartment Bar Roma, ideal for a leisurely evening with a drink in hand. Hotel Hassler Roma is another bar that offers an enjoyable setting.

Reminisce about your day, look through photos, and prepare for another great day to come! Your stress-free luxury holiday in Italy has plenty more in store for you.

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome. 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 Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 3 hours 44 min. When you arrive in Pisa, it's time to take a break from the road.

When you’re ready for some sightseeing, make your way to Trevi Fountain. This much-appreciated sculpture is rated 4.8 out of 5 stars in 343,494 reviews.

Next up is Piazza di Spagna. This square has an average rating of 4.7 out of 5 stars from 113,658 visitors.

Another top sightseeing recommendation is piazza del Popolo. This square has been rated 4.6 out of 5 stars in 89,807 reviews.

Foro Italico is another attraction you have the opportunity to visit today. This point of interest has an average rating of 4.6 out of 5 stars from 25,438 reviews.

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

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

Following your dinner, dive into the local bar culture at Bar Mocambo. Alternatively, go to Tree, the perfect place for those looking to experience the best of the nightlife. Similarly, Chupiteria provides excellent drinks and a great atmosphere, ensuring a memorable 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.

Today is the last day of your 7-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.

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

Whether you’re on a hunt for an ideal present to give to your friends or family or looking for a personal memento to remind you of Italy, a variety of items are waiting for you. Hold onto the magic of Italy with these wonderful souvenirs, ensuring your memories never fade.

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!