Luxury One-Week Italy Road Trip from Pisa traveling south to Arezzo, Rome, Perugia, and Florence

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!

When you're ready to see some sights, Knights' Square is a great place to start. This square is rated an average of 4.5 out of 5 stars by 9,051 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.

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

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

Following your dinner, dive into the local bar culture at JEFFER cocktails & friends. Alternatively, go to Le Parisien Wine Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Las Volta cocktailbar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise a toast to the start of your 8-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 Pisa and Cascine Vecchie. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

As you’ve unraveled the marvels of Pisa, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Arezzo may take around 1 hour 57 min. Upon your arrival in Arezzo, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Drop by the renowned Leaning Tower of Pisa. This popular bell tower has been rated an average of 4.7 out of 5 stars by 116,882 visitors. Based on recent data, this attraction is visited by more than 3,200,000 travelers every year.

Another unforgettable place to experience is Piazza del Duomo, Pisa. Rated 4.7 out of 5 stars by 104,550 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Battistero di San Giovanni. This church has been rated an average of 4.6 out of 5 stars in 1,894 reviews.

Another favorite attraction in the area is Pisa Cathedral. This cathedral and popular place of interest enjoys a rating of 4.8 out of 5 stars from 8,361 local and international travelers.

Upon reaching Cascine Vecchie, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Be one of the day’s first visitors at Parco Regionale Migliarino, San Rossore, Massaciuccoli. This park is rated an average of 4.4 out of 5 stars by 9,632 visitors.

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

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

Get ready for an unforgettable culinary journey in Arezzo by reserving a table at Octavin. Renowned as a 1-star Michelin restaurant, it offers an exceptional creative menu.

Continue your lively evening at Liquid Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in.

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 3 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 Vatican City.

Vatican City welcomes you with a multitude of unique vacation experiences.

When you’re ready for some sightseeing, make your way to Vatican Museums. This much-appreciated art museum is rated 4.6 out of 5 stars in 133,310 reviews. Each year, 1,612,530 people visit this site to admire its unique features.

Next up is Sistine Chapel. This chapel has an average rating of 4.7 out of 5 stars from 52,083 visitors.

Another top sightseeing recommendation is Saint Peter's Square. This square has been rated 4.8 out of 5 stars in 38,954 reviews.

St. Peter's Basilica is another attraction you have the opportunity to visit today. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 reviews. This popular attraction gets 11,000,000 visits every year.

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

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.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds , and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

After your meal, keep the night alive at a bar like La Botticella of Poggi Giovanni, known for its lively atmosphere. Sant' Eustachio Caffè is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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 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 1 night nights remaining.

Your sightseeing of the day begins at Colosseum, a remarkable roman amphitheatre where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 328,821 reviews. Each year, this popular place of interest welcomes approximately 7,400,000 visitors.

Next, satisfy your wanderlust at Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 travelers.

Pantheon is another must-visit attraction. This renowned roman temple offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 189,682 travelers and attracting 30,000,000 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 Piazza Navona. This well-loved square boasts a 4.7 out of 5-star rating from 158,771 reviews.

When there’s still energy left for exploring, Castel Sant'Angelo awaits. If you’ve been interested in experiencing a museum, this is a top pick rated 4.7 out of 5 stars by 72,431 previous visitors. Each year, approximately 918,591 people travel to Rome to experience it.

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.

Esteemed as a restaurant, it features an exceptional menu.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

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 5 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.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Perugia. Your travel time is around 2 hours 12 min.

Kick off the day at Altare della Patria, a top pick for today’s sightseeing. Attracting approximately 1,683,070 visits every year, this attraction is a must-see. This architectural structure is rated an average of 4.8 out of 5 stars in 49,843 reviews.

Today is also your chance to visit Trevi Fountain. Trevi Fountain is a sculpture with an average rating of 4.8 out of 5 stars from 343,494 reviews.

Piazza di Spagna is another top attraction we highly recommend you visit today. This square is rated an average of 4.7 out of 5 stars by 113,658 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit piazza del Popolo. This square is rated an average of 4.6 out of 5 stars by 89,807 visitors.

Lastly, don’t miss out on Villa Borghese, a famous urban zone of rome in Rome. This attraction is rated an average of 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 Perugia.

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

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

Cap off your dinner by heading to Tommi Bar, ideal for a leisurely evening with a drink in hand. Valentina is another bar that offers an enjoyable setting. Similarly, Caffe Dal Perugino is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Wake up to day 6 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Siena and Santa Maria degli Angeli. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

After soaking in Santa Maria degli Angeli’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 38 min. When you arrive in Siena, it's time to take a break from the road.

Start your sightseeing with a visit to piazza del Campo. This square is a popular stop on travelers’ itineraries in Siena, with an average rating of 4.8 out of 5 stars by 64,175 visitors.

Siena Cathedral is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 21,656 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Fortezza Medicea (Siena). Visitors have rated this fortress an average of 4.5 out of 5 stars in 9,835 reviews.

As you’ve unraveled the marvels of Perugia, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Santa Maria degli Angeli may take around 32 min. Upon your arrival in Santa Maria degli Angeli, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Start your sightseeing with a visit to Basilica of San Francesco d'Assisi. This papal basilica is rated an average of 4.9 out of 5 stars from 33,258 visitors.

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

Discover a world of culinary delights in Florence, 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.

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean 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 Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. SE·STO on Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

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 Florence.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 13 min. When you arrive, enjoy some sightseeing.

Journey into the unknown at piazza della Signoria, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.8 out of 5 stars from 66,956 reviews.

When you’re ready to continue your sightseeing, Cathedral of Santa Maria del Fiore is a recommended place to visit. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Another must-see attraction in Florence is Ponte Vecchio. Rated an average of 4.7 out of 5 stars by 118,099 travelers, this popular tourist destination in Florence offers an experience you will remember.

Uffizi Gallery is another popular stop on travelers' itineraries in Florence. This national museum promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 61,794 reviews. Each year, approximately 2,011,219 people travel to visit Uffizi Gallery.

Lastly, don't miss out on piazzale Michelangelo. Rated 4.8 out of 5 stars by 77,744 local and international travelers, it's a popular place to visit.

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

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

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 stress-free luxury holiday in Italy has plenty more in store for you.

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.

Maximize your last day in Italy and go on a shopping spree in Pisa’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 Pisa one last time before you head to the airport.

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

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!