Luxury 10-Day Italy Road Trip from Pisa traveling south to Florence, Rome, and Arezzo

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 for some sightseeing, make your way to Logge dei Banchi. This much-appreciated sightseeing destination is rated 4.2 out of 5 stars in 1,128 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.

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 JEFFER cocktails & friends, a well-loved spot among locals and tourists. Or, head to Le Parisien Wine Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Las Volta cocktailbar, another top-rated place in the area.

Raise a toast to the start of your 10-day luxury vacation in Italy and look forward to more fantastic days to come!

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

Continue your road trip and head to your next destination, Florence. This car ride takes around 1 hour 28 min.

Journey into the unknown at Knights' Square, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.5 out of 5 stars from 9,051 reviews.

When you’re ready to continue your sightseeing, Leaning Tower of Pisa is a recommended place to visit. This bell tower is rated an average of 4.7 out of 5 stars in 116,882 reviews. Based on recent data, the attraction hosts 3,200,000 visitors per year.

Another must-see attraction in Pisa is Piazza del Duomo, Pisa. Rated an average of 4.7 out of 5 stars by 104,550 travelers, this popular tourist destination in Pisa offers an experience you will remember.

Pisa Cathedral is another popular stop on travelers' itineraries in Pisa. This cathedral promises memorable moments of exploring. Other travelers have rated this attraction 4.8 out of 5 stars in 8,361 reviews.

Continue your road trip and head to your next destination, Cascine Vecchie.

Start your sightseeing with a visit to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This park is rated an average 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.

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

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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of SE·STO on Arno Rooftop Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

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 1 night nights remaining.

Begin your sightseeing with a visit to piazzale Michelangelo. This extraordinary square is rated an average of 4.8 out of 5 stars by 77,744 visitors.

Next, make your way to Uffizi Gallery. This top attraction is a national museum with an average rating of 4.7 out of 5 stars by 61,794 visitors. Uffizi Gallery welcomes 2,011,219 yearly visitors.

We also recommend a visit to Ponte Vecchio. This deck arch bridge is rated 4.7 out of 5 stars by 118,099 travelers.

If you’re keen to keep exploring, visit piazza della Signoria. This highly recommended sightseeing destination has received an average rating of 4.8 out of 5 stars from 66,956 travelers.

Today is also your chance to spend some time at Cathedral of Santa Maria del Fiore. This church is rated an average of 4.8 out of 5 stars by 76,359 travelers.

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.

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Orvieto. This drive usually takes around 1 hour 54 min, without any stops or traffic disruptions.

Seize the day by visiting some of the best attractions in the area, like Orvieto Cathedral. This extraordinary catholic cathedral has an average rating of 4.8 out of 5 stars from 15,057 visitors.

Next, make your way to Orvieto Underground. This archaeological site welcomes around 37,000 visitors yearly and is rated an average of 4.6 out of 5 stars in 1,517 reviews.

While in Orvieto, we also recommend a visit to Pozzo della Cava. Hosting around 20,336 visitors every year, Pozzo della Cava is one of the best places to visit. This objet du musée d'archéologie has been rated an average of 4.6 out of 5 stars in 1,403 reviews.

As you’ve unraveled the marvels of Florence, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Orvieto may take around 1 hour 54 min. Upon your arrival in Orvieto, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you’re ready for some sightseeing, make your way to Well of St. Patrick. This much-appreciated sightseeing destination is rated 4.5 out of 5 stars in 14,274 reviews.

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 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 , 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.

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 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 3 nights nights remaining.

Journey into the unknown at Basilica di Santa Maria Maggiore, a unique attraction awaiting your visit. This remarkable major basilica has an average rating of 4.8 out of 5 stars from 27,678 reviews.

When you’re ready to continue your sightseeing, Colosseum is a recommended place to visit. This roman amphitheatre is rated an average of 4.7 out of 5 stars in 328,821 reviews. Based on recent data, the attraction hosts 7,400,000 visitors per year.

Another must-see attraction in Rome is Roman Forum. Rated an average of 4.7 out of 5 stars by 114,450 travelers, this popular tourist destination in Rome offers an experience you will remember.

Largo di Torre Argentina is another popular stop on travelers' itineraries in Rome. This square promises memorable moments of exploring. Other travelers have rated this attraction 4.5 out of 5 stars in 30,433 reviews.

Lastly, don't miss out on Pantheon. Rated 4.8 out of 5 stars by 189,682 local and international travelers, it's a popular place to visit. This roman temple gets closer to 30,000,000 visits every year.

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

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

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

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 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.

When you’re ready for some sightseeing, make your way to Circus Maximus. This much-appreciated circus is rated 4.4 out of 5 stars in 44,741 reviews.

Next up is Altare della Patria. This architectural structure has an average rating of 4.8 out of 5 stars from 49,843 visitors. As one of the top places to visit in the city, Altare della Patria welcomes 1,683,070 visitors annually.

Another top sightseeing recommendation is Trevi Fountain. This sculpture has been rated 4.8 out of 5 stars in 343,494 reviews.

Piazza di Spagna is another attraction you have the opportunity to visit today. This square has an average rating of 4.7 out of 5 stars from 113,658 reviews.

To continue your sightseeing, head over to Spanish Steps. This monumental staircase is rated an average of 4.5 out of 5 stars in 57,211 reviews.

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

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

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

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.

Make Villa Borghese your first stop of the day. Previous visitors have rated this urban zone of rome an average of 4.6 out of 5 stars in 69,749 reviews.

Next up, make a stop at piazza del Popolo. With an average rating of 4.6 out of 5 stars by 89,807 visitors, it's easy to understand why so many people visit this square every year.

Castel Sant'Angelo is another attraction you can visit on this day of your vacation. This museum has an average rating of 4.7 out of 5 stars by 72,431 visitors. Up to 918,591 travelers come to Rome every year to see Castel Sant'Angelo with their own eyes.

When you’re finished at Castel Sant'Angelo, the perfect next stop is Piazza Navona. This square is rated an average of 4.7 out of 5 stars in 158,771 reviews.

If you’re keen to explore even more, then consider a visit to Campo de' Fiori. This square is a top place to visit, with a rating of 4.4 out of 5 stars from 51,133 reviews.

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.

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

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

On day 8 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

A top pick for your self-guided sightseeing tour today is St. Peter's Basilica. Over 11,000,000 travelers visit this attraction every year. Previous visitors have rated this major basilica an average of 4.8 out of 5 stars in 131,043 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.

Vatican Museums is another outstanding experience in Vatican City. Around 133,310 travelers have rated this art museum an average of 4.6 out of 5 stars. The attraction hosts 1,612,530 visitors annually.

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

Set out on a gastronomic journey in Arezzo by reserving a table at Octavin. Renowned for its , this restaurant presents an outstanding menu of creative cuisine. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Arezzo.

Following your dinner, dive into the local bar culture at Liquid Bar.

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 9 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 Siena and Livorno.

Set your GPS to Siena and hit the road. Expect a journey of approximately 1 hour 4 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

Start your sightseeing with a visit to piazza del Campo. This square is rated an average of 4.8 out of 5 stars from 64,175 visitors.

Siena Cathedral is another popular attraction you could visit today. This domus has a rating of 4.8 out of 5 stars from 21,656 visitors.

Fortezza Medicea (Siena) is also highly recommended by travelers. This fortress has a rating of 4.5 out of 5 stars from 9,835 visitors.

Fasten your seatbelt and make your way to your next stop. Livorno, 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 Siena to Livorno may take around 1 hour 55 min without traffic disruptions. Upon arrival in Livorno, we highly recommend checking out some of the top attractions.

Begin your sightseeing with a visit to Terrazza Mascagni. This seafront is rated an average of 4.6 out of 5 stars in 21,838 reviews.

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

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

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

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

Today is the last day of your 10-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.

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

Savor the flavors at Sud, a top pick for dinner tonight. Alternatively, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Beckons with its unique menu offerings.

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!