Luxury 13-Day Italy Road Trip from Pisa traveling south to Siena, Rome, Naples, 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!

Start your sightseeing with a visit to Knights' Square. This square is a popular stop on travelers’ itineraries in Pisa, with an average rating 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.

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.

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 13-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 Siena, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Pisa and Cascine Vecchie.

Seize the day by visiting some of the best attractions in the area, like Leaning Tower of Pisa. This extraordinary bell tower has an average rating of 4.7 out of 5 stars from 116,882 visitors. Each year, around 3,200,000 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Battistero di San Giovanni. This church is rated an average of 4.6 out of 5 stars in 1,894 reviews.

While in Pisa, we also recommend a visit to Piazza del Duomo, Pisa. This square has been 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 Pisa Cathedral. With an average rating of 4.8 out of 5 stars by 8,361 travelers, this cathedral is a highly recommended stop on your sightseeing around Pisa.

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

Journey into the unknown at Parco Regionale Migliarino, San Rossore, Massaciuccoli, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.4 out of 5 stars from 9,632 reviews.

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

Discover a world of culinary delights in Siena, 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.

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

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena 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.

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Siena and 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.

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.

Start your sightseeing with a visit to Sistine Chapel. This chapel is rated an average of 4.7 out of 5 stars from 52,083 visitors.

St. Peter's Basilica is another popular attraction you could visit today. This major basilica has a rating of 4.8 out of 5 stars from 131,043 visitors. St. Peter's Basilica attracts up to 11,000,000 visitors every year.

Vatican Museums is also highly recommended by travelers. More than 1,612,530 people visit this top attraction every year. This art museum has a rating of 4.6 out of 5 stars from 133,310 visitors.

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

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

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Continue the enjoyment post-dinner at La Botticella of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Sant' Eustachio Caffè offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffè Portofino. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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 3 nights nights remaining.

Kick off the day at Foro Italico, a top pick for today’s sightseeing. This point of interest is rated an average of 4.6 out of 5 stars in 25,438 reviews.

Today is also your chance to visit piazza del Popolo. Piazza del Popolo is a square with an average rating of 4.6 out of 5 stars from 89,807 reviews.

Villa Borghese is another top attraction we highly recommend you visit today. This urban zone of rome is rated an average of 4.6 out of 5 stars by 69,749 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Basilica di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars by 27,678 visitors.

Lastly, don’t miss out on Archbasilica of St. John Lateran, a famous catholic cathedral in Rome. This attraction is rated an average of 4.8 out of 5 stars by 21,370 travelers.

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.

Continue your lively evening at The Apartment Bar Roma, a perfect place for winding down or revving up the night, depending on which mood you’re in. Hotel Hassler Roma is another excellent bar that offers a great selection of drinks to suit any mood.

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

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 2 nights nights remaining.

Make Spanish Steps one of your first sightseeing stops in Rome. Rated an average of 4.5 out of 5 stars by 57,211 travelers, a visit to this local attraction makes for a great introduction to the area.

Piazza di Spagna is a worthwhile attraction you can visit next. This square is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 113,658 reviews.

Today is also the perfect opportunity to drop by Trevi Fountain. This sculpture has been rated an average of 4.8 out of 5 stars by 343,494 visitors.

If you’re keen to explore more, head to Pantheon and find out why 30,000,000 people visit this spot every year. A trip to this popular roman temple is also your opportunity to see if it lives up to the reputable 4.8 out of 5-star rating as given by 189,682 previous visitors.

Another top place to visit is Piazza Navona. This square enjoys an average rating of 4.7 out of 5 stars from 158,771 local and international travelers.

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.

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 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 1 night nights remaining.

Begin your sightseeing with a visit to Altare della Patria. This architectural structure gets 1,683,070 visitors each year and is rated an average of 4.8 out of 5 stars in 49,843 reviews.

Next up, make your way to Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 reviews.

When you’re ready for your next sight of the day, continue to Colosseum. This roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 visitors. Up to 7,400,000 people visit this place of interest annually.

Beyond the above-mentioned attractions, you also have the opportunity to visit Circus Maximus. This circus is rated an average of 4.4 out of 5 stars by 44,741 visitors.

If you’re keen to explore even more, then consider a visit to Orange Garden. This park is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 17,939 visitors.

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

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!

Wake up to day 7 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Rome and Pompei. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

A top pick for your self-guided sightseeing tour today is largo di Torre Argentina. Previous visitors have rated this square an average of 4.5 out of 5 stars in 30,433 reviews.

Campo de' Fiori is a local recommendation that you also can pay a visit today. This square is rated an average of 4.4 out of 5 stars in 51,133 reviews.

Another attraction you won't want to miss is Castel Sant'Angelo. This museum is rated an average of 4.7 out of 5 stars in 72,431 reviews. Every year, around 918,591 travelers visit this site to discover its unique features.

After soaking in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pompei. Expect your car journey to take a minimum of 2 hours 35 min. When you arrive in Pompei, it's time to take a break from the road.

Seize the day by visiting some of the best attractions in the area, like Archaeological Park of Pompeii. This extraordinary museum has an average rating of 4.7 out of 5 stars from 49,465 visitors.

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

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

Experience a symphony of flavors at Il Comandante in Naples by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Il Comandante delights its guests with its exceptional variety of meals showcasing delicious creative and mediterranean cuisine. For a palate-pleasing alternative, make sure to dine at ARIA, acclaimed for its delectable contemporary and modern specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Veritas, a top-rated restaurant known for its outstanding menu. Known as a top-rated , it's a top choice for campanian and contemporary cuisine in the city.

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

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 8 of your luxury road trip in Italy begins and concludes in the city of Naples. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Naples, where you still have 1 night nights remaining.

Journey into the unknown at Castel Sant'Elmo, a unique attraction awaiting your visit. This remarkable castle has an average rating of 4.6 out of 5 stars from 25,314 reviews.

When you’re ready to continue your sightseeing, Naples National Archaeological Museum is a recommended place to visit. This archaeological museum is rated an average of 4.6 out of 5 stars in 27,352 reviews. Based on recent data, the attraction hosts 616,878 visitors per year.

Another must-see attraction in Naples is Cappella Sansevero. This spectacular former church gets over 175,138 visitors every year. Rated an average of 4.7 out of 5 stars by 25,405 travelers, this popular tourist destination in Naples offers an experience you will remember.

Ovo Castle is another popular stop on travelers' itineraries in Naples. This sightseeing destination promises memorable moments of exploring. Other travelers have rated this attraction 4.6 out of 5 stars in 33,595 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 Naples. Savor the local cuisine and relax as you recount the day's experiences.

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

After your meal, keep the night alive at a bar like Archivio Storico - Cocktail Bar & Wonderfood, known for its lively atmosphere. Babette Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Gran Caffè Cimmino 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 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 Perugia, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Naples and Caserta.

Begin your sightseeing with a visit to piazza del Plebiscito. This extraordinary square is rated an average of 4.7 out of 5 stars by 58,141 visitors.

Next, make your way to Castel Nuovo. This top attraction is a castle with an average rating of 4.4 out of 5 stars by 28,032 visitors.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Caserta. This drive usually takes around 43 min, without any stops or traffic disruptions.

Your sightseeing of the day begins at Palace of Caserta, a remarkable mountain park where it’s easy to get lost in exploration. This top attraction is rated an average of 4.6 out of 5 stars in 36,840 reviews. Each year, this popular place of interest welcomes approximately 296,577 visitors.

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

After enjoying a fulfilling meal, continue your evening at Tommi Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Valentina offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffe Dal Perugino 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.

On day 10 of your luxury holiday in Italy, your road trip route will take you exploring the best of Santa Maria degli Angeli and Perugia. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Kick off the day at Rocca Paolina, a top pick for today’s sightseeing. This rocca is rated an average of 4.7 out of 5 stars in 7,128 reviews.

Today is also your chance to visit Carducci Gardens. Carducci Gardens is a park with an average rating of 4.5 out of 5 stars from 1,768 reviews.

Piazza IV Novembre is another top attraction we highly recommend you visit today. This square is rated an average of 4.6 out of 5 stars by 9,189 visitors.

When you’ve had your share of Perugia, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Santa Maria degli Angeli. Your travel time is around 32 min.

Take the opportunity to see Basilica of San Francesco d'Assisi. This attraction has an average rating of 4.9 out of 5 stars from 33,258 visitors.

Fasten your seatbelt and make your way to your next stop. Santa Maria degli Angeli, 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 Santa Maria degli Angeli to Santa Maria degli Angeli may take around 9 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

Begin your sightseeing with a visit to Basilica of Santa Maria degli Angeli. This papal basilica is rated an average of 4.8 out of 5 stars in 19,258 reviews.

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

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

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds , and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

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.

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

Day 11 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.

Make Ponte Vecchio your first stop of the day. Previous visitors have rated this deck arch bridge an average of 4.7 out of 5 stars in 118,099 reviews.

Next up, make a stop at Uffizi Gallery. With an average rating of 4.7 out of 5 stars by 61,794 visitors, it's easy to understand why so many people visit this national museum every year. In fact, this attraction welcomes 2,011,219 annual visitors.

Piazza della Signoria is another attraction you can visit on this day of your vacation. This square has an average rating of 4.8 out of 5 stars by 66,956 visitors.

When you’re finished at piazza della Signoria, the perfect next stop is Basilica of Santa Croce in Florence. This church is rated an average of 4.7 out of 5 stars in 28,544 reviews.

If you’re keen to explore even more, then consider a visit to piazzale Michelangelo. This square is a top place to visit, with a rating of 4.8 out of 5 stars from 77,744 reviews.

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

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

Journey into the unknown at Cathedral of Santa Maria del Fiore, a unique attraction awaiting your visit. This remarkable church has an average rating of 4.8 out of 5 stars from 76,359 reviews.

When you’re ready to continue your sightseeing, Galleria dell'Accademia is a recommended place to visit. This national museum is rated an average of 4.6 out of 5 stars in 34,429 reviews. Based on recent data, the attraction hosts 1,719,645 visitors per year.

Another must-see attraction in Florence is Central Market. Rated an average of 4.4 out of 5 stars by 43,100 travelers, this popular tourist destination in Florence offers an experience you will remember.

Basilica di Santa Maria Novella, Firenze (FI) is another popular stop on travelers' itineraries in Florence. This archives promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 23,075 reviews.

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

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

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.

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 13-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 your final day in Italy unfolds, don’t miss the chance for a last-minute shopping spree in Pisa’s best shopping location. Your accommodation’s convenient location near the city’s shopping area offers the luxury of time, so you don’t have to limit yourself from leisurely strolling its streets amidst a collection of establishments.

Look for the perfect gift for your loved ones back home, or buy yourself a little keepsake to remind you of Italy. Keep the spirit of your trip to Italy alive with these special souvenirs.

Make the most of what's left of your luxury vacation and head out to the stunning Logge dei Banchi. This extraordinary point of interest 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!