Luxury Two-Week Italy Road Trip from Naples to Viterbo, Florence, Pisa, Arezzo, and Rome

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

Journey into the unknown at Ovo Castle, a unique attraction awaiting your visit. This remarkable point of interest has an average rating of 4.6 out of 5 stars from 33,595 reviews.

Tonight, you will be treated to a stay at one of the best luxury hotels in Naples. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

Discover a world of culinary delights in Naples, 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 an extraordinary dining experience at Il Comandante, a 1-star Michelin restaurant offering an incredible creative and mediterranean menu. Alternatively, if your taste buds call for something different, ARIA is one of the best restaurants for contemporary and modern cuisine in Naples. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Veritas. As a top-rated it is an ideal choice for campanian and contemporary cuisine in the city.

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

Raise a toast to the start of your 15-day luxury vacation in Italy and look forward to more fantastic days to come!

Day 2 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 3 nights nights remaining.

Make Cattedrale di Santa Maria Assunta one of your first sightseeing stops in Naples. Rated an average of 4.7 out of 5 stars by 14,592 travelers, a visit to this local attraction makes for a great introduction to the area.

Napoli Sotterranea Percorso Ufficiale is a worthwhile attraction you can visit next. This museum is a valued place of interest in the area, with an average rating of 4.6 out of 5 stars from 19,274 reviews.

Today is also the perfect opportunity to drop by Cappella Sansevero. This former church has been rated an average of 4.7 out of 5 stars by 25,405 visitors. Up to 175,138 people travel to this site annually.

If you’re keen to explore more, head to Naples National Archaeological Museum and find out why 616,878 people visit this spot every year. A trip to this popular archaeological museum is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 27,352 previous visitors.

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

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

After enjoying a fulfilling meal, continue your evening at Archivio Storico - Cocktail Bar & Wonderfood, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Babette Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Gran Caffè Cimmino provides an excellent environment for a relaxed and enjoyable evening.

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

Day 3 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 2 nights nights remaining.

Start your sightseeing with a visit to Certosa e Museo di San Martino. This museum is a popular stop on travelers’ itineraries in Naples, with an average rating of 4.5 out of 5 stars by 5,307 visitors.

Chiesa del Gesù Nuovo is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 16,437 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Castel Sant'Elmo. Visitors have rated this castle an average of 4.6 out of 5 stars in 25,314 reviews.

Complesso Monumentale di Santa Chiara is another unique site you can experience today. This attraction is a church rated an average of 4.7 out of 5 stars in 5,944 reviews.

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

Keep the evening going at Flanagan's Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Parthenope Bar, which offers a similarly pleasant setting and great drinks. Another option is Bar Gianni Unica sede dal 1970, which provides an inviting environment for unwinding after a busy day 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.

Day 4 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.

Seize the day by visiting some of the best attractions in the area, like Museo e Real Bosco di Capodimonte. This extraordinary museum has an average rating of 4.7 out of 5 stars from 10,608 visitors.

Next, make your way to Catacombs of San Gennaro. This cemetery welcomes around 35,000 visitors yearly and is rated an average of 4.7 out of 5 stars in 7,431 reviews.

While in Naples, we also recommend a visit to Palazzo Zevallos Stigliano. This building has been rated an average of 4.6 out of 5 stars in 3,615 reviews.

If you’re keen to explore even more, then consider a visit to Castel Nuovo. With an average rating of 4.4 out of 5 stars by 28,032 travelers, this castle is a highly recommended stop on your sightseeing around Naples.

Discover a world of culinary delights in Naples, 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.

Continue your lively evening at L'antiquario, 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 5 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Tivoli. 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, Tivoli. This car ride takes around 2 hours 25 min.

Kick off the day at Villa d'Este, a top pick for today’s sightseeing. Attracting approximately 139,855 visits every year, this attraction is a must-see. This giardino all'italiana is rated an average of 4.7 out of 5 stars in 25,000 reviews.

Today is also your chance to visit Fontana dell'Organo. Fontana dell'Organo is a sightseeing destination with an average rating of 4.6 out of 5 stars from 195 reviews.

Fontana dell'Ovato (o di Tivoli) is another top attraction we highly recommend you visit today. This sightseeing destination is rated an average of 4.8 out of 5 stars by 176 visitors.

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

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

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

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

Fasten your seatbelt and make your way to your next stop. Siena, 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 Viterbo to Siena may take around 2 hours 4 min without traffic disruptions. Upon arrival in Siena, we highly recommend checking out some of the top attractions.

When you're ready to see some sights, Fortezza Medicea (Siena) is a great place to start. This fortress is rated an average of 4.5 out of 5 stars by 9,835 visitors.

Another popular attraction you can visit today is piazza del Campo. This square has an average rating of 4.8 out of 5 stars from 64,175 travelers.

We also recommend a stop at Siena Cathedral. The domus has been rated an average of 4.8 out of 5 stars by 21,656 visitors.

If you're keen to explore more, consider visiting Santuario di Santa Caterina. This shrine is a popular attraction with an average rating of 4.6 out of 5 stars from 1,201 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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. Esteemed as a 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to SE·STO on Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 7 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.

Kick off the day at Basilica of Santa Croce in Florence, a top pick for today’s sightseeing. This church is rated an average of 4.7 out of 5 stars in 28,544 reviews.

Today is also your chance to visit piazza della Signoria. Piazza della Signoria is a square with an average rating of 4.8 out of 5 stars from 66,956 reviews.

Ponte Vecchio is another top attraction we highly recommend you visit today. This deck arch bridge is rated an average of 4.7 out of 5 stars by 118,099 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Uffizi Gallery. This national museum is rated an average of 4.7 out of 5 stars by 61,794 visitors. Visiting Uffizi Gallery means you'll be one of 2,011,219 people who do so every year.

Lastly, don’t miss out on piazzale Michelangelo, a famous square in Florence. This attraction is rated an average of 4.8 out of 5 stars by 77,744 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 Florence so you can check out the menus and make advance reservations.

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 8 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 2 nights. The day's itinerary unfolds with a diverse array of experiences in Florence.

After soaking in Florence’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 1 hour 8 min. When you arrive in Pisa, it's time to take a break from the road.

Begin your sightseeing with a visit to Cathedral of Santa Maria del Fiore. This extraordinary church is rated an average of 4.8 out of 5 stars by 76,359 visitors.

Next, make your way to Galleria dell'Accademia. This top attraction is a national museum with an average rating of 4.6 out of 5 stars by 34,429 visitors. Galleria dell'Accademia welcomes 1,719,645 yearly visitors.

We also recommend a visit to Central Market. This sightseeing destination is rated 4.4 out of 5 stars by 43,100 travelers.

If you’re keen to keep exploring, visit Basilica di Santa Maria Novella, Firenze (FI). This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 23,075 travelers.

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

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.

Round off your dining experience by visiting JEFFER cocktails & friends, a prime location for a drink. Alternatively, explore the distinctive characteristics of Le Parisien Wine Bar, a bar catering to every mood and preference. Las Volta cocktailbar likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 9 of your luxury road trip in Italy begins and concludes in the city of Pisa. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Pisa, where you still have 1 night nights remaining.

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.

Another popular attraction you can visit today is Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 travelers. Every year, 3,200,000 travelers come to experience this site to make the most of their time in Pisa.

We also recommend a stop at Piazza del Duomo, Pisa. The square has been rated an average of 4.7 out of 5 stars by 104,550 visitors.

If you're keen to explore more, consider visiting Pisa Cathedral. This cathedral is a popular attraction with an average rating of 4.8 out of 5 stars from 8,361 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 Pisa.

Explore the vibrant nightlife at Bar Mocambo after your meal, a hub for lively evenings and memorable moments. Or, head to Tree for a great selection of flavorful drinks and a charming setting. Furthermore, Chupiteria is perfect for those looking to extend their night with a touch of local flavor.

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

Wake up to day 10 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Arezzo. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Begin your sightseeing with a visit to Arezzo Cathedral. This extraordinary cathedral is rated an average of 4.6 out of 5 stars by 2,450 visitors.

Next, make your way to piazza Grande. This top attraction is a square with an average rating of 4.6 out of 5 stars by 14,465 visitors.

We also recommend a visit to San Francesco, Arezzo. Hosting 20,939 visitors every year, San Francesco, Arezzo is one of the most popular places to visit in Arezzo. This minor basilica is rated 4.6 out of 5 stars by 2,377 travelers.

If you’re keen to keep exploring, visit Santa Maria della Pieve. This highly recommended sightseeing destination has received an average rating of 4.8 out of 5 stars from 720 travelers.

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

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

Have a memorable dining experience in Arezzo by booking a table at Octavin, renowned as a 1-star Michelin restaurant presenting an exceptional creative menu.

After your meal, keep the night alive at a bar like Liquid Bar, known for its lively atmosphere.

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

On day 11 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.

Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make Vatican Museums one of your first sightseeing stops in Vatican City. Rated an average of 4.6 out of 5 stars by 133,310 travelers, a visit to this local attraction makes for a great introduction to the area. This art museum attracts 1,612,530 visitors every year.

Saint Peter's Square is a worthwhile attraction you can visit next. This square is a valued place of interest in the area, with an average rating of 4.8 out of 5 stars from 38,954 reviews.

Today is also the perfect opportunity to drop by Sistine Chapel. This chapel has been rated an average of 4.7 out of 5 stars by 52,083 visitors.

If you’re keen to explore more, head to St. Peter's Basilica and find out why 11,000,000 people visit this spot every year. A trip to this popular major basilica is also your opportunity to see if it lives up to the reputable 4.8 out of 5-star rating as given by 131,043 previous visitors.

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.

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.

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.

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 12 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 Piazza Navona your first stop of the day. Previous visitors have rated this square an average of 4.7 out of 5 stars in 158,771 reviews.

Next up, make a stop at Pantheon. With an average rating of 4.8 out of 5 stars by 189,682 visitors, it's easy to understand why so many people visit this roman temple every year. In fact, this attraction welcomes 30,000,000 annual visitors.

Trevi Fountain is another attraction you can visit on this day of your vacation. This sculpture has an average rating of 4.8 out of 5 stars by 343,494 visitors.

When you’re finished at Trevi Fountain, the perfect next stop is Basilica di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars in 27,678 reviews.

If you’re keen to explore even more, then consider a visit to Circus Maximus. This circus is a top place to visit, with a rating of 4.4 out of 5 stars from 44,741 reviews.

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.

After your meal, keep the night alive at a bar like The Apartment Bar Roma, known for its lively atmosphere. Hotel Hassler Roma is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

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

Day 13 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.

Take the opportunity to see Castel Sant'Angelo. This attraction has an average rating of 4.7 out of 5 stars from 72,431 visitors and gets around 918,591 visits every year.

Piazza di Spagna is another sightseeing hotspot in the area. This square has been rated an average of 4.7 out of 5 stars by 113,658 travelers.

Rome is also the home of Spanish Steps. Around 57,211 people have rated this monumental staircase an average of 4.5 out of 5 stars.

Another place you’ll want to visit is piazza del Popolo. With an average rating of 4.6 out of 5 stars from a total of 89,807 reviews, a visit to this square is a great idea.

This day of your vacation in Rome is also your chance to admire Villa Borghese. This must-visit urban zone of rome enjoys an average rating of 4.6 out of 5 stars from 69,749 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 Rome. Savor the local cuisine and relax as you recount the day's experiences.

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

Naples’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 2 hours 34 min. Naples welcomes you with a multitude of unique vacation experiences.

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

Next up, make your way to Altare della Patria. This architectural structure has an average rating of 4.8 out of 5 stars from 49,843 reviews. Usually, around 1,683,070 people visit Altare della Patria every year.

When you’re ready for your next sight of the day, continue to largo di Torre Argentina. This square has an average rating of 4.5 out of 5 stars from 30,433 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Campo de' Fiori. This square is rated an average of 4.4 out of 5 stars by 51,133 visitors.

If you’re keen to explore even more, then consider a visit to Colosseum. This roman amphitheatre is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 328,821 visitors. Approximately 7,400,000 travelers visit Colosseum every year.

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

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

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

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 15-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 Naples before saying goodbye.

As your final day in Italy unfolds, don’t miss the chance for a last-minute shopping spree in Naples’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.

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

Have a fantastic dining experience at Palazzo Petrucci Ristorante, a highly recommended choice for tonight's dinner. If you're looking to mix things up, The Penny Black offers an enticing alternative with its varied menu.

You will then say farewell to Naples 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!