Luxury 14-Day Italy Road Trip from Brindisi traveling west to Province of Salerno, Rome, Florence, Milan, Arezzo, and Naples

Your luxury holiday in Italy begins as soon as you reach the city of Brindisi, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Take the opportunity to see End of the Via Appia Antica. This attraction has an average rating of 4.6 out of 5 stars from 1,744 visitors.

Tonight, you will be treated to a stay at one of the best luxury hotels in Brindisi. 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 Brindisi.

Esteemed as a restaurant, it features an exceptional menu.

Let the evening flow smoothly from dinner to drinks at Peddy Bar. Pasticceria. Gelateria. Happyhour. Prodotti celiaci. Slot machines. Scommesse, a top-rated bar in the area. For other recommendations, Eden Cafè provides a perfect setting for rounding out your night with style and great drinks. Likewise, Altair Cafè offers a memorable night with diverse drink options and excellent service.

Raise a toast to the start of your 14-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 Province of Salerno, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Brindisi and Francavilla Fontana.

Francavilla Fontana’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Brindisi behind. This drive usually takes around 31 min. Francavilla Fontana welcomes you with a multitude of unique vacation experiences.

Seize the day by visiting some of the best attractions in the area, like Swabian Castle of Brindisi. This extraordinary point of interest has an average rating of 4.4 out of 5 stars from 382 visitors.

Next, make your way to Cillarese Park. This park is rated an average of 4.4 out of 5 stars in 1,169 reviews.

After soaking in Brindisi’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Francavilla Fontana. Expect your car journey to take a minimum of 31 min. When you arrive in Francavilla Fontana, it's time to take a break from the road.

Your sightseeing of the day begins at Castello di Francavilla Fontana, a remarkable point of interest where it’s easy to get lost in exploration. This top attraction is rated an average of 4.5 out of 5 stars in 685 reviews.

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

Discover a world of culinary delights in Province of Salerno, 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 Re Maurì, a 1-star Michelin restaurant offering an incredible creative menu. As a top-rated it is an ideal choice in the city.

If you’re not ready to end the night just yet, Hilton Bar e Gastronomia offers a perfect venue to relax and savor a drink. Similarly, The Black Monday speakeasy TBM is well-suited for those looking to unwind in a social setting. Dòmo i' vinaino Wine Bar - Enogastronomia is another excellent spot to enjoy a nightcap after a delightful meal.

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

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 Vatican City. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Fasten your seatbelt and make your way to your next stop. Vatican City, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Start your sightseeing with a visit to Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars from 133,310 visitors. Vatican Museums welcomes around 1,612,530 visitors every year.

Sistine Chapel is another popular attraction you could visit today. This chapel has a rating of 4.7 out of 5 stars from 52,083 visitors.

St. Peter's Basilica is also highly recommended by travelers. More than 11,000,000 people visit this top attraction every year. This major basilica has a rating of 4.8 out of 5 stars from 131,043 visitors.

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

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

Have a memorable dining experience in Rome by booking a table at La Pergola, renowned as a 3-star Michelin restaurant presenting an exceptional mediterranean and contemporary menu. For a different culinary experience, Il Pagliaccio shines as one of the top destinations known for its delicious creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Enoteca La Torre is known as a top local spot for its delicious mediterranean and creative cuisine in Rome. This 2-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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.

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 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 2 nights nights remaining.

Start your sightseeing with a visit to Basilica di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars from 27,678 visitors.

Colosseum is another popular attraction you could visit today. This roman amphitheatre has a rating of 4.7 out of 5 stars from 328,821 visitors. Colosseum attracts up to 7,400,000 visitors every year.

Roman Forum is also highly recommended by travelers. This square has a rating of 4.7 out of 5 stars from 114,450 visitors.

Altare della Patria is an attraction you won’t want to miss. Around 1,683,070 people visit this place every year. This architectural structure is rated an average of 4.8 out of 5 stars in 49,843 reviews.

Another attraction you have the opportunity to visit today is largo di Torre Argentina. This square has received an average rating of 4.5 out of 5 stars from 30,433 travelers.

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.

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

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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 1 night nights remaining.

Begin your sightseeing with a visit to Circus Maximus. This circus is rated an average of 4.4 out of 5 stars in 44,741 reviews.

Next up, make your way to Pantheon. This roman temple has an average rating of 4.8 out of 5 stars from 189,682 reviews. Usually, around 30,000,000 people visit Pantheon every year.

When you’re ready for your next sight of the day, continue to Piazza Navona. This square has an average rating of 4.7 out of 5 stars from 158,771 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 Castel Sant'Angelo. This museum is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 72,431 visitors. Approximately 918,591 travelers visit Castel Sant'Angelo every year.

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.

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

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.

Continue your road trip and head to your next destination, Florence. This car ride takes around 3 hours 4 min.

Start your sightseeing with a visit to Trevi Fountain. This sculpture is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.8 out of 5 stars by 343,494 visitors.

Piazza di Spagna is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 113,658 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Spanish Steps. Visitors have rated this monumental staircase an average of 4.5 out of 5 stars in 57,211 reviews.

Piazza del Popolo is another unique site you can experience today. This attraction is a square rated an average of 4.6 out of 5 stars in 89,807 reviews.

Make your way to the fantastic Villa Borghese, perhaps the most famous urban zone of rome in Rome. This attraction is rated 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 Florence.

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.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its , this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to SE·STO on Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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 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.

A top pick for your self-guided sightseeing tour today is piazzale Michelangelo. Previous visitors have rated this square an average of 4.8 out of 5 stars in 77,744 reviews.

Uffizi Gallery is a local recommendation that you also can pay a visit today. This national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. The attraction welcomes 2,011,219 visitors every year.

Another attraction you won't want to miss is Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Piazza della Signoria is another outstanding experience in Florence. Around 66,956 travelers have rated this square an average of 4.8 out of 5 stars.

If you long for more, Cathedral of Santa Maria del Fiore is not far away. This church is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.8 out of 5 stars in 76,359 reviews. The attraction gets an estimated 2,011,219 visitors every year.

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.

Esteemed as a restaurant, it features an exceptional menu.

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 1 hour 12 min, without any stops or traffic disruptions.

An excellent attraction to start your day with is Leaning Tower of Pisa. This bell tower typically receives around 3,200,000 visitors every year and is rated an average of 4.7 out of 5 stars in 116,882 reviews.

Continue your journey at Piazza del Duomo, Pisa. This square is rated 4.7 out of 5 stars by 104,550 travelers from near and far.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 1 hour 12 min.

Start your sightseeing with a visit to Basilica di Santa Maria Novella, Firenze (FI). This archives is rated an average of 4.7 out of 5 stars from 23,075 visitors.

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

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

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Unwind after your meal by stepping into Nottingham Forest. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Armani/Bamboo Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Mag Cafe, another top-rated bar in the area.

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

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

Kick off the day at Royal Palace of Milan, a top pick for today’s sightseeing. This art museum is rated an average of 4.6 out of 5 stars in 17,538 reviews.

Today is also your chance to visit Cathedral Square. Cathedral Square is a point of interest with an average rating of 4.8 out of 5 stars from 7,539 reviews.

Duomo di Milano Museum is another top attraction we highly recommend you visit today. This art museum is rated an average of 4.8 out of 5 stars by 138,554 visitors. In a single year, this art museum hosts approximately 341,609 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Galleria Vittorio Emanuele II. This commercial gallery is rated an average of 4.7 out of 5 stars by 91,394 visitors.

Lastly, don’t miss out on La Scala, a famous opera house in Milan. This attraction is rated an average of 4.7 out of 5 stars by 26,219 travelers.

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

Keep the evening going at Kilburn Cocktail Bar Milano, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Frida, which offers a similarly pleasant setting and great drinks. Another option is The Friends Pub Milano, 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.

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 Bologna and Milan. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Bologna. Your travel time is around 2 hours 30 min.

Journey into the unknown at Piazza Maggiore, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.7 out of 5 stars from 64,523 reviews.

Bologna’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Milan behind. This drive usually takes around 2 hours 30 min. Bologna welcomes you with a multitude of unique vacation experiences.

Make Sforzesco Castle Art Library your first stop of the day. Previous visitors have rated this library an average of 4.6 out of 5 stars in 68,714 reviews.

Next up, make a stop at Parco Sempione. With an average rating of 4.6 out of 5 stars by 72,914 visitors, it's easy to understand why so many people visit this park every year.

Piazza Gae Aulenti is another attraction you can visit on this day of your vacation. This square has an average rating of 4.6 out of 5 stars by 30,398 visitors.

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

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

Experience a taste of local culinary excellence while in Arezzo by securing a table at Octavin. Esteemed as a 1-star Michelin restaurant, it features an exceptional creative menu.

Continue your evening by exploring the vibrant nightlife scene at Liquid Bar, a prime destination for a thrilling 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.

On day 11 of your luxury holiday in Italy, your road trip route will take you exploring the best of Arezzo and Caserta. 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 Arezzo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Caserta. Expect your car journey to take a minimum of 3 hours 57 min. When you arrive in Caserta, it's time to take a break from the road.

Begin your sightseeing with a visit to piazza Grande. This square is rated an average of 4.6 out of 5 stars in 14,465 reviews.

Next up, make your way to Arezzo Cathedral. This cathedral has an average rating of 4.6 out of 5 stars from 2,450 reviews.

Embrace the thrill of the open road as you wave goodbye to Arezzo and set your GPS to Caserta. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 3 hours 57 min. Upon reaching Caserta, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready to see some sights, Palace of Caserta is a great place to start. This mountain park is rated an average of 4.6 out of 5 stars by 36,840 visitors. Palace of Caserta attracts more than 296,577 visitors every year.

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

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

Enjoy an outstanding dining experience at Il Comandante, a 1-star Michelin restaurant offering an exceptional creative and mediterranean menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 1-star Michelin-awardee, ARIA, known for its delicious contemporary and modern cuisine. Another highly-recommended restaurant in Naples is Veritas, a renowned restaurant , known for its delicious campanian and contemporary menu.

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

Day 12 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.

Make Ovo Castle one of your first sightseeing stops in Naples. Rated an average of 4.6 out of 5 stars by 33,595 travelers, a visit to this local attraction makes for a great introduction to the area.

Naples National Archaeological Museum is a worthwhile attraction you can visit next. This archaeological museum is a valued place of interest in the area, with an average rating of 4.6 out of 5 stars from 27,352 reviews. Up to 616,878 travelers visit this site every year to make their time in Naples special.

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 Napoli Sotterranea Percorso Ufficiale. A trip to this popular museum is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 19,274 previous visitors.

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

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

Keep the excitement of the evening going by going to a bar or two. Archivio Storico - Cocktail Bar & Wonderfood is an excellent place to start. You could also check out Babette Pub, offering a different kind of charm. A last recommendation for the day is Gran Caffè Cimmino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Set your GPS to Bari and hit the road. Expect a journey of approximately 2 hours 58 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bari beckons with new experiences!

Make Basilica di San Nicola your first stop of the day. Previous visitors have rated this cathedral an average of 4.8 out of 5 stars in 16,196 reviews. More than 445,000 people visit this place of interest every year.

As you’ve unraveled the marvels of Naples, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Bari may take around 2 hours 58 min. Upon your arrival in Bari, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make piazza del Plebiscito one of your first sightseeing stops in Naples. Rated an average of 4.7 out of 5 stars by 58,141 travelers, a visit to this local attraction makes for a great introduction to the area.

Castel Nuovo is a worthwhile attraction you can visit next. This castle is a valued place of interest in the area, with an average rating of 4.4 out of 5 stars from 28,032 reviews.

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

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

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 14-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 Brindisi before saying goodbye.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Brindisi’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 Brindisi 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 Brindisi 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!