Luxury Two-Week Italy Self-Drive Road Trip With Itinerary from Naples traveling north to Viterbo, Florence, Bologna, Milan, Pisa, Arezzo, and Rome

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 1 night remaining.

Naples is brimming with adventures. Today’s wonderful stops include a church, a cave system, and a museum. Begin your sightseeing adventure at the well-known Cattedrale Di Santa Maria Assunta. Just a short distance away is Napoli Sotterranea Percorso Ufficiale, a photogenic cave system that draws visitors from far and near.

Continue your journey to Cappella Sansevero, one of the city’s most popular spots that you shouldn’t miss. Another great site to visit is the interesting Chiesa Del Gesù Nuovo.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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.

Start your culinary exploration in Naples by securing a reservation at Il Comandante. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative and mediterranean cuisine. For another dining delight, visit ARIA, celebrated for its delectable contemporary and modern menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Veritas, a top local spot known for its tantalizing campanian and contemporary menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Archivio Storico - Cocktail Bar & Wonderfood, known for its inviting atmosphere. Archeobar is another great option if you’re looking for a place to get the night started. Similarly, Babette Pub provides a great setting to enjoy the night away.

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

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Naples and Tivoli. The day's journey will conclude in Viterbo, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Brace yourself for today’s incredible lineup of attractions in Naples, featuring a gorgeous, a photogenic, a standout, a culturally significant, and a remarkable. Start at Castel Nuovo, a notable castle in the city. Then, head to Naples National Archaeological Museum and soak in the ambiance of this detailed museum.

Set your GPS to Tivoli and hit the road. Expect a journey of approximately 2 hours 12 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Tivoli beckons with new experiences!

Spend your afternoon discovering Hadrian's Villa, an up-and-coming archeological site known for its awe-inspiring features.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Viterbo. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Discover a world of culinary delights in Viterbo, 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.

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

Day 5 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 remaining.

Florence is home to plenty of attractions that offer an instagrammable, a historically significant, a profound, a culturally significant, a romantic, a stunning, an UNESCO world heritage-listed, and a masterful! Start at Basilica Of Santa Croce In Florence, a captivating church that is worthwhile a visit in the city. Nearby, you’ll find Cathedral Of Santa Maria Del Fiore, enchanting visitors with its romantic appeal. Continue your exploration at Galleria Dell'accademia. This art gallery is one of the city’s most well-known spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Central Market. After exploring the food market, head to the globally renowned Ponte Vecchio. This historical landmark will wrap up today’s self-guided sightseeing tour in the city.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night 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.

Wake up to day 6 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 Bologna, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

Today’s itinerary in Florence covers several incredible sights, including a public square, a palace, an art gallery, an observation deck and much more! Start your adventure at Piazza Della Signoria. This widely recognized public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Palazzo Vecchio, a must-see palace in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Uffizi Gallery. This astonishing art gallery offers an enriching experience. For a change of pace, head to Piazzale Michelangelo, where you can take in its romantic features.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Bologna. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Enjoy an outstanding dining experience at I Portici, a 1-star Michelin restaurant offering an exceptional creative and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby Bib Gourmand-awardee, Ahimè, known for its delicious country cooking cuisine. Another highly-recommended restaurant in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant, known for its delicious emilian menu.

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

On day 7 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna and Verona. The day's journey will conclude in Milan, a city that offers you comfort and relaxation for 2 nights. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Bologna is brimming with adventures. Today’s wonderful stops include a monument and a public square. Begin your sightseeing adventure at the well-known Two Towers. Just a short distance away is Piazza Maggiore, a romantic public square that draws visitors from far and near.

Fasten your seatbelt and make your way to your next stop. Verona, 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 Bologna to Verona may take around 1 hour 47 min without traffic disruptions. Upon arrival in Verona, we highly recommend checking out some of the top attractions.

Make your way to Castelvecchio Museum, a well-known museum that draws attention for its breathtaking features. Spend some time soaking in the atmosphere before continuing to Verona Arena, an enchanting stadium that stands out in the city.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international and contemporary dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Let the evening flow smoothly from dinner to drinks at Nottingham Forest, a top-rated bar in the area. For other recommendations, Armani/bamboo Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Mag Cafe offers a memorable night with diverse drink options and excellent service.

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

Day 8 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 remaining.

Set out on a day brimming with a breathtaking, a visually striking, a history-steeped, a grand, a charming, a scenic, a remarkable, and a stunning. Start at the locally renowned Piazza Gae Aulenti, a visually striking public square in Milan. Next, go to Pinacoteca Di Brera.

After visiting Piazza Gae Aulenti and Pinacoteca Di Brera, take time to explore Milan's streets and absorb its charm. Continue your sightseeing by heading to Sforzesco Castle Art Library. This breathtaking castle offers a unique experience. Parco Sempione is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Arch Of Peace, one of the most picture-perfect places to visit in Milan.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

Discover a world of culinary delights in Milan, 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.

Make sure to reserve a table at Dessert Bar Milano, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Radisson Blu Hotel Milan, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Qui Si Mangia, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Kilburn Cocktail Bar Milano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Frida, the perfect place for those looking to experience the best of the nightlife. Similarly, The Friends Pub Milano provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Reminisce about your day, look through photos, and prepare for another great day to come! Your luxury holiday in Italy has plenty more in store for you.

Wake up to day 9 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Milan and Genoa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start by visiting Cathedral Square, a prime spot to begin your journey. This enchanting public square is sure to impress. Next on your list is Galleria Vittorio Emanuele Ii, another must-visit landmark and impressive shopping mall renowned for its awe-inspiring features.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Genoa. This drive usually takes around 1 hour 58 min, without any stops or traffic disruptions.

Spiaggia Pubblica Di Priaruggia is an increasingly popular beach we recommend making time to visit today. Discover its eye-catching features before continuing your self-guided tour.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Pisa. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Enjoy a lovely meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, il Mercante is another top choice with a popular menu. You could also check for a table at La Ghiotteria. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Jeffer Cocktails & Friends, known for its inviting atmosphere. Le Parisien Wine Bar is another great option if you’re looking for a place to get the night started. Similarly, Las Volta Cocktailbar provides a great setting to enjoy the night away.

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 10 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 Arezzo, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Pisa.

Start your day at Knights' Square. This culturally significant public square is an up-and-coming place to see in Pisa. Then, wander over to Leaning Tower Of Pisa. If UNESCO world heritage-listed sites excite you, this monument will be right up your alley. Nearby, you’ll also find Angelo Caduto.

Pisa offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Del Duomo, Pisa is a wondrous spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the historic Pisa Cathedral. Take a moment to appreciate the fascinating details of this intriguing church in Pisa.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Arezzo. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Begin your culinary exploration in Arezzo by securing a reservation at Octavin. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine. Or, for a change of pace, La Clandestina boasts a menu that's sure to impress.

Keep the excitement of the evening going by visiting a bar or two. Liquid Bar is an excellent place to start.

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

On day 11 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. The day's journey will conclude in Rome, a city that offers you comfort and relaxation for 3 nights. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Immerse yourself in Vatican City’s rich culture with today's sightseeing itinerary.

Embrace the thrill of the open road as you wave goodbye to Arezzo and set your GPS to Vatican City, Vatican City. 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 2 hours 32 min. Upon reaching Vatican City, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Head to Vatican Museums, a world-famous art museum in Vatican City. This impressive chapel is a top recommendation in the area. When you’re ready to explore more, Saint Peter's Square is an excellent choice. Next, continue your sightseeing at the wondrous St. Peter's Basilica and discover what makes this major basilica unique.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Rome. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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.

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.

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Almalu Trastevere is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Viminale Di Pepi Maurilio 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.

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 remaining.

Get ready to discover some of the most iconic wonders in Rome, including an archeological site and a monument. Start your day at Circus Maximus. This stunning archeological site is a captivating place to see in Rome. Then, wander over to Colosseum. If picture-perfect sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Roman Forum. This culturally significant archeological site is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Largo Di Torre Argentina is a locally renowned spot in the city that will captivate you with its unique charm. When you’re done at the archeological site, don’t forget to check out the photogenic Pantheon. Take a moment to appreciate the fascinating details of this world-famous monument in Rome.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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 remaining.

Prepare for a day full of a charming, a peaceful, a breathtaking, an eye-catching, a historic, a noteworthy, and a grand. When you’re ready, kick off your sightseeing adventure at Villa Borghese. This astonishing park is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Popolo, one of the city’s most promising highlights.

Next, check out Castel Sant'angelo, one of the most top-rated places to see in Rome. This castle is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Navona. Wander around and soak in the enchanting atmosphere this public square offers. Finally, take the path to the spectacular Campo De' Fiori, the last of our attraction recommendations for today.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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.

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

Today’s route brings an enchanting, a picture-perfect, a historically significant, a majestic, a detailed, a charming, a monumental, and an UNESCO world heritage-listed. The first attraction of today is Altare Della Patria. This locally renowned monument is a historic place to see in Rome. Continue your discovery at Spanish Steps, a visually striking public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Di Spagna. This wondrous public square offers a history-steeped encounter with Rome. Basilica Di Santa Maria Maggiore is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Naples. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Don’t miss out on dining at Opera Restaurant, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Trattoria San Ferdinando, another top spot with a mouthwatering menu. You might also want to secure a reservation at Anonymous Trattoria Gourmet. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.

Continue your lively evening at Gran Caffè Cimmino, a perfect place for winding down or revving up the night, depending on which mood you’re in. Flanagan's Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Napoli ensures a night out tailored to your taste.

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.