Luxury Two-Week Italy Road Trip from Bologna traveling south to Milan, Pisa, Siena, Rome, and Florence

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Escape for the holiday of a lifetime with this 15-day luxury road trip in Italy!

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned vacation itinerary, you will stay 2 nights in Bologna, 3 nights in Milan, 1 night in Pisa, 1 night in Siena, 5 nights in Rome, and 2 nights in Florence, experiencing the ultimate luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 15-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.

Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 15-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.

Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. Here you can find unique souvenirs to preserve the memory of your luxury holiday in Italy.

This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 15-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.

To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Bologna, Milan, Genoa, Pisa, Siena, Rome, Arezzo, and Florence at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best flights, activities, tours, and hotels in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your luxury holiday in Italy today!

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Day 1

Day 1 – Bologna - arrival day

  • Bologna - Arrival day
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  • Piazza Maggiore
  • More

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

Seize the day by visiting some of the best attractions in the area, like Piazza Maggiore. This extraordinary square has an average rating of 4.7 out of 5 stars from 64,523 visitors.

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

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

Make sure to reserve a table at Sfoglia Rina, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Va Mo Là, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria dal Biassanot, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Bar Freud E Squisito, which offers the perfect atmosphere for a night out. Moreover, Osteria Del Sole is another popular option for a drink or two. Likewise, Macondo - Cocktail Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 2

Day 2 – Bologna, and Milan

  • Milan
  • Bologna
  • More

Drive 229 km, 3 hours 7 min

  • Two Towers
  • Piazza Santo Stefano
  • International Museum and Library of Music
  • More

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Begin your sightseeing with a visit to Two Towers. This tower is rated an average of 4.7 out of 5 stars in 25,975 reviews.

Next up, make your way to Villa Ghigi. This park has an average rating of 4.7 out of 5 stars from 2,035 reviews.

When you’re ready for your next sight of the day, continue to Piazza Santo Stefano. This square has an average rating of 4.8 out of 5 stars from 7,617 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit International Museum And Library Of Music. This music museum is rated an average of 4.5 out of 5 stars by 742 visitors. Visiting International Museum And Library Of Music means you'll be one of 13,413 people who do so every year.

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.

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

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international, and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary, and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Continue the enjoyment post-dinner at Nottingham Forest, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Armani/bamboo Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Mag Cafe. 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!

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Day 3

Day 3 – Milan

  • Milan
  • More

Drive 8 km, 42 min

  • Piazza Gae Aulenti
  • Duomo di Milano
  • Palazzo Reale di Milano
  • Galleria Vittorio Emanuele II
  • Teatro alla Scala
  • More

Day 3 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 2 nights nights remaining.

Make Piazza Gae Aulenti your first stop of the day. Previous visitors have rated this square an average of 4.6 out of 5 stars in 30,398 reviews.

Next up, make a stop at Duomo Di Milano Museum. With an average rating of 4.8 out of 5 stars by 138,554 visitors, it's easy to understand why so many people visit this art museum every year. In fact, this attraction welcomes 341,609 annual visitors.

Royal Palace Of Milan is another attraction you can visit on this day of your vacation. This art museum has an average rating of 4.6 out of 5 stars by 17,538 visitors.

When you’re finished at Royal Palace Of Milan, the perfect next stop is Galleria Vittorio Emanuele Ii. This commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

If you’re keen to explore even more, then consider a visit to La Scala. This opera house is a top place to visit, with a rating of 4.7 out of 5 stars from 26,219 reviews.

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.

Don’t miss out on dining at Nero 9, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Ristorante la Brisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Milan this evening.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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

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Day 4

Day 4 – Milan

  • Milan
  • More

Drive 8 km, 1 hour 6 min

  • Santa Maria delle Grazie
  • Pinacoteca di Brera
  • Sforzesco Castle
  • Sempione Park
  • Arco della Pace
  • More

Day 4 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.

Make Santa Maria Delle Grazie Church one of your first sightseeing stops in Milan. Rated an average of 4.5 out of 5 stars by 13,490 travelers, a visit to this local attraction makes for a great introduction to the area.

Pinacoteca Di Brera is a worthwhile attraction you can visit next. This art museum is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 26,077 reviews. Up to 417 travelers visit this site every year to make their time in Milan special.

Today is also the perfect opportunity to drop by Sforzesco Castle Art Library. This library has been rated an average of 4.6 out of 5 stars by 68,714 visitors.

If you’re keen to explore more, head to Parco Sempione. A trip to this popular park is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 72,914 previous visitors.

Another top place to visit is Arch Of Peace. This monument enjoys an average rating of 4.6 out of 5 stars from 27,502 local and international 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.

Make sure to reserve a table at Vento di Sardegna, 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 Palazzo Parigi Hotel & Grand Spa Milano, 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 Galleria Restaurant, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Bhangrabar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Rufus Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Ostello Bello Grande ensures a night out tailored to your taste.

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.

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Day 5

Day 5 – Milan, Genoa, and Pisa

  • Pisa
  • Milan
  • Genoa
  • More

Drive 322 km, 4 hours 15 min

  • Leonardo da Vinci Museum of Science and Technology
  • The City of Children and Young
  • Aquarium of Genoa
  • More

On day 5 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan, and Genoa. The day's journey will conclude in Pisa, 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.

When you're ready to see some sights, Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is a great place to start. This technology museum is rated an average of 4.5 out of 5 stars by 22,235 visitors. Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" attracts more than 532,084 visitors every year.

After soaking in Milan’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Genoa. Expect your car journey to take a minimum of 1 hour 53 min. When you arrive in Genoa, it's time to take a break from the road.

Journey into the unknown at The City Of Children And Young, a unique attraction awaiting your visit. This remarkable museum has an average rating of 4.2 out of 5 stars from 1,804 reviews.

When you’re ready to continue your sightseeing, Aquarium Of Genoa is a recommended place to visit. This public aquarium is rated an average of 4.5 out of 5 stars in 62,259 reviews. Based on recent data, the attraction hosts 1,200,000 visitors per year.

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

Don’t miss out on dining at Ristorante Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider Baribaldi Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Restaurant -Pizzeria Il Mio Capriccio. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Pisa this evening.

To truly maximize your evening out, consider visiting Jeffer Cocktails & Friends after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Le Parisien Wine Bar, another bar with an inviting ambiance. Similarly, Las Volta Cocktailbar 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 luxury holiday in Italy has plenty more in store for you.

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Day 6

Day 6 – Pisa, and Siena

  • Siena
  • Pisa
  • More

Drive 129 km, 2 hours 9 min

  • Piazza dei Cavalieri
  • Leaning Tower of Pisa
  • Angelo Caduto
  • Piazza del Duomo
  • Cattedrale di Pisa
  • More

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

Make Knights' Square one of your first sightseeing stops in Pisa. Rated an average of 4.5 out of 5 stars by 9,051 travelers, a visit to this local attraction makes for a great introduction to the area.

Leaning Tower Of Pisa is a worthwhile attraction you can visit next. This bell tower is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 116,882 reviews. Up to 3,200,000 travelers visit this site every year to make their time in Pisa special.

Today is also the perfect opportunity to drop by Angelo Caduto. This sightseeing destination has been rated an average of 4.5 out of 5 stars by 150 visitors.

If you’re keen to explore more, head to Piazza Del Duomo, Pisa. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 104,550 previous visitors.

Another top place to visit is Pisa Cathedral. This cathedral enjoys an average rating of 4.8 out of 5 stars from 8,361 local and international travelers.

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

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

Make sure to book a table at Antica Trattoria Papei, a popular restaurant in Siena. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Siena at Osteria Quattro Venti, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is Osteria da Divo. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Siena tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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.

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Day 7

Day 7 – Siena, Vatican City, and Rome

  • Rome
  • More

Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
  • More

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

Vatican City’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 2 hours 40 min. Vatican City welcomes you with a multitude of unique vacation experiences.

Take the opportunity to see Sistine Chapel. This attraction has an average rating of 4.7 out of 5 stars from 52,083 visitors.

St. Peter's Basilica is another sightseeing hotspot in the area. This major basilica has been rated an average of 4.8 out of 5 stars by 131,043 travelers. Up to 11,000,000 people visit St. Peter's Basilica every year.

Vatican City is also the home of Saint Peter's Square. Around 38,954 people have rated this square an average of 4.8 out of 5 stars.

Another place you’ll want to visit is Vatican Museums, which hosts up to 1,612,530 visitors every year. With an average rating of 4.6 out of 5 stars from a total of 133,310 reviews, a visit to this art museum is a great idea.

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 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.

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 your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Sant' Eustachio Caffè is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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

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Day 8

Day 8 – Rome

  • Rome
  • More

Drive 5 km, 52 min

  • Castel Sant'Angelo
  • Campo de' Fiori
  • Piazza Navona
  • Pantheon
  • Largo di Torre Argentina
  • More

Day 8 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 4 nights nights remaining.

Kick off the day at Castel Sant'angelo, a top pick for today’s sightseeing. Attracting approximately 918,591 visits every year, this attraction is a must-see. This museum is rated an average of 4.7 out of 5 stars in 72,431 reviews.

Today is also your chance to visit Campo De' Fiori. Campo De' Fiori is a square with an average rating of 4.4 out of 5 stars from 51,133 reviews.

Piazza Navona is another top attraction we highly recommend you visit today. This square is rated an average of 4.7 out of 5 stars by 158,771 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Pantheon. This roman temple is rated an average of 4.8 out of 5 stars by 189,682 visitors. Visiting Pantheon means you'll be one of 30,000,000 people who do so every year.

Lastly, don’t miss out on Largo Di Torre Argentina, a famous square in Rome. This attraction is rated an average of 4.5 out of 5 stars by 30,433 travelers.

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.

Treat yourself to a wonderful meal at DEROMA - Farine Romane, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at Centro. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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.

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Day 9

Day 9 – Rome

  • Rome
  • More

Drive 15 km, 1 hour 7 min

  • Basilica di San Giovanni in Laterano
  • Basilica Papale di Santa Maria Maggiore
  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • More

Day 9 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.

Start your sightseeing with a visit to Archbasilica Of St. John Lateran. This catholic cathedral is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.8 out of 5 stars by 21,370 visitors.

Basilica Di Santa Maria Maggiore is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 27,678 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Trevi Fountain. Visitors have rated this sculpture an average of 4.8 out of 5 stars in 343,494 reviews.

Piazza Di Spagna is another unique site you can experience today. This attraction is a square rated an average of 4.7 out of 5 stars in 113,658 reviews.

Make your way to the fantastic Spanish Steps, perhaps the most famous monumental staircase in Rome. This attraction is rated 4.5 out of 5 stars by 57,211 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.

Treat yourself to a delightful dinner at Ristorante Tema, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Maccheroni? It's another excellent option with a diverse menu. Consider reserving a table at RoYaL Art Cafè Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

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Day 10

Day 10 – Rome

  • Rome
  • More

Drive 12 km, 55 min

  • Villa Borghese
  • Passeggiata del Pincio
  • Piazza del Popolo
  • Circus Maximus
  • Giardino degli Aranci
  • More

Day 10 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.

Be one of the day’s first visitors at Villa Borghese. This urban zone of rome is rated an average of 4.6 out of 5 stars by 69,749 visitors.

When you’re finished at Villa Borghese, head to Passeggiata Del Pincio. This one-of-a-kind park is rated an average of 4.7 out of 5 stars in 11,134 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza Del Popolo. This square is rated an average of 4.6 out of 5 stars by 89,807 visitors.

If you’re keen to explore more, then consider a visit to Circus Maximus. This circus is a much-appreciated attraction with an average rating of 4.4 out of 5 stars from 44,741 visitors.

To round off your sightseeing experience, make your way to Orange Garden. This famous park is rated an average of 4.7 out of 5 stars by 17,939 travelers.

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.

Savor the flavors at Harry's Bar, a top pick for dinner tonight. Alternatively, Ristorante Amedeo beckons with its unique menu offerings. Also, consider VinAllegro. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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

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Day 11

Day 11 – Rome

  • Rome
  • More

Drive 3 km, 42 min

  • Colosseum
  • Roman Forum
  • Campidoglio
  • Capitoline Museums
  • Altar of the Fatherland
  • More

Day 11 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.

Your sightseeing of the day begins at Colosseum, a remarkable roman amphitheatre where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 328,821 reviews. Each year, this popular place of interest welcomes approximately 7,400,000 visitors.

Next, satisfy your wanderlust at Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 travelers.

Capitoline Hill is another must-visit attraction. This renowned hill offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 19,557 travelers, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Capitoline Museums. This well-loved art museum boasts a 4.7 out of 5-star rating from 13,142 reviews. In a single year, approximately 452,232 visitors add this sightseeing spot to their travel itineraries.

When there’s still energy left for exploring, Altare Della Patria awaits. If you’ve been interested in experiencing an architectural structure, this is a top pick rated 4.8 out of 5 stars by 49,843 previous visitors. Each year, approximately 1,683,070 people travel to Rome to experience it.

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

Dine in style at Cantina e Cucina, a top recommendation for dinner tonight. Or, for a change of pace, Bono Bottega Nostrana - Piazza Di Spagna boasts a menu that's sure to impress. Also, be sure to check out Ai Tre Scalini. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

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Day 12

Day 12 – Rome, Arezzo, and Florence

  • Florence
  • Arezzo
  • More

Drive 302 km, 3 hours 51 min

  • Basilica di San Francesco
  • Santa Maria della Pieve
  • Piazza Grande
  • More

On day 12 of your luxury holiday in Italy, your road trip route will take you exploring the best of Arezzo. The day's journey will conclude in Florence, 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.

When you’re ready to jump back into the car and say goodbye to Rome, you’ll hit the road in the direction of Arezzo. This drive usually takes around 2 hours 37 min. When you arrive, enjoy some sightseeing.

Drop by the renowned San Francesco, Arezzo. This popular minor basilica has been rated an average of 4.6 out of 5 stars by 2,377 visitors. Based on recent data, this attraction is visited by more than 20,939 travelers every year.

Another unforgettable place to experience is Santa Maria Della Pieve. Rated 4.8 out of 5 stars by 720 visitors, this church building deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Piazza Grande. This square has been rated an average of 4.6 out of 5 stars in 14,465 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. 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 Florence for you so you can browse their menus in advance and make a reservation.

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative, and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary, and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary, and international foodies seeking culinary excellence.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing 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.

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Day 13

Day 13 – Florence

  • Florence
  • More

Drive 6 km, 45 min

  • Piazza della Signoria
  • Palazzo Vecchio
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazzale Michelangelo
  • More

Day 13 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.

Begin your sightseeing with a visit to Piazza Della Signoria. This extraordinary square is rated an average of 4.8 out of 5 stars by 66,956 visitors.

Next, make your way to Palazzo Vecchio. This top attraction is a palazzo with an average rating of 4.7 out of 5 stars by 19,049 visitors.

We also recommend a visit to Uffizi Gallery. Hosting 2,011,219 visitors every year, Uffizi Gallery is one of the most popular places to visit in Florence. This national museum is rated 4.7 out of 5 stars by 61,794 travelers.

If you’re keen to keep exploring, visit Ponte Vecchio. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 118,099 travelers.

Today is also your chance to spend some time at Piazzale Michelangelo. This square is rated an average of 4.8 out of 5 stars by 77,744 travelers.

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

Make sure to reserve a table at Trattoria Da Burde, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Buca Mario, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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Day 14

Day 14 – Florence, and Bologna

  • Bologna
  • Florence
  • More

Drive 105 km, 1 hour 54 min

  • Cathedral of Santa Maria del Fiore
  • Accademia Gallery
  • Basilica of Santa Maria Novella
  • More

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

An excellent attraction to start your day with is Cathedral Of Santa Maria Del Fiore. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Continue your journey at Galleria Dell'accademia. This national museum is rated 4.6 out of 5 stars by 34,429 travelers from near and far. Approximately 1,719,645 people come to this place of interest every year to enjoy a unique experience in Florence.

Florence is also the home of Central Market. This point of interest has an average rating of 4.4 out of 5 stars from 43,100 visitors.

You can continue your self-guided sightseeing tour at Basilica Di Santa Maria Novella, Firenze (fi). Rated 4.7 out of 5 stars by 23,075 visitors, a visit to this top sight is time well spent.

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.

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

Have a memorable dining experience in Bologna by booking a table at I Portici, renowned as a 1-star Michelin restaurant presenting an exceptional creative, and contemporary menu. For a different culinary experience in Bologna, Ahimè shines as one of the top destinations, known for its delicious country cooking cuisine. This Bib Gourmand-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, Trattoria di Via Serra is known as a top local spot for its delicious emilian cuisine in Bologna. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

If you’re not ready to end the night just yet, Bar Senza Nome offers a perfect venue to relax and savor a drink. Similarly, Bar Maurizio is well-suited for those looking to unwind in a social setting. Brewdog Bar Bologna 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!

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Day 15

Day 15 – Bologna - departure day

  • Bologna - Departure day
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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 Bologna before saying goodbye.

Maximize your last day in Italy and go on a shopping spree in Bologna’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Portici Di Bologna. This extraordinary sightseeing destination and attraction is rated an average of 4.8 out of 5 stars in 101 reviews, and is an excellent choice for your last sightseeing in Bologna.

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

You will then say farewell to Bologna 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!

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