Luxury 9-Day Italy Road Trip from Rimini to Venice, Florence, Rome, and Ancona and surrounding area

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Experience travel that redefines comfort and elegance with this 9-day luxury road trip in Italy. Witness Italy's awe-inspiring scenery, delight in the finest culinary offerings, and enjoy the ultimate comfort in top-tier accommodations.

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 Rimini, 2 nights in Venice, 1 night in Florence, 1 night in Rome, and 2 nights in Ancona, 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 9-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 9-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 9-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 Rimini, Viserbella, Venice, Lido, Florence, Rome, Loreto, Sirolo, Ancona, Serra San Quirico, Fabriano, and Senigallia 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 – Rimini - arrival day

  • Rimini - Arrival day
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  • Arco di Augusto
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Your luxury holiday in Italy begins as soon as you reach the city of Rimini, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

When you’re ready for some sightseeing, make your way to Arch Of Augustus. This much-appreciated triumphal arch is rated 4.6 out of 5 stars in 12,375 reviews.

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

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

Enjoy a delicious meal at Bar Lento, a highly-rated dining destination in Rimini. If you're eager to try something different, consider Ristorante Lo Zodiaco Rimini, another top spot with a tantalizing menu. You might also want to secure a reservation at Amarina. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Rimini this evening.

If you’re not ready to end the night just yet, Caffè Il Borgo offers a perfect venue to relax and savor a drink. Similarly, Primo Bacio Città Lounge Bar is well-suited for those looking to unwind in a social setting. Hobo's is another excellent spot to enjoy a nightcap after a delightful meal.

Raise a toast to the start of your 9-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Rimini, Viserbella, and Venice

  • Venice
  • Rimini
  • Viserbella
  • More

Drive 266 km, 3 hours 7 min

  • Parco Federico Fellini
  • Fountain of the four horses
  • Italia in Miniatura
  • More

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

When you're ready to see some sights, Parco Federico Fellini is a great place to start. This park is rated an average of 4.5 out of 5 stars by 11,076 visitors.

Another popular attraction you can visit today is Fountain Of The Four Horses. This park has an average rating of 4.6 out of 5 stars from 2,798 travelers.

After soaking in Rimini’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Viserbella. Expect your car journey to take a minimum of 14 min. When you arrive in Viserbella, it's time to take a break from the road.

Begin your sightseeing with a visit to Italia In Miniatura. This miniature park is rated an average of 4.4 out of 5 stars in 20,510 reviews.

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

Set out on a gastronomic journey in Venice by reserving a table at Local. Renowned for its 1-star Michelin recognition, this restaurant presents an outstanding menu of contemporary cuisine. For a different taste, head over to Wistèria, renowned for its delectable contemporary, and venetian dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Quadri, a highly rated local gem known for its exquisite modern 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 Venice.

Keep the excitement of the evening going by visiting a bar or two. Al Parlamento is an excellent place to start. You could also check out Adagio, offering a different kind of charm. A last recommendation for the day is Il Mercante. 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 stress-free luxury holiday in Italy has plenty more in store for you.

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Day 3

Day 3 – Venice, and Lido

  • Venice
  • Lido
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Drive 4 km, 1 hour

  • St. Mark's Square
  • Saint Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • Giardini della Biennale
  • More

Day 3 of your luxury road trip in Italy begins and concludes in the city of Venice. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Venice, where you still have 1 night nights remaining.

When you're ready to see some sights, Piazza San Marco is a great place to start. This square is rated an average of 4.7 out of 5 stars by 152,982 visitors.

Another popular attraction you can visit today is St Mark's Basilica. This cathedral has an average rating of 4.7 out of 5 stars from 18,439 travelers.

We also recommend a stop at Doge's Palace. This site gets more than 318,104 visitors annually. The palace has been rated an average of 4.7 out of 5 stars by 24,775 visitors.

If you're keen to explore more, consider visiting Bridge Of Sighs. This footbridge is a popular attraction with an average rating of 4.6 out of 5 stars from 18,223 reviews.

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

Savor the flavors at Cantina Do Spade, a top pick for dinner tonight. Alternatively, Trattoria Al Gazzettino beckons with its unique menu offerings. Also, consider Trattoria Bar Pontini. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Irish Pub Venezia, a well-loved spot among locals and tourists. Or, head to Dolce Vita Venezia. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Devils Forest Pub, another top-rated place in the area.

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 4

Day 4 – Venice, and Florence

  • Florence
  • Venice
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Drive 262 km, 3 hours 26 min

  • Grand Canal
  • Rialto Bridge
  • Palazzo Contarini del Bovolo
  • Teatro La Fenice
  • Peggy Guggenheim Collection
  • More

Wake up to day 4 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Venice. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Begin your sightseeing with a visit to Grand Canal. This extraordinary point of interest is rated an average of 4.8 out of 5 stars by 3,806 visitors.

Next, make your way to Rialto Bridge. This top attraction is a stone bridge with an average rating of 4.7 out of 5 stars by 141,666 visitors.

We also recommend a visit to Palazzo Contarini Del Bovolo. This sightseeing destination is rated 4.5 out of 5 stars by 11,745 travelers.

If you’re keen to keep exploring, visit Teatro La Fenice. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 10,677 travelers.

Today is also your chance to spend some time at Peggy Guggenheim Collection. This art museum is rated an average of 4.6 out of 5 stars by 10,128 travelers. It’s estimated that 92,922 people visit this fantastic attraction every year.

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 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.

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 dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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 5

Day 5 – Florence, Vatican City, and Rome

  • Rome
  • Florence
  • More

Drive 284 km, 4 hours 1 min

  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Piazzale Michelangelo
  • St Peter's Basilica
  • More

On day 5 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence, and Vatican City. The day's journey will conclude in Rome, 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 for some sightseeing, make your way to Cathedral Of Santa Maria Del Fiore. This much-appreciated church is rated 4.8 out of 5 stars in 76,359 reviews.

Next up is Ponte Vecchio. This deck arch bridge has an average rating of 4.7 out of 5 stars from 118,099 visitors.

Another top sightseeing recommendation is Piazzale Michelangelo. This square has been rated 4.8 out of 5 stars in 77,744 reviews.

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 3 hours 9 min, without any stops or traffic disruptions.

Kick off the day at St. Peter's Basilica, a top pick for today’s sightseeing. Attracting approximately 11,000,000 visits every year, this attraction is a must-see. This major basilica is rated an average of 4.8 out of 5 stars in 131,043 reviews.

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.

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean, and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative, and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean, and creative menu.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Sant' Eustachio Caffè offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

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

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Day 6

Day 6 – Rome, Loreto, Sirolo, and Ancona

  • Ancona
  • Loreto
  • Sirolo
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Drive 316 km, 4 hours 46 min

  • Sanctuary of the Holy House of Loreto
  • 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 Ancona, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Loreto, and Sirolo.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Loreto. 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 25 min. Upon reaching Loreto, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Begin your sightseeing with a visit to Sanctuary Of The Holy House Of Loreto. This church is rated an average of 4.8 out of 5 stars in 19,100 reviews.

When you’ve had your share of Loreto, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Sirolo. Your travel time is around 18 min.

Start your sightseeing with a visit to Spiaggia Del Frate - Sottosanta. This point of interest is rated an average of 4.4 out of 5 stars from 3,137 visitors.

Splendide Terrazze Del Conero is another popular attraction you could visit today. This point of interest has a rating of 4.8 out of 5 stars from 1,225 visitors.

Parco Della Repubblica is also highly recommended by travelers. This park has a rating of 4.5 out of 5 stars from 976 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Ancona. 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 Ancona so you can check out the menus and make advance reservations.

Start your culinary exploration in Ancona by securing a reservation at Sot'Ajarchi. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of seafood, and from the marches cuisine. Immerse yourself in the culinary delights of Zucchero a Velò, a popular restaurant in Ancona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

Let the evening flow smoothly from dinner to drinks at Posa Bar, a top-rated bar in the area. For other recommendations, Bar Four Roses provides a perfect setting for rounding out your night with style and great drinks. Likewise, Amarillo Beer Bar Ancona 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!

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Day 7

Day 7 – Ancona, Sirolo, San Germano, Serra San Quirico, San Vittore, and Fabriano

  • Ancona
  • Sirolo
  • Serra San Quirico
  • Fabriano
  • More

Drive 193 km, 3 hours 21 min

  • Beach of the Two Sisters
  • Parco Naturale Regionale Gola della Rossa e di Frasassi
  • Frasassi Caves
  • Paper and Watermark Museum Fabriano
  • More

Day 7 of your luxury road trip in Italy is another opportunity to explore what this region has to offer. Start your day with a drive to visit the amazing attractions in the surrounding area of Ancona. After a day of sightseeing, return to the city, where you still have 1 night left to enjoy. End your evening with a fulfilling dinner at one of the finest restaurants in Ancona, savoring the local culinary delights.

Set your GPS to Sirolo and hit the road. Expect a journey of approximately 31 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Sirolo beckons with new experiences!

Start your sightseeing with a visit to Beach Of The Two Sisters. This sightseeing destination is a popular stop on travelers’ itineraries in Sirolo, with an average rating of 4.6 out of 5 stars by 2,406 visitors.

When you’ve had your share of Sirolo, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of San Germano. Your travel time is around 18 min.

Begin your sightseeing with a visit to Grotte Nel Sottosuolo Di Camerano - Biglietteria. This sightseeing destination is rated an average of 4.6 out of 5 stars in 1,983 reviews.

Set your GPS to Serra San Quirico and hit the road. Expect a journey of approximately 48 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Serra San Quirico beckons with new experiences!

Be one of the day’s first visitors at Parco Naturale Regionale Gola Della Rossa E Di Frasassi. This park is rated an average of 4.6 out of 5 stars by 3,515 visitors.

When you’re done exploring the best attractions, you’ll drive back to your luxury accommodation near the city of Ancona.

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

Dine in style at Amarcord, a top recommendation for dinner tonight. Or, for a change of pace, Bontà delle Marche boasts a menu that's sure to impress. Also, be sure to check out Donegal Irish Pub. Known as a local hotspot, it’s a great choice for tonight in Ancona.

Continue the enjoyment post-dinner at Alla Tazza D'oro, a cherished local gathering spot renowned for its welcoming atmosphere.

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

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Day 8

Day 8 – Ancona, Senigallia, and Rimini

  • Rimini
  • Ancona
  • Senigallia
  • More

Drive 112 km, 2 hours 16 min

  • Piazza del Plebiscito
  • Cattedrale di San Ciriaco
  • Passetto
  • Mole Vanvitelliana
  • Rocca Roveresca
  • More

Wake up to day 8 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Ancona, and Senigallia. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Drop by the renowned Piazza Del Plebiscito. This popular square has been rated an average of 4.4 out of 5 stars by 2,631 visitors.

Another unforgettable place to experience is Cathedral Basilica Of St. Cyriacus. Rated 4.6 out of 5 stars by 2,724 visitors, this cathedral deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Passetto. This sightseeing destination has been rated an average of 4.5 out of 5 stars in 2,797 reviews.

Another favorite attraction in the area is Lazzaretto Of Ancona. This building and popular place of interest enjoys a rating of 4.4 out of 5 stars from 4,023 local and international travelers.

Fasten your seatbelt and make your way to your next stop. Senigallia, 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 Ancona to Senigallia may take around 38 min without traffic disruptions. Upon arrival in Senigallia, we highly recommend checking out some of the top attractions.

Journey into the unknown at Rocca Roveresca, a unique attraction awaiting your visit. This remarkable point of interest has an average rating of 4.5 out of 5 stars from 5,207 reviews.

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

Discover a world of culinary delights in Rimini, 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.

Dive into a culinary adventure like no other in Rimini by booking a table at Guido. This popular restaurant holds 1 Michelin star and offers an exceptional menu of seafood, and modern cuisine. For another culinary dining option, venture to Abocar Due Cucine, celebrated for its delectable creative, and international menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Osteria de Börg, a top local restaurant known for its tantalizing from romagna, and traditional menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

After savoring a delicious meal, step into the vibrant nightlife at Bar Capogiro, where the evening is just getting started. In the same way, Caffè Cavour offers a unique charm perfect for experiencing the local bar scene in Rimini. Bar Ilde - Il Baretto Della Buona Piadina is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day 9

Day 9 – Rimini - departure day

  • Rimini - Departure day
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  • Cavour Square
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Today is the last day of your 9-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 Rimini before saying goodbye.

Maximize your last day in Italy and go on a shopping spree in Rimini’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 Piazza Cavour. This extraordinary sightseeing destination and attraction is rated an average of 4.5 out of 5 stars in 11,447 reviews, and is an excellent choice for your last sightseeing in Rimini.

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

Dine in style at Sabbioni Pizza & Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, In The Courtyard Center Gourmet Pizza boasts a menu that's sure to impress.

You will then say farewell to Rimini 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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