Luxury One-Week Italy Road Trip from Venice traveling south to Florence, Siena, Rome, and Arezzo

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Experience travel that redefines comfort and elegance with this 8-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 Venice, 1 night in Florence, 1 night in Siena, 2 nights in Rome, and 1 night in Arezzo, 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 8-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 8-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 8-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 Venice, Florence, Pisa, Siena, Rome, Arezzo, and Bologna 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 – Venice - arrival day

  • Venice - Arrival day
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  • Teatro La Fenice
  • More

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

A top pick for your self-guided sightseeing tour today is Teatro La Fenice. Previous visitors have rated this opera house an average of 4.7 out of 5 stars in 10,677 reviews.

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

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

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

Let the evening flow smoothly from dinner to drinks at Al Parlamento, a top-rated bar in the area. For other recommendations, Adagio provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Mercante offers a memorable night with diverse drink options and excellent service.

Raise a toast to the start of your 8-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Venice, and Florence

  • Florence
  • Venice
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Drive 260 km, 3 hours 10 min

  • St. Mark's Square
  • Saint Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • 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 Venice. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Be one of the day’s first visitors at Piazza San Marco. This square is rated an average of 4.7 out of 5 stars by 152,982 visitors.

When you’re finished at Piazza San Marco, head to St Mark's Basilica. This one-of-a-kind cathedral is rated an average of 4.7 out of 5 stars in 18,439 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Doge's Palace. This palace is rated an average of 4.7 out of 5 stars by 24,775 visitors. Visiting Doge's Palace means you'll be one of 318,104 people who do so every year.

If you’re keen to explore more, then consider a visit to Bridge Of Sighs. This footbridge is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 18,223 visitors.

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 long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Florence so you can check out the menus and make advance reservations.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative, and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Palagio, a local gem known for its delightful italian contemporary cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 3

Day 3 – Florence, Pisa, and Siena

  • Siena
  • Florence
  • Pisa
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Drive 213 km, 3 hours 42 min

  • Piazza della Signoria
  • Ponte Vecchio
  • Piazzale Michelangelo
  • Leaning Tower of Pisa
  • Piazza del Duomo
  • More

Wake up to day 3 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 Florence, and Pisa.

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

Ponte Vecchio is another popular attraction you could visit today. This deck arch bridge has a rating of 4.7 out of 5 stars from 118,099 visitors.

Piazzale Michelangelo is also highly recommended by travelers. This square has a rating of 4.8 out of 5 stars from 77,744 visitors.

Continue your road trip and head to your next destination, Pisa. This car ride takes around 1 hour 19 min.

Make Leaning Tower Of Pisa your first stop of the day. Previous visitors have rated this bell tower an average of 4.7 out of 5 stars in 116,882 reviews. More than 3,200,000 people visit this place of interest every year.

Next up, make a stop at Piazza Del Duomo, Pisa. With an average rating of 4.7 out of 5 stars by 104,550 visitors, it's easy to understand why so many people visit this square every year.

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.

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

Make sure to reserve a table at Antica Trattoria Papei, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Quattro Venti, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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 – 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

On day 4 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 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.

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 2 hours 40 min, without any stops or traffic disruptions.

Kick off the day at Sistine Chapel, a top pick for today’s sightseeing. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Today is also your chance to visit St. Peter's Basilica. St. Peter's Basilica is a major basilica with an average rating of 4.8 out of 5 stars from 131,043 reviews. Attracting more than 11,000,000 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

Saint Peter's Square is another top attraction we highly recommend you visit today. This square is rated an average of 4.8 out of 5 stars by 38,954 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Visiting Vatican Museums means you'll be one of 1,612,530 people who do so every year.

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 exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Rome for you, so you can check out the menus and make your reservation in advance.

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

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.

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 – Rome

  • Rome
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Drive 9 km, 1 hour 11 min

  • Colosseum
  • Roman Forum
  • Pantheon
  • Piazza Navona
  • Castel Sant'Angelo
  • More

Day 5 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 1 night nights remaining.

Make Colosseum your first stop of the day. Previous visitors have rated this roman amphitheatre an average of 4.7 out of 5 stars in 328,821 reviews. More than 7,400,000 people visit this place of interest every year.

Next up, make a stop at Roman Forum. With an average rating of 4.7 out of 5 stars by 114,450 visitors, it's easy to understand why so many people visit this square every year.

Pantheon is another attraction you can visit on this day of your vacation. This roman temple has an average rating of 4.8 out of 5 stars by 189,682 visitors. Up to 30,000,000 travelers come to Rome every year to see Pantheon with their own eyes.

When you’re finished at Pantheon, the perfect next stop is Piazza Navona. This square is rated an average of 4.7 out of 5 stars in 158,771 reviews.

If you’re keen to explore even more, then consider a visit to Castel Sant'angelo. This museum is a top place to visit, with a rating of 4.7 out of 5 stars from 72,431 reviews. Castel Sant'angelo hosts around 918,591 visitors every year.

Discover a world of culinary delights in Rome, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Treat yourself to a delicious dinner at DEROMA - Farine Romane, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss Centro. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

After savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene 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 6

Day 6 – Rome, and Arezzo

  • Arezzo
  • Rome
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Drive 220 km, 3 hours 12 min

  • Altar of the Fatherland
  • Trevi Fountain
  • Piazza di Spagna
  • Piazza del Popolo
  • Villa Borghese
  • More

Wake up to day 6 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.

Your sightseeing of the day begins at Altare Della Patria, a remarkable architectural structure where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 49,843 reviews. Each year, this popular place of interest welcomes approximately 1,683,070 visitors.

Next, satisfy your wanderlust at Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars from 343,494 travelers.

Piazza Di Spagna is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 113,658 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 Piazza Del Popolo. This well-loved square boasts a 4.6 out of 5-star rating from 89,807 reviews.

When there’s still energy left for exploring, Villa Borghese awaits. If you’ve been interested in experiencing an urban zone of rome, this is a top pick rated 4.6 out of 5 stars by 69,749 previous visitors.

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.

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

Discover the culinary delights of Arezzo by securing a reservation at Octavin. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. Alternatively, La Clandestina beckons with its unique menu offerings.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Liquid Bar stands out as an excellent choice for a post-dinner cocktail.

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 – Arezzo, Bologna, and Venice

  • Venice
  • Bologna
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Drive 333 km, 4 hours 5 min

  • Palazzo d'Accursio
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

Wake up to day 7 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 1 night. The day's itinerary unfolds with a diverse array of experiences in Bologna.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Bologna. This drive usually takes around 2 hours 9 min. When you arrive, enjoy some sightseeing.

Be one of the day’s first visitors at Palazzo D'accursio. This palazzo is rated an average of 4.6 out of 5 stars by 969 visitors.

When you’re finished at Palazzo D'accursio, head to Piazza Maggiore. This one-of-a-kind square is rated an average of 4.7 out of 5 stars in 64,523 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Two Towers. This tower is rated an average of 4.7 out of 5 stars by 25,975 visitors.

If you’re keen to explore more, then consider a visit to Piazza Santo Stefano. This square is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 7,617 visitors.

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.

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

Dive into a culinary adventure like no other in Venice by booking a table at Local. This popular restaurant holds 1 Michelin star and offers an exceptional menu of contemporary cuisine. For another culinary dining option, venture to Wistèria, celebrated for its delectable contemporary, and venetian menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Quadri, a top local restaurant known for its tantalizing modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Continue your evening by exploring the vibrant nightlife scene at The Irish Pub Venezia, a prime destination for a thrilling night out. Also, don’t forget to check out Dolce Vita Venezia, a bar that offers unique local touches. Likewise, Devils Forest Pub provides an excellent alternative for a fun evening.

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

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Day 8

Day 8 – Venice - departure day

  • Venice - Departure day
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  • Rialto Bridge
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Today is the last day of your 8-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 Venice before saying goodbye.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

Make the most of what's left of your luxury vacation and head out to the stunning Rialto Bridge. This extraordinary stone bridge and attraction is rated an average of 4.7 out of 5 stars in 141,666 reviews, and is an excellent choice for your last sightseeing in Venice.

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

You will then say farewell to Venice 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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