Luxury One-Week Italy Road Trip from Rome to Siena, Florence, and Perugia

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Set off on the ultimate travel extravagance with this 8-day luxury road trip across Italy. Every aspect of your journey is crafted to provide a sophisticated and comfortable experience. Enjoy a holiday where luxury unfolds at every turn in each stop of your adventure 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 3 nights in Rome, 1 night in Siena, 2 nights in Florence, and 1 night in Perugia, 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 Rome, Siena, Bologna, Florence, Pisa, and Perugia 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 – Rome - arrival day

  • Rome - Arrival day
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  • Campo de' Fiori
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Your luxury holiday in Italy begins as soon as you reach the city of Rome, where you'll be staying for 2 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

An excellent attraction to start your day with is Campo De' Fiori. This square is rated an average of 4.4 out of 5 stars in 51,133 reviews.

Tonight, you will be treated to a stay at one of the best luxury hotels in Rome. 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 Rome for you, so you can check out the menus and make your reservation in advance.

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

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.

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 – Rome

  • Rome
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Drive 11 km, 1 hour 19 min

  • Castel Sant'Angelo
  • Piazza Navona
  • Pantheon
  • Piazza del Popolo
  • Villa Borghese
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Day 2 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 Castel Sant'angelo your first stop of the day. Previous visitors have rated this museum an average of 4.7 out of 5 stars in 72,431 reviews. More than 918,591 people visit this place of interest every year.

Next up, make a stop at Piazza Navona. With an average rating of 4.7 out of 5 stars by 158,771 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 Del Popolo. This square is rated an average of 4.6 out of 5 stars in 89,807 reviews.

If you’re keen to explore even more, then consider a visit to Villa Borghese. This urban zone of rome is a top place to visit, with a rating of 4.6 out of 5 stars from 69,749 reviews.

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.

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.

Keep the evening going at The Apartment Bar Roma, a great choice for enjoying the after-dinner hours with a drink. You could also go to Hotel Hassler Roma, which offers a similarly pleasant setting and great drinks.

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 – Rome, and Siena

  • Siena
  • Rome
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Drive 242 km, 3 hours 34 min

  • Roman Forum
  • Colosseum
  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
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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 Rome.

An excellent attraction to start your day with is Roman Forum. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Continue your journey at Colosseum. This roman amphitheatre is rated 4.7 out of 5 stars by 328,821 travelers from near and far. Approximately 7,400,000 people come to this place of interest every year to enjoy a unique experience in Rome.

Rome is also the home of Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars from 343,494 visitors.

You can continue your self-guided sightseeing tour at Piazza Di Spagna. Rated 4.7 out of 5 stars by 113,658 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Spanish Steps. With an average rating of 4.5 out of 5 stars from 57,211 reviews, it’s hard to refuse the opportunity to see this monumental staircase.

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 day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Siena. Savor the local cuisine and relax as you recount the day's experiences.

Treat yourself to a delightful dinner at Antica Trattoria Papei, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria Quattro Venti? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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, Bologna, and Florence

  • Florence
  • Siena
  • Bologna
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Drive 292 km, 4 hours 7 min

  • Piazza del Campo
  • Duomo di Siena
  • Two Towers
  • Piazza Maggiore
  • More

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Siena, and Bologna. 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 for some sightseeing, make your way to Piazza Del Campo. This much-appreciated square is rated 4.8 out of 5 stars in 64,175 reviews.

Next up is Siena Cathedral. This domus has an average rating of 4.8 out of 5 stars from 21,656 visitors.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Bologna. This drive usually takes around 2 hours 5 min. When you arrive, enjoy some sightseeing.

Start your sightseeing with a visit to Two Towers. This tower is rated an average of 4.7 out of 5 stars from 25,975 visitors.

Piazza Maggiore is another popular attraction you could visit today. This square has a rating of 4.7 out of 5 stars from 64,523 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.

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

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative, and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary, and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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.

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

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Day 5

Day 5 – Florence, and Pisa

  • Florence
  • Pisa
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Drive 174 km, 2 hours 54 min

  • Leaning Tower of Pisa
  • Piazza del Duomo
  • Cattedrale di Pisa
  • Cathedral of Santa Maria del Fiore
  • More

Day 5 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 Florence. 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 Florence, savoring the local culinary delights.

Make Central Market your first stop of the day. Previous visitors have rated this sightseeing destination an average of 4.4 out of 5 stars in 43,100 reviews.

Next up, make a stop at Cathedral Of Santa Maria Del Fiore. With an average rating of 4.8 out of 5 stars by 76,359 visitors, it's easy to understand why so many people visit this church every year.

Continue your road trip and head to your next destination, Pisa. This car ride takes around 1 hour 18 min.

Journey into the unknown at Leaning Tower Of Pisa, a unique attraction awaiting your visit. This remarkable bell tower has an average rating of 4.7 out of 5 stars from 116,882 reviews. Every year, Leaning Tower Of Pisa welcomes more than 3,200,000 curious visitors.

When you’re ready to continue your sightseeing, Piazza Del Duomo, Pisa is a recommended place to visit. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.

Another must-see attraction in Pisa is Pisa Cathedral. Rated an average of 4.8 out of 5 stars by 8,361 travelers, this popular tourist destination in Pisa offers an experience you will remember.

When you’ve completed everything you want to see and do, you will drive back to your luxury accommodation in Florence.

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

Enjoy a lovely meal at Trattoria Da Burde, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Buca Mario is another top choice with a popular menu. You could also check for a table at Eataly Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

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 6

Day 6 – Florence, and Perugia

  • Perugia
  • Florence
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Drive 154 km, 2 hours 32 min

  • Piazza della Signoria
  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • Piazzale Michelangelo
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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 Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

A top pick for your self-guided sightseeing tour today is Piazza Della Signoria. Previous visitors have rated this square an average of 4.8 out of 5 stars in 66,956 reviews.

Ponte Vecchio is a local recommendation that you also can pay a visit today. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Another attraction you won't want to miss is Uffizi Gallery. This national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. Every year, around 2,011,219 travelers visit this site to discover its unique features.

Basilica Of Santa Croce In Florence is another outstanding experience in Florence. Around 28,544 travelers have rated this church an average of 4.7 out of 5 stars.

If you long for more, Piazzale Michelangelo is not far away. This square is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.8 out of 5 stars in 77,744 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Perugia. 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 Perugia. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Bar Pellas is another top choice with a popular menu. You could also check for a table at La Taverna. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Perugia tonight.

Continue your lively evening at Tommi Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Valentina is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffe Dal Perugino 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.

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Day 7

Day 7 – Perugia, Vatican City, and Rome

  • Rome
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Drive 184 km, 3 hours

  • Vatican Museums
  • Saint Peter's Square
  • Sistine Chapel
  • St Peter's Basilica
  • 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 Rome, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Continue your road trip and head to your next destination, Vatican City, Vatican City. This car ride takes around 2 hours 17 min.

Begin your sightseeing with a visit to Vatican Museums. This extraordinary art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Each year, around 1,612,530 people visit this site to learn more about it.

Next, make your way to Saint Peter's Square. This top attraction is a square with an average rating of 4.8 out of 5 stars by 38,954 visitors.

We also recommend a visit to Sistine Chapel. This chapel is rated 4.7 out of 5 stars by 52,083 travelers.

If you’re keen to keep exploring, visit St. Peter's Basilica. This highly recommended sightseeing destination has received an average rating of 4.8 out of 5 stars from 131,043 travelers. Around 11,000,000 people come to experience this place of interest 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 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.

Dine in style at Ristorante Tema, a top recommendation for dinner tonight. Or, for a change of pace, Maccheroni boasts a menu that's sure to impress. Also, be sure to check out RoYaL Art Cafè Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

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Day 8

Day 8 – Rome - departure day

  • Rome - Departure day
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  • Altar of the Fatherland
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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 Rome before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Rome’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Make the most of what's left of your luxury vacation and head out to the stunning Altare Della Patria. This extraordinary architectural structure and attraction is rated an average of 4.8 out of 5 stars in 49,843 reviews, and is an excellent choice for your last sightseeing in Rome.

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

Treat yourself to a delightful dinner at Harry's Bar, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Amedeo? It's another excellent option with a diverse menu.

You will then say farewell to Rome 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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