Luxury 6-Day Italy Road Trip from Rome traveling west to Siena, Florence, and Perugia

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Escape for the holiday of a lifetime with this 6-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 Rome, 1 night in Siena, 1 night 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 6-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 6-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 6-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, Pisa, Florence, 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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  • Trevi Fountain
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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 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Your sightseeing of the day begins at Trevi Fountain, a remarkable sculpture where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 343,494 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 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.

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

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Sant' Eustachio Caffè is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise a toast to the start of your 6-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Rome, and Siena

  • Siena
  • Rome
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Drive 243 km, 3 hours 29 min

  • Roman Forum
  • Colosseum
  • Pantheon
  • Piazza di Spagna
  • Piazza del Popolo
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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 Rome. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Journey into the unknown at Roman Forum, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.7 out of 5 stars from 114,450 reviews.

When you’re ready to continue your sightseeing, Colosseum is a recommended place to visit. This roman amphitheatre is rated an average of 4.7 out of 5 stars in 328,821 reviews. Based on recent data, the attraction hosts 7,400,000 visitors per year.

Another must-see attraction in Rome is Pantheon. This spectacular roman temple gets over 30,000,000 visitors every year. Rated an average of 4.8 out of 5 stars by 189,682 travelers, this popular tourist destination in Rome offers an experience you will remember.

Piazza Di Spagna is another popular stop on travelers' itineraries in Rome. This square promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 113,658 reviews.

Lastly, don't miss out on Piazza Del Popolo. Rated 4.6 out of 5 stars by 89,807 local and international travelers, it's a popular place to visit.

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.

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

Savor the flavors at Antica Trattoria Papei, a top pick for dinner tonight. Alternatively, Osteria Quattro Venti beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Maudit Pub is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Impero Siena 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 3

Day 3 – Siena, Pisa, and Florence

  • Florence
  • Siena
  • Pisa
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Drive 222 km, 3 hours 31 min

  • Piazza del Campo
  • Duomo di Siena
  • Giardino Scotto
  • Piazza del Duomo
  • Leaning Tower of Pisa
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On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Siena, and Pisa. The day's journey will conclude in Florence, 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.

An excellent attraction to start your day with is Piazza Del Campo. This square is rated an average of 4.8 out of 5 stars in 64,175 reviews.

Continue your journey at Siena Cathedral. This domus is rated 4.8 out of 5 stars by 21,656 travelers from near and far.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 43 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Kick off the day at Cittadella Nuova, a top pick for today’s sightseeing. This fortress is rated an average of 4.4 out of 5 stars in 3,114 reviews.

Today is also your chance to visit Piazza Del Duomo, Pisa. Piazza Del Duomo, Pisa is a square with an average rating of 4.7 out of 5 stars from 104,550 reviews.

Leaning Tower Of Pisa is another top attraction we highly recommend you visit today. This bell tower is rated an average of 4.7 out of 5 stars by 116,882 visitors. In a single year, this bell tower hosts approximately 3,200,000 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 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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative, and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary, and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary, and international cuisine lovers seeking top-notch culinary experiences.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 4

Day 4 – Florence, and Perugia

  • Perugia
  • Florence
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Drive 154 km, 2 hours 36 min

  • Piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Uffizi Gallery
  • Piazzale Michelangelo
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Wake up to day 4 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 Perugia, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

Make Piazza Della Signoria your first stop of the day. Previous visitors have rated this square an average of 4.8 out of 5 stars in 66,956 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.

Ponte Vecchio is another attraction you can visit on this day of your vacation. This deck arch bridge has an average rating of 4.7 out of 5 stars by 118,099 visitors.

When you’re finished at Ponte Vecchio, the perfect next stop is Uffizi Gallery. This national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. Uffizi Gallery attracts approximately 2,011,219 visitors annually.

If you’re keen to explore even more, then consider a visit to Piazzale Michelangelo. This square is a top place to visit, with a rating of 4.8 out of 5 stars from 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 day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Perugia. Savor the local cuisine and relax as you recount the day's experiences.

Treat yourself to a delightful dinner at Ristorante Settimo Sigillo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bar Pellas? It's another excellent option with a diverse menu. Consider reserving a table at La Taverna as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

To truly maximize your evening out, consider visiting Tommi Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Valentina, another bar with an inviting ambiance. Similarly, Caffe Dal Perugino 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 5

Day 5 – 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
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Wake up to day 5 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.

As you’ve unraveled the marvels of Perugia, it’s time to gear up for the next part of your road trip adventure. Set course for Vatican City! Under favorable conditions, your drive to Vatican City may take around 2 hours 17 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Seize the day by visiting some of the best attractions in the area, like Vatican Museums. This extraordinary art museum has an average rating of 4.6 out of 5 stars from 133,310 visitors. Each year, around 1,612,530 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Saint Peter's Square. This square is rated an average of 4.8 out of 5 stars in 38,954 reviews.

While in Vatican City, we also recommend a visit to Sistine Chapel. This chapel has been rated an average of 4.7 out of 5 stars in 52,083 reviews.

If you’re keen to explore even more, then consider a visit to St. Peter's Basilica. This attraction gets around 11,000,000 yearly visitors. With an average rating of 4.8 out of 5 stars by 131,043 travelers, this major basilica is a highly recommended stop on your sightseeing around Vatican City.

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.

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.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

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

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Day 6

Day 6 – Rome - departure day

  • Rome - Departure day
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  • Piazza Navona
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Today is the last day of your 6-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.

Make the most of your final day in Italy by visiting Rome’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Piazza Navona. This extraordinary square and attraction is rated an average of 4.7 out of 5 stars in 158,771 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.

If you're in the mood to try something new, consider Maccheroni, another top spot with a mouthwatering 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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