Luxury 6-Day Italy Road Trip from Perugia to Florence, Siena, and Rome and surrounding area

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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 Perugia, 1 night in Florence, 1 night in Siena, and 1 night in Rome, 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 Perugia, Pissignano, Magione, Florence, Pisa, Siena, and Rome 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 – Perugia - arrival day

  • Perugia - Arrival day
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  • Piazza IV Novembre
  • More

Your luxury holiday in Italy begins as soon as you reach the city of Perugia. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Drop by the renowned Piazza Iv Novembre. This popular square has been rated an average of 4.6 out of 5 stars by 9,189 visitors.

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

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

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

After savoring a delicious meal, step into the vibrant nightlife at Tommi Bar, where the evening is just getting started. In the same way, Valentina offers a unique charm perfect for experiencing the local bar scene in Perugia. Caffe Dal Perugino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 – Perugia, Pissignano, Magione, and Florence

  • Florence
  • Perugia
  • Pissignano
  • Magione
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Drive 261 km, 4 hours 25 min

  • Carducci Gardens
  • Porta Marzia
  • Rocca Paolina
  • Fonti del Clitunno
  • Parco Regionale del Lago Trasimeno
  • 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 Florence, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Perugia, Pissignano, and Magione.

Journey into the unknown at Carducci Gardens, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.5 out of 5 stars from 1,768 reviews.

When you’re ready to continue your sightseeing, Porta Marzia is a recommended place to visit. This city gate is rated an average of 4.6 out of 5 stars in 119 reviews.

Another must-see attraction in Perugia is Rocca Paolina. Rated an average of 4.7 out of 5 stars by 7,128 travelers, this popular tourist destination in Perugia offers an experience you will remember.

After soaking in Perugia’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pissignano. Expect your car journey to take a minimum of 42 min. When you arrive in Pissignano, it's time to take a break from the road.

Make Clitumnus your first stop of the day. Previous visitors have rated this roman deity an average of 4.3 out of 5 stars in 6,692 reviews.

Set your GPS to Magione and hit the road. Expect a journey of approximately 1 hour 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Magione beckons with new experiences!

Begin your sightseeing with a visit to Parco Regionale Del Lago Trasimeno. This extraordinary park is rated an average of 4.4 out of 5 stars by 8,831 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.

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

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.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence, and Pisa. The day's journey will conclude in Siena, 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.

Drop by the renowned Piazza Della Signoria. This popular square has been rated an average of 4.8 out of 5 stars by 66,956 visitors.

Another unforgettable place to experience is Ponte Vecchio. Rated 4.7 out of 5 stars by 118,099 visitors, this deck arch bridge deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Piazzale Michelangelo. This square has been rated an average of 4.8 out of 5 stars in 77,744 reviews.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 19 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Your sightseeing of the day begins at Leaning Tower Of Pisa, a remarkable bell tower where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 116,882 reviews. Each year, this popular place of interest welcomes approximately 3,200,000 visitors.

Next, satisfy your wanderlust at Piazza Del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 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.

Discover a world of culinary delights in Siena, 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 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.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 4

Day 4 – Siena, Vatican City, and Rome

  • Rome
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Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
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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 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 Siena, 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 40 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make Sistine Chapel your first stop of the day. Previous visitors have rated this chapel an average of 4.7 out of 5 stars in 52,083 reviews.

Next up, make a stop at St. Peter's Basilica. With an average rating of 4.8 out of 5 stars by 131,043 visitors, it's easy to understand why so many people visit this major basilica every year. In fact, this attraction welcomes 11,000,000 annual visitors.

Saint Peter's Square is another attraction you can visit on this day of your vacation. This square has an average rating of 4.8 out of 5 stars by 38,954 visitors.

When you’re finished at Saint Peter's Square, the perfect next stop is Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars in 133,310 reviews. Vatican Museums attracts approximately 1,612,530 visitors annually.

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.

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.

Let the evening flow smoothly from dinner to drinks at La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Sant' Eustachio Caffè provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino 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 stress-free luxury holiday in Italy has plenty more in store for you.

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Day 5

Day 5 – Rome, and Perugia

  • Perugia
  • Rome
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Drive 177 km, 3 hours 15 min

  • Roman Forum
  • Colosseum
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
  • More

Wake up to day 5 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 Rome.

When you're ready to see some sights, Roman Forum is a great place to start. This square is rated an average of 4.7 out of 5 stars by 114,450 visitors.

Another popular attraction you can visit today is Colosseum. This roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 travelers. Every year, 7,400,000 travelers come to experience this site to make the most of their time in Rome.

We also recommend a stop at Trevi Fountain. The sculpture has been rated an average of 4.8 out of 5 stars by 343,494 visitors.

If you're keen to explore more, consider visiting Pantheon. This roman temple is a popular attraction with an average rating of 4.8 out of 5 stars from 189,682 reviews. As a top-rated attraction, it's no surprise that 30,000,000 people visit Pantheon every year.

Piazza Navona is another easily accessible place to visit on this day of your trip. Stop by this square, rated 4.7 out of 5 stars in 158,771 reviews, to discover more of what makes it unique.

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 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 Perugia so you can check out the menus and make advance reservations.

Treat yourself to a wonderful meal at Ristorante del Sole, a top-rated dining spot in Perugia. If you're in the mood for something new, try Al Mangiar Bene, another premier location with a delectable menu. You might also want to book a table at Elfo Pub Perugia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Perugia.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Caffè Fortebraccio, known for its inviting atmosphere. Caffe Del Banco is another great option if you’re looking for a place to get the night started. Similarly, Dempsey's Perugia 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 6

Day 6 – Perugia - departure day

  • Perugia - Departure day
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  • Etruscan Arch
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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 Perugia before saying goodbye.

Make the most of your final day in Italy by visiting Perugia’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 Etruscan Arch. This extraordinary architectural element and attraction is rated an average of 4.7 out of 5 stars in 1,190 reviews, and is an excellent choice for your last sightseeing in Perugia.

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

Have a fantastic dining experience at Sangallo Palace Hotel, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria a Priori offers an enticing alternative with its varied menu.

You will then say farewell to Perugia 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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