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

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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 2 nights in Florence, 1 night in Perugia, 3 nights in Rome, and 1 night in Siena, 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 Florence, Perugia, Santa Maria degli Angeli, Rome, Siena, and Pisa 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 – Florence - arrival day

  • Florence - Arrival day
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Your luxury holiday in Italy begins as soon as you reach the city of Florence. 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 Central Market. This point of interest is rated an average of 4.4 out of 5 stars in 43,100 reviews.

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

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 Florence. Savor the local cuisine and relax as you recount the day's experiences.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Caffe San Firenze offers a tantalizing alternative with its diverse menu. And don’t miss Ditta Artigianale. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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 – Florence, and Perugia

  • Perugia
  • Florence
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Drive 153 km, 2 hours 13 min

  • Piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Piazza della Repubblica
  • Ponte Vecchio
  • Uffizi Gallery
  • 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 Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Your sightseeing of the day begins at Piazza Della Signoria, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Next, satisfy your wanderlust at Cathedral Of Santa Maria Del Fiore. This church has an average rating of 4.8 out of 5 stars from 76,359 travelers.

Piazza Della Repubblica is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.6 out of 5 stars by 22,356 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 Ponte Vecchio. This well-loved deck arch bridge boasts a 4.7 out of 5-star rating from 118,099 reviews.

When there’s still energy left for exploring, Uffizi Gallery awaits. If you’ve been interested in experiencing a national museum, this is a top pick rated 4.7 out of 5 stars by 61,794 previous visitors. Each year, approximately 2,011,219 people travel to Florence to experience it.

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.

Make sure to book a table at Ristorante Settimo Sigillo, a popular restaurant in Perugia. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Perugia at Bar Pellas, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is La Taverna. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Perugia tonight.

Unwind after your meal by stepping into Tommi Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Valentina offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffe Dal Perugino, 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 – Perugia, Santa Maria degli Angeli, and Rome

  • Rome
  • Assisi
  • Santa Maria degli Angeli
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Drive 225 km, 3 hours 40 min

  • Basilica of San Francesco d'Assisi
  • Basilica di Santa Chiara
  • Rocca Maggiore
  • Basilica di Santa Maria degli Angeli
  • More

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Santa Maria degli Angeli. The day's journey will conclude in Rome, a city that offers you comfort and relaxation for 3 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, eagerly anticipating your arrival in Santa Maria degli Angeli. This drive usually takes around 32 min, without any stops or traffic disruptions.

Seize the day by visiting some of the best attractions in the area, like Basilica Of San Francesco D'assisi. This extraordinary papal basilica has an average rating of 4.9 out of 5 stars from 33,258 visitors.

Next, make your way to Basilica Di Santa Chiara. This minor basilica is rated an average of 4.7 out of 5 stars in 9,628 reviews.

While in Santa Maria degli Angeli, we also recommend a visit to Rocca Maggiore. Hosting around 22,171 visitors every year, Rocca Maggiore is one of the best places to visit. This rocca has been rated an average of 4.5 out of 5 stars in 3,596 reviews.

Santa Maria degli Angeli’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Santa Maria degli Angeli behind. This drive usually takes around 13 min. Santa Maria degli Angeli welcomes you with a multitude of unique vacation experiences.

When you’re ready for some sightseeing, make your way to Basilica Of Santa Maria Degli Angeli. This much-appreciated papal basilica is rated 4.8 out of 5 stars in 19,258 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.

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

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of mediterranean, and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative, and innovative dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean, and creative menu. With a 2-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 Rome.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Sant' Eustachio Caffè, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

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 – Rome

  • Rome
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Drive 12 km, 1 hour 8 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • More

Day 4 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 2 nights nights remaining.

When you’re ready for some sightseeing, make your way to Colosseum. This much-appreciated roman amphitheatre is rated 4.7 out of 5 stars in 328,821 reviews. Each year, 7,400,000 people visit this site to admire its unique features.

Next up is Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 visitors.

Another top sightseeing recommendation is Trevi Fountain. This sculpture has been rated 4.8 out of 5 stars in 343,494 reviews.

Piazza Di Spagna is another attraction you have the opportunity to visit today. This square has an average rating of 4.7 out of 5 stars from 113,658 reviews.

To continue your sightseeing, head over to Spanish Steps. This monumental staircase is rated an average of 4.5 out of 5 stars in 57,211 reviews.

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.

Enjoy a delicious meal at DEROMA - Farine Romane, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Centro. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Rome this evening.

Following your dinner, dive into the local bar culture at The Apartment Bar Roma. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Hotel Hassler Roma, the perfect place for those looking to experience the best of the nightlife.

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 – Rome

  • Rome
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Drive 11 km, 1 hour 19 min

  • Castel Sant'Angelo
  • Piazza Navona
  • Pantheon
  • Piazza del Popolo
  • Villa Borghese
  • 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 Castel Sant'angelo one of your first sightseeing stops in Rome. Rated an average of 4.7 out of 5 stars by 72,431 travelers, a visit to this local attraction makes for a great introduction to the area. This museum attracts 918,591 visitors every year.

Piazza Navona is a worthwhile attraction you can visit next. This square is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 158,771 reviews.

Today is also the perfect opportunity to drop by Pantheon. This roman temple has been rated an average of 4.8 out of 5 stars by 189,682 visitors. Up to 30,000,000 people travel to this site annually.

If you’re keen to explore more, head to Piazza Del Popolo. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 89,807 previous visitors.

Another top place to visit is Villa Borghese. This urban zone of rome enjoys an average rating of 4.6 out of 5 stars from 69,749 local and international travelers.

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.

Have a fantastic dining experience at Ristorante Tema, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Maccheroni offers an enticing alternative with its varied menu. Additionally, RoYaL Art Cafè Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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 – Rome, Vatican City, and Siena

  • Siena
  • Rome
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Drive 243 km, 3 hours 19 min

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

Start your sightseeing with a visit to Altare Della Patria. This architectural structure is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.8 out of 5 stars by 49,843 visitors. Around 1,683,070 people visit this attraction every year.

Set your GPS to Vatican City, Vatican City and hit the road. Expect a journey of approximately 11 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Vatican City beckons with new experiences!

A top pick for your self-guided sightseeing tour today is St. Peter's Basilica. Over 11,000,000 travelers visit this attraction every year. Previous visitors have rated this major basilica an average of 4.8 out of 5 stars in 131,043 reviews.

Sistine Chapel is a local recommendation that you also can pay a visit today. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Another attraction you won't want to miss is Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars in 133,310 reviews. Every year, around 1,612,530 travelers visit this site to discover its unique features.

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.

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

Have a fantastic dining experience at Antica Trattoria Papei, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria Quattro Venti offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

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

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Day 7

Day 7 – Siena, Pisa, and Florence

  • Florence
  • Siena
  • Pisa
  • More

Drive 216 km, 3 hours 30 min

  • Piazza del Campo
  • Duomo di Siena
  • Leaning Tower of Pisa
  • Piazza del Duomo
  • Camposanto
  • More

Wake up to day 7 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Siena, and Pisa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Piazza Del Campo. This square is rated an average of 4.8 out of 5 stars from 64,175 visitors.

Siena Cathedral is another popular attraction you could visit today. This domus has a rating of 4.8 out of 5 stars from 21,656 visitors.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Pisa. 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 1 hour 50 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

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.

Campo Santo is another attraction you can visit on this day of your vacation. This cemetery has an average rating of 4.6 out of 5 stars by 586 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 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 Florence for you, so you can check out the menus and make your reservation in advance.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative, and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary, and international cuisine in the city.

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 8

Day 8 – Florence - departure day

  • Florence - Departure day
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  • Piazzale Michelangelo
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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 Florence before saying goodbye.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Florence's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Piazzale Michelangelo. This extraordinary square and attraction is rated an average of 4.8 out of 5 stars in 77,744 reviews, and is an excellent choice for your last sightseeing in Florence.

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

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu.

You will then say farewell to Florence 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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