Luxury 9-Day Italy Road Trip from Perugia to Rome, Siena, and Florence
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Experience travel that redefines comfort and elegance with this 9-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 Perugia, 3 nights in Rome, 1 night in Siena, and 2 nights in Florence, 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 9-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 9-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 9-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, Rome, Siena, Pisa, Florence, and Santa Maria degli Angeli 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 – Perugia - arrival day
- Perugia - Arrival day
- More
- Etruscan Arch
- More
Your luxury holiday in Italy begins as soon as you reach the city of Perugia, where you'll be staying for 1 night. 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 Etruscan Arch. This architectural element is rated an average of 4.7 out of 5 stars in 1,190 reviews.
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.
In Perugia, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.
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.
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 9-day luxury vacation in Italy and look forward to more fantastic days to come!
Day 2 – Perugia, and Rome
- Rome
- Perugia
- More
Drive 183 km, 2 hours 27 min
- The Fontana Maggiore
- Piazza IV Novembre
- National Gallery
- Chiesa del Gesù
- More
On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Perugia. 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.
Journey into the unknown at The Fontana Maggiore, a unique attraction awaiting your visit. This remarkable sightseeing destination has an average rating of 4.7 out of 5 stars from 612 reviews.
When you’re ready to continue your sightseeing, Piazza IV Novembre is a recommended place to visit. This square is rated an average of 4.6 out of 5 stars in 9,189 reviews.
Another must-see attraction in Perugia is National Gallery. Rated an average of 4.6 out of 5 stars by 1,294 travelers, this popular tourist destination in Perugia offers an experience you will remember.
Chiesa del Gesù is another popular stop on travelers' itineraries in Perugia. This church promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 116 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.
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.
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 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.
Raise a toast to another amazing day of your luxury holiday in Perugia, Italy and seize the opportunity to celebrate.
Day 3 – Rome
- Rome
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Drive 14 km, 1 hour 12 min
- Villa Borghese
- Trevi Fountain
- Piazza di Spagna
- Spanish Steps
- Piazza del Popolo
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Day 3 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 to see some sights, Villa Borghese is a great place to start. This urban zone of rome is rated an average of 4.6 out of 5 stars by 69,749 visitors.
Another popular attraction you can visit today is Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars from 343,494 travelers.
We also recommend a stop at Piazza di Spagna. The square has been rated an average of 4.7 out of 5 stars by 113,658 visitors.
If you're keen to explore more, consider visiting Spanish Steps. This monumental staircase is a popular attraction with an average rating of 4.5 out of 5 stars from 57,211 reviews.
Piazza del Popolo is another easily accessible place to visit on this day of your trip. Stop by this square, rated 4.6 out of 5 stars in 89,807 reviews, to discover more of what makes it unique.
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 Rome so you can check out the menus and make advance reservations.
Treat yourself to a wonderful meal at DEROMA - Farine Romane, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at Centro. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.
Raise your glass and relax after another big day of your luxury holiday in Italy!
Day 4 – Rome
- Rome
- More
Drive 7 km, 1 hour 17 min
- Piazza Navona
- Castel Sant'Angelo
- Altar of the Fatherland
- Roman Forum
- Colosseum
- 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 1 night nights remaining.
A top pick for your self-guided sightseeing tour today is Piazza Navona. Previous visitors have rated this square an average of 4.7 out of 5 stars in 158,771 reviews.
Castel Sant'Angelo is a local recommendation that you also can pay a visit today. This museum is rated an average of 4.7 out of 5 stars in 72,431 reviews. The attraction welcomes 918,591 visitors every year.
Another attraction you won't want to miss is Altare della Patria. This architectural structure is rated an average of 4.8 out of 5 stars in 49,843 reviews. Every year, around 1,683,070 travelers visit this site to discover its unique features.
Roman Forum is another outstanding experience in Rome. Around 114,450 travelers have rated this square an average of 4.7 out of 5 stars.
If you long for more, Colosseum is not far away. This roman amphitheatre is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.7 out of 5 stars in 328,821 reviews. The attraction gets an estimated 918,591 visitors every year.
Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Rome.
Treat yourself to a delightful dinner at Ristorante Tema, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Maccheroni? It's another excellent option with a diverse menu. Consider reserving a table at RoYaL Art Cafè Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.
Day 5 – Rome, Vatican City, and Siena
- Siena
- Rome
- More
Drive 243 km, 3 hours 26 min
- Pantheon
- St Peter's Basilica
- Sistine Chapel
- Vatican Museums
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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 Rome, and Vatican City. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.
Seize the day by visiting some of the best attractions in the area, like Pantheon. This extraordinary roman temple has an average rating of 4.8 out of 5 stars from 189,682 visitors. Each year, around 30,000,000 people visit this remarkable site to admire its features and learn more about it.
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!
Journey into the unknown at St. Peter's Basilica, a unique attraction awaiting your visit. This remarkable major basilica has an average rating of 4.8 out of 5 stars from 131,043 reviews. Every year, St. Peter's Basilica welcomes more than 11,000,000 curious visitors.
When you’re ready to continue your sightseeing, Sistine Chapel is a recommended place to visit. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.
Another must-see attraction in Vatican City is Vatican Museums. This spectacular art museum gets over 1,612,530 visitors every year. Rated an average of 4.6 out of 5 stars by 133,310 travelers, this popular tourist destination in Vatican City offers an experience you will remember.
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 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 Siena for you, so you can check out the menus and make your reservation in advance.
Dine in style at Antica Trattoria Papei, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Quattro Venti boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.
Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.
Raise your glass and relax after another big day of your luxury holiday in Italy!
Day 6 – Siena, Pisa, and Florence
- Florence
- Siena
- Pisa
- More
Drive 222 km, 3 hours 29 min
- Piazza del Campo
- Facciatone
- Duomo di Siena
- Piazza del Duomo
- Leaning Tower of Pisa
- 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 Florence, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Siena, and Pisa.
Take the opportunity to see piazza del Campo. This attraction has an average rating of 4.8 out of 5 stars from 64,175 visitors.
Facciatone is another sightseeing hotspot in the area. This sightseeing destination has been rated an average of 4.3 out of 5 stars by 252 travelers.
Siena is also the home of Siena Cathedral. Around 21,656 people have rated this domus an average of 4.8 out of 5 stars.
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 48 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.
An excellent attraction to start your day with is Piazza del Duomo, Pisa. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.
Continue your journey at Leaning Tower of Pisa. This bell tower is rated 4.7 out of 5 stars by 116,882 travelers from near and far. Approximately 3,200,000 people come to this place of interest every year to enjoy a unique experience in Pisa.
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.
Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative, and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary, and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.
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.
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.
Day 7 – Florence
- Florence
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Drive 4 km, 1 hour 6 min
- Piazzale Michelangelo
- Basilica of Santa Croce in Florence
- Piazza della Signoria
- Ponte Vecchio
- Uffizi Gallery
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Day 7 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.
Your sightseeing of the day begins at piazzale Michelangelo, 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 77,744 reviews.
Next, satisfy your wanderlust at Basilica of Santa Croce in Florence. This church has an average rating of 4.7 out of 5 stars from 28,544 travelers.
Piazza della Signoria is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 66,956 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.
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 Florence for you so you can browse their menus in advance and make a reservation.
Have a fantastic dining experience at Trattoria Da Burde, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Buca Mario offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.
Raise a toast to another amazing day of your luxury holiday in Florence, Italy and seize the opportunity to celebrate.
Day 8 – Florence, Santa Maria degli Angeli, and Perugia
- Perugia
- Florence
- Assisi
- More
Drive 194 km, 3 hours
- Cathedral of Santa Maria del Fiore
- Central Market
- Accademia Gallery
- Basilica of San Francesco d'Assisi
- More
On day 8 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence, and Santa Maria degli Angeli. The day's journey will conclude in Perugia, 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.
Start your sightseeing with a visit to Cathedral of Santa Maria del Fiore. This church is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 76,359 visitors.
Central Market is another popular place of interest you can visit today. The average rating of 4.4 out of 5 stars from 43,100 reviews gives you an idea of other visitors’ experience at this attraction.
If it’s still bright and early, make your way to Galleria dell'Accademia. Visitors have rated this national museum an average of 4.6 out of 5 stars in 34,429 reviews. Galleria dell'Accademia receives around 1,719,645 visitors every year.
When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Santa Maria degli Angeli. This drive usually takes around 2 hours 7 min. When you arrive, enjoy some sightseeing.
Kick off the day at Basilica of San Francesco d'Assisi, a top pick for today’s sightseeing. This papal basilica is rated an average of 4.9 out of 5 stars in 33,258 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.
Discover a world of culinary delights in Perugia, 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 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.
Unwind after your meal by stepping into Caffè Fortebraccio. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Caffe Del Banco offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Dempsey's Perugia, another top-rated bar in the area.
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.
Day 9 – Perugia - departure day
- Perugia - Departure day
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- Rocca Paolina
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Today is the last day of your 9-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.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Perugia'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 Rocca Paolina. This extraordinary rocca and attraction is rated an average of 4.7 out of 5 stars in 7,128 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.
Treat yourself to a delicious dinner at Sangallo Palace Hotel, an excellent option for tonight's dining. Looking for something different? Osteria a Priori offers a tantalizing alternative with its diverse menu. And don’t miss La Bottega di Perugia.
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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