Luxury 5-Day Italy Road Trip from Ancona to Perugia, and Rome

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Set off on the ultimate travel extravagance with this 5-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 Ancona, 1 night in Perugia, 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 5-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 5-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 5-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 Ancona, Loreto, Senigallia, Serra San Quirico, Perugia, Rome, and Teramo 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 – Ancona - arrival day

  • Ancona - Arrival day
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  • Mole Vanvitelliana
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Your luxury holiday in Italy begins as soon as you reach the city of Ancona. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Start your sightseeing with a visit to Lazzaretto Of Ancona. This building is rated an average of 4.4 out of 5 stars from 4,023 visitors.

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

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

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

Continue the enjoyment post-dinner at Posa Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Four Roses offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Amarillo Beer Bar Ancona. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise a toast to the start of your 5-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Ancona, Loreto, Senigallia, Serra San Quirico, and San Vittore

  • Perugia
  • Ancona
  • Loreto
  • Senigallia
  • Serra San Quirico
  • More

Drive 240 km, 3 hours 28 min

  • Passetto
  • Sanctuary of the Holy House of Loreto
  • Rocca Roveresca
  • Parco Naturale Regionale Gola della Rossa e di Frasassi
  • Frasassi Caves
  • More

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Ancona, Loreto, Senigallia, Serra San Quirico, and San Vittore. 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.

Drop by the renowned Passetto. This popular point of interest has been rated an average of 4.5 out of 5 stars by 2,797 visitors.

When you’ve had your share of Ancona, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Loreto. Your travel time is around 32 min.

Drop by the renowned Sanctuary Of The Holy House Of Loreto. This popular church has been rated an average of 4.8 out of 5 stars by 19,100 visitors.

As you’ve unraveled the marvels of Loreto, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Senigallia may take around 41 min. Upon your arrival in Senigallia, you’ll be greeted with the opportunity to do some sightseeing and exploring.

An excellent attraction to start your day with is Rocca Roveresca. This sightseeing destination is rated an average of 4.5 out of 5 stars in 5,207 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.

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 another amazing day of your luxury holiday in Ancona, Italy and seize the opportunity to celebrate.

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Day 3

Day 3 – 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 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 Rome, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Fasten your seatbelt and make your way to your next stop. Vatican City, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Perugia to Vatican City may take around 2 hours 17 min without traffic disruptions. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Begin your sightseeing with a visit to Vatican Museums. This art museum gets 1,612,530 visitors each year and is rated an average of 4.6 out of 5 stars in 133,310 reviews.

Next up, make your way to Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 reviews.

When you’re ready for your next sight of the day, continue to Sistine Chapel. This chapel has an average rating of 4.7 out of 5 stars from 52,083 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit St. Peter's Basilica. This major basilica is rated an average of 4.8 out of 5 stars by 131,043 visitors. Visiting St. Peter's Basilica means you'll be one of 11,000,000 people who do so 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.

Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Rome.

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 excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Sant' Eustachio Caffè, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. 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 – Rome, Teramo, and Ancona

  • Ancona
  • Rome
  • Teramo
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Drive 319 km, 4 hours 16 min

  • Roman Forum
  • Colosseum
  • Pantheon
  • More

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 Rome, and Teramo. 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 Roman Forum. Previous visitors have rated this square an average of 4.7 out of 5 stars in 114,450 reviews.

Colosseum is a local recommendation that you also can pay a visit today. This roman amphitheatre is rated an average of 4.7 out of 5 stars in 328,821 reviews. The attraction welcomes 7,400,000 visitors every year.

Another attraction you won't want to miss is Pantheon. This roman temple is rated an average of 4.8 out of 5 stars in 189,682 reviews. Every year, around 30,000,000 travelers visit this site to discover its unique features.

The attraction gets an estimated 7,400,000 visitors every year.

Set your GPS to Teramo and hit the road. Expect a journey of approximately 2 hours 16 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Teramo beckons with new experiences!

Begin your sightseeing with a visit to Santuario Madonna Delle Grazie. This extraordinary place of worship is rated an average of 4.5 out of 5 stars by 343 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Ancona. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Begin your culinary exploration in Ancona by securing a reservation at Sot'Ajarchi. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of seafood, and from the marches cuisine. Or, for a change of pace, Bontà delle Marche boasts a menu that's sure to impress.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Alla Tazza D'oro, a well-loved spot among locals and tourists.

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

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Day 5

Day 5 – Ancona - departure day

  • Ancona - Departure day
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  • Piazza del Plebiscito
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Today is the last day of your 5-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 Ancona before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Ancona’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 Piazza Del Plebiscito. This extraordinary square and attraction is rated an average of 4.4 out of 5 stars in 2,631 reviews, and is an excellent choice for your last sightseeing in Ancona.

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

If you're in the mood to try something new, consider Mixer Bar, another top spot with a mouthwatering menu.

You will then say farewell to Ancona 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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