Luxury 6-Day Italy Road Trip from Ancona traveling west to L'aquila, Rome, and Siena

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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 Ancona, 1 night in L'aquila, 1 night 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 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 Ancona, Loreto, L'aquila, Rome, Siena, 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

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, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

When you’re ready for some sightseeing, make your way to Lazzaretto Of Ancona. This much-appreciated building is rated 4.4 out of 5 stars in 4,023 reviews.

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.

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

Don’t miss out on dining at Playa Solero, a top-rated dining destination in Ancona. If you're in the mood to try something new, consider Zucchero a Velò, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Il Giardino. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Ancona this evening.

Extend your evening after a delightful meal by visiting Posa Bar, which offers the perfect atmosphere for a night out. Moreover, Bar Four Roses is another popular option for a drink or two. Likewise, Amarillo Beer Bar Ancona also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 – Ancona, San Vittore, Loreto, and L'aquila

  • L'Aquila
  • Ancona
  • Loreto
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Drive 312 km, 3 hours 56 min

  • Frasassi Caves
  • Sanctuary of the Holy House of Loreto
  • 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 L'aquila, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Ancona, San Vittore, and Loreto.

Drop by the renowned Parco Belvedere Posatora. This popular park has been rated an average of 4.5 out of 5 stars by 1,009 visitors.

Fasten your seatbelt and make your way to your next stop. San Vittore, 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 Ancona to San Vittore may take around 42 min without traffic disruptions. Upon arrival in San Vittore, we highly recommend checking out some of the top attractions.

Take the opportunity to see Frasassi Caves. This attraction has an average rating of 4.8 out of 5 stars from 20,728 visitors.

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

When you're ready to see some sights, Sanctuary Of The Holy House Of Loreto is a great place to start. This church is rated an average of 4.8 out of 5 stars by 19,100 visitors.

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

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

Experience a symphony of flavors at FØRMA contemporary restaurant in L'aquila by securing a reservation in advance. Renowned for its Bib Gourmand distinction, FØRMA contemporary restaurant delights its guests with its exceptional variety of meals showcasing delicious contemporary, and creative cuisine. Or, if you're feeling adventurous, why not try DECA? It's another excellent option with a diverse menu.

Cap off your dinner by heading to Art Cafè L'aquila, ideal for a leisurely evening with a drink in hand.

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 3

Day 3 – L'aquila, Vatican City, and Rome

  • Rome
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Drive 135 km, 2 hours 21 min

  • Vatican Museums
  • Saint Peter's Square
  • Sistine Chapel
  • St Peter's Basilica
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On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. The day's journey will conclude in Rome, 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.

Embrace the thrill of the open road as you wave goodbye to L'aquila and set your GPS to Vatican City, Vatican City. 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 38 min. Upon reaching Vatican City, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

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.

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.

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.

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.

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

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Day 4

Day 4 – Rome, and Siena

  • Siena
  • Rome
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Drive 243 km, 3 hours 31 min

  • Roman Forum
  • Colosseum
  • Piazza Navona
  • Pantheon
  • Trevi Fountain
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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 Rome. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Your sightseeing of the day begins at Roman Forum, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Next, satisfy your wanderlust at Colosseum. This roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 travelers. Given the site's popularity, it’s easy to understand why more than 7,400,000 people visit it every year.

Piazza Navona is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 158,771 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 Pantheon. This well-loved roman temple boasts a 4.8 out of 5-star rating from 189,682 reviews. In a single year, approximately 30,000,000 visitors add this sightseeing spot to their travel itineraries.

When there’s still energy left for exploring, Trevi Fountain awaits. If you’ve been interested in experiencing a sculpture, this is a top pick rated 4.8 out of 5 stars by 343,494 previous visitors.

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 day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Siena. Savor the local cuisine and relax as you recount the day's experiences.

Enjoy a lovely meal at Antica Trattoria Papei, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Quattro Venti is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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 5

Day 5 – Siena, Santa Maria degli Angeli, and Ancona

  • Ancona
  • Siena
  • Assisi
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Drive 257 km, 4 hours

  • Piazza del Campo
  • Duomo di Siena
  • Fortezza Medicea
  • Basilica of San Francesco d'Assisi
  • 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 Ancona, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Siena, and Santa Maria degli Angeli.

When you’re ready for some sightseeing, make your way to Piazza Del Campo. This much-appreciated square is rated 4.8 out of 5 stars in 64,175 reviews.

Next up is Siena Cathedral. This domus has an average rating of 4.8 out of 5 stars from 21,656 visitors.

Another top sightseeing recommendation is Fortezza Medicea (siena). This fortress has been rated 4.5 out of 5 stars in 9,835 reviews.

As you’ve unraveled the marvels of Siena, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Santa Maria degli Angeli may take around 1 hour 41 min. Upon your arrival in Santa Maria degli Angeli, you’ll be greeted with the opportunity to do some sightseeing and exploring.

An excellent attraction to start your day with is Basilica Of San Francesco D'assisi. 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 Ancona. 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 Ancona so you can check out the menus and make advance reservations.

Experience a taste of local culinary excellence while in Ancona by securing a table at Sot'Ajarchi. An esteemed Bib Gourmand restaurant, it features an exceptional seafood, and from the marches menu. If you're in the mood for something new, try Bontà delle Marche, another premier location with a delectable menu.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Alla Tazza D'oro, known for its inviting atmosphere.

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 – Ancona - departure day

  • Ancona - Departure day
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  • Passetto
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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 Ancona before saying goodbye.

Make the most of your final day in Italy by visiting Ancona’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 Passetto. This extraordinary sightseeing destination and attraction is rated an average of 4.5 out of 5 stars in 2,797 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.

Enjoy a lovely meal at Vino E Cucina Miscia, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Mixer Bar is another top choice with a popular 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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