Luxury 11-Day Italy Road Trip from Ancona to L'aquila, Rome, Siena, Florence, and Bologna

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!

Make piazza del Plebiscito your first stop of the day. Previous visitors have rated this square an average of 4.4 out of 5 stars in 2,631 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.

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.

Get ready for an unforgettable culinary journey in Ancona by reserving a table at Sot'Ajarchi. Renowned as a Bib Gourmand restaurant, it offers an exceptional seafood and from the marches menu.

After your meal, keep the night alive at a bar like Posa bar, known for its lively atmosphere. Bar four roses is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Amarillo Beer Bar Ancona offers an excellent atmosphere for those looking to amp up the evening.

Raise a toast to the start of your 11-day luxury vacation in Italy and look forward to more fantastic days to come!

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Ancona and Loreto. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Continue your road trip and head to your next destination, Loreto. This car ride takes around 33 min.

Drop by the renowned Porta Pia. This popular city gate has been rated an average of 4.4 out of 5 stars by 130 visitors.

Another unforgettable place to experience is Lazzaretto of Ancona. Rated 4.4 out of 5 stars by 4,023 visitors, this building deserves a spot on today's sightseeing itinerary.

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 33 min.

Make Sanctuary of the Holy House of Loreto one of your first sightseeing stops in Loreto. Rated an average of 4.8 out of 5 stars by 19,100 travelers, a visit to this local attraction makes for a great introduction to the area.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in L'aquila.

After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in L'aquila. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Set out on a gastronomic journey in L'aquila by reserving a table at FØRMA contemporary restaurant. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of contemporary and creative cuisine. With its reputation for pleasing customers, it’s a fantastic choice for tonight in L'aquila.

Extend your evening after a delightful meal by visiting Art Cafè L'Aquila, which offers the perfect atmosphere for a night out.

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

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 3 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Vatican City welcomes you with a multitude of unique vacation experiences.

When you're ready to see some sights, Vatican Museums is a great place to start. This art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Vatican Museums attracts more than 1,612,530 visitors every year.

Another popular attraction you can visit today is Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 travelers.

We also recommend a stop at Sistine Chapel. The chapel has been rated an average of 4.7 out of 5 stars by 52,083 visitors.

If you're keen to explore more, consider visiting St. Peter's Basilica. This major basilica is a popular attraction with an average rating of 4.8 out of 5 stars from 131,043 reviews. As a top-rated attraction, it's no surprise that 11,000,000 people visit St. Peter's Basilica every year.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Rome.

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.

Treat yourself to an extraordinary dining experience at La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated it is an ideal choice for mediterranean and creative cuisine in the city.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Sant' Eustachio Caffè offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino is also a great option that provides a perfect setting for a relaxing evening.

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 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.

An excellent attraction to start your day with is Altare della Patria. This architectural structure typically receives around 1,683,070 visitors every year and is rated an average of 4.8 out of 5 stars in 49,843 reviews.

Continue your journey at Capitoline Hill. This hill is rated 4.7 out of 5 stars by 19,557 travelers from near and far.

Rome is also the home of Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 visitors.

You can continue your self-guided sightseeing tour at Colosseum. A total of 7,400,000 people explore this attraction every year. Rated 4.7 out of 5 stars by 328,821 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Circus Maximus. With an average rating of 4.4 out of 5 stars from 44,741 reviews, it’s hard to refuse the opportunity to see this circus.

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.

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

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

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.

Start your sightseeing with a visit to Castel Sant'Angelo. This museum is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.7 out of 5 stars by 72,431 visitors. Around 918,591 people visit this attraction every year.

Piazza Navona is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 158,771 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Pantheon. Visitors have rated this roman temple an average of 4.8 out of 5 stars in 189,682 reviews. Pantheon receives around 30,000,000 visitors every year.

Largo di Torre Argentina is another unique site you can experience today. This attraction is a square rated an average of 4.5 out of 5 stars in 30,433 reviews.

Make your way to the fantastic Campo de' Fiori, perhaps the most famous square in Rome. This attraction is rated 4.4 out of 5 stars by 51,133 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.

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.

Wake up to day 6 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.

As you’ve unraveled the marvels of Rome, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Siena may take around 2 hours 41 min. Upon your arrival in Siena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Seize the day by visiting some of the best attractions in the area, like Trevi Fountain. This extraordinary sculpture has an average rating of 4.8 out of 5 stars from 343,494 visitors.

Next, make your way to Piazza di Spagna. This square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

While in Rome, we also recommend a visit to Spanish Steps. This monumental staircase has been rated an average of 4.5 out of 5 stars in 57,211 reviews.

If you’re keen to explore even more, then consider a visit to piazza del Popolo. With an average rating of 4.6 out of 5 stars by 89,807 travelers, this square is a highly recommended stop on your sightseeing around Rome.

Make your way to Villa Borghese, perhaps the most famous urban zone of rome in Rome. This attraction is rated an average of 4.6 out of 5 stars in 69,749 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Siena.

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.

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.

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.

On day 7 of your luxury holiday in Italy, your road trip route will take you exploring the best of Siena and Pisa. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Fasten your seatbelt and make your way to your next stop. Pisa, 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 Siena to Pisa may take around 1 hour 48 min without traffic disruptions. Upon arrival in Pisa, we highly recommend checking out some of the top attractions.

Make Tower of Mangia your first stop of the day. Previous visitors have rated this sightseeing destination an average of 4.6 out of 5 stars in 673 reviews.

Next up, make a stop at piazza del Campo. With an average rating of 4.8 out of 5 stars by 64,175 visitors, it's easy to understand why so many people visit this square every year.

Siena Cathedral is another attraction you can visit on this day of your vacation. This domus has an average rating of 4.8 out of 5 stars by 21,656 visitors.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 48 min. When you arrive, enjoy some sightseeing.

Seize the day by visiting some of the best attractions in the area, like Piazza del Duomo, Pisa. This extraordinary square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Next, make your way to Leaning Tower of Pisa. This bell tower welcomes around 3,200,000 visitors yearly and is rated an average of 4.7 out of 5 stars in 116,882 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Florence.

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

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Following your dinner, dive into the local bar culture at Manifattura. 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.

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

Day 8 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.

Begin your sightseeing with a visit to Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Next up, make your way to Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars from 61,794 reviews. Usually, around 2,011,219 people visit Uffizi Gallery every year.

When you’re ready for your next sight of the day, continue to piazza della Signoria. This square has an average rating of 4.8 out of 5 stars from 66,956 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Basilica of Santa Croce in Florence. This church is rated an average of 4.7 out of 5 stars by 28,544 visitors.

If you’re keen to explore even more, then consider a visit to piazzale Michelangelo. This square is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 77,744 visitors.

Discover a world of culinary delights in Florence, 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.

This renowned restaurant holds , and offers an exceptional menu of cuisine.

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

Wake up to day 9 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 Bologna, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Bologna. This drive usually takes around 1 hour 24 min. When you arrive, enjoy some sightseeing.

Begin your sightseeing with a visit to Cathedral of Santa Maria del Fiore. This extraordinary church is rated an average of 4.8 out of 5 stars by 76,359 visitors.

Next, make your way to Galleria dell'Accademia. This top attraction is a national museum with an average rating of 4.6 out of 5 stars by 34,429 visitors. Galleria dell'Accademia welcomes 1,719,645 yearly visitors.

We also recommend a visit to Central Market. This point of interest is rated 4.4 out of 5 stars by 43,100 travelers.

If you’re keen to keep exploring, visit Basilica di Santa Maria Novella, Firenze (FI). This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 23,075 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Bologna.

Discover a world of culinary delights in Bologna, 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 an outstanding dining experience at I Portici, a 1-star Michelin restaurant offering an exceptional creative and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby Bib Gourmand-awardee, Ahimè, known for its delicious country cooking cuisine. Another highly-recommended restaurant in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant , known for its delicious emilian menu.

Unwind after your meal by stepping into Bar Freud e Squisito. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Osteria del Sole offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Macondo - Cocktail Bar, 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.

Wake up to day 10 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Ancona. Your travel time is around 2 hours 22 min.

Begin your sightseeing with a visit to Piazza Maggiore. This square is rated an average of 4.7 out of 5 stars in 64,523 reviews.

Next up, make your way to Bologna Cathedral. This catholic cathedral has an average rating of 4.6 out of 5 stars from 3,852 reviews.

When you’re ready for your next sight of the day, continue to Two Towers. This tower has an average rating of 4.7 out of 5 stars from 25,975 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza Santo Stefano. This square is rated an average of 4.8 out of 5 stars by 7,617 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Ancona.

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

After savoring a delicious meal, step into the vibrant nightlife at Alla Tazza D'Oro, where the evening is just getting started.

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

Today is the last day of your 11-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.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Ancona’s celebrated shopping district. Thanks to your stay’s premier location, you can easily visit the city’s commercial hubs and wander through its diverse range of local shops without rushing.

Whether you’re on a hunt for an ideal present to give to your friends or family or looking for a personal memento to remind you of Italy, a variety of items are waiting for you. Hold onto the magic of Italy with these wonderful souvenirs, ensuring your memories never fade.

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!