Luxury 10-Day Italy Road Trip from Ancona traveling west to Rimini, Florence, Siena, and Rome

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!

An excellent attraction to start your day with is Parco Della Cittadella di Ancona. This park is rated an average of 4.4 out of 5 stars in 843 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.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Posa bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, bar four roses offers an ideal atmosphere to enjoy the pleasures of the night. Amarillo Beer Bar Ancona is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to the start of your 10-day luxury vacation in Italy and look forward to more fantastic days to come!

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 Rimini, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Serra San Quirico, San Vittore, Senigallia, and Loreto.

Fasten your seatbelt and make your way to your next stop. Serra San Quirico, 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 San Vittore to Serra San Quirico may take around 16 min without traffic disruptions. Upon arrival in Serra San Quirico, we highly recommend checking out some of the top attractions.

An excellent attraction to start your day with is Parco Naturale Regionale Gola della Rossa e di Frasassi. This park is rated an average of 4.6 out of 5 stars in 3,515 reviews.

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 Loreto to San Vittore may take around 55 min without traffic disruptions. Upon arrival in San Vittore, we highly recommend checking out some of the top attractions.

Be one of the day’s first visitors at Frasassi Caves. This show cave is rated an average of 4.8 out of 5 stars by 20,728 visitors.

Set your GPS to Senigallia and hit the road. Expect a journey of approximately 50 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Senigallia beckons with new experiences!

Begin your sightseeing with a visit to 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 in Rimini.

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

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Caffè Il Borgo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Primo Bacio città Lounge Bar offers an ideal atmosphere to enjoy the pleasures of the night. Hobo's 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 luxury holiday in Italy has plenty more in store for you.

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rimini and Bologna. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

As you’ve unraveled the marvels of Rimini, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Bologna may take around 1 hour 24 min. Upon your arrival in Bologna, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready to see some sights, Piazza Cavour is a great place to start. This point of interest is rated an average of 4.5 out of 5 stars by 11,447 visitors.

Another popular attraction you can visit today is Arch of Augustus. This triumphal arch has an average rating of 4.6 out of 5 stars from 12,375 travelers.

Embrace the thrill of the open road as you wave goodbye to Rimini and set your GPS to Bologna. 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 24 min. Upon reaching Bologna, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Your sightseeing of the day begins at Piazza Santo Stefano, 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 7,617 reviews.

Next, satisfy your wanderlust at Two Towers. This tower has an average rating of 4.7 out of 5 stars from 25,975 travelers.

Piazza Maggiore 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 64,523 travelers, it's one of the more popular places to see in the area.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, SE·STO on Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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.

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 Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 3 min.

Start your sightseeing with a visit to piazza della Signoria. This square is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 66,956 visitors.

Cathedral of Santa Maria del Fiore is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 76,359 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Ponte Vecchio. Visitors have rated this deck arch bridge an average of 4.7 out of 5 stars in 118,099 reviews.

Uffizi Gallery, boasting an annual visitor count of up to 2,011,219 people, is another unique site you can experience today. This attraction is a national museum rated an average of 4.7 out of 5 stars in 61,794 reviews.

Make your way to the fantastic piazzale Michelangelo, perhaps the most famous square in Florence. This attraction is rated 4.8 out of 5 stars by 77,744 travelers.

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

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

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

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 Rome, where you'll be staying for 4 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Vatican City.

Your sightseeing of the day begins at Sistine Chapel, a remarkable chapel where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Next, satisfy your wanderlust at St. Peter's Basilica. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 travelers. Given the site's popularity, it’s easy to understand why more than 11,000,000 people visit it every year.

Saint Peter's Square 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 38,954 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 Vatican Museums. This well-loved art museum boasts a 4.6 out of 5-star rating from 133,310 reviews. In a single year, approximately 1,612,530 visitors add this sightseeing spot to their travel itineraries.

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

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 Rome for you, so you can check out the menus and make your reservation in advance.

Continue the enjoyment post-dinner at La Botticella of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Sant' Eustachio Caffè offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffè Portofino. 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 another amazing day of your luxury holiday in Vatican City, Italy and seize the opportunity to celebrate.

Day 6 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 3 nights nights remaining.

Be one of the day’s first visitors at Villa Borghese. This urban zone of rome is rated an average of 4.6 out of 5 stars by 69,749 visitors.

When you’re finished at Villa Borghese, head to piazza del Popolo. This one-of-a-kind square is rated an average of 4.6 out of 5 stars in 89,807 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Castel Sant'Angelo. This museum is rated an average of 4.7 out of 5 stars by 72,431 visitors. Visiting Castel Sant'Angelo means you'll be one of 918,591 people who do so every year.

If you’re keen to explore more, then consider a visit to Piazza Navona. This square is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 158,771 visitors.

To round off your sightseeing experience, make your way to Campo de' Fiori. This famous square is rated an average of 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.

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

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

Day 7 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.

A top pick for your self-guided sightseeing tour today is Colosseum. Over 7,400,000 travelers visit this attraction every year. Previous visitors have rated this roman amphitheatre an average of 4.7 out of 5 stars in 328,821 reviews.

Roman Forum is a local recommendation that you also can pay a visit today. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Another attraction you won't want to miss is Trevi Fountain. This sculpture is rated an average of 4.8 out of 5 stars in 343,494 reviews.

Piazza di Spagna is another outstanding experience in Rome. Around 113,658 travelers have rated this square an average of 4.7 out of 5 stars.

If you long for more, Spanish Steps is not far away. This monumental staircase is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.5 out of 5 stars in 57,211 reviews.

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

Esteemed as a restaurant, it features an exceptional menu.

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 8 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 Basilica di Santa Maria Maggiore one of your first sightseeing stops in Rome. Rated an average of 4.8 out of 5 stars by 27,678 travelers, a visit to this local attraction makes for a great introduction to the area.

Circus Maximus is a worthwhile attraction you can visit next. This circus is a valued place of interest in the area, with an average rating of 4.4 out of 5 stars from 44,741 reviews.

Today is also the perfect opportunity to drop by Altare della Patria. This architectural structure has been rated an average of 4.8 out of 5 stars by 49,843 visitors. Up to 1,683,070 people travel to this site annually.

If you’re keen to explore more, head to largo di Torre Argentina. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.5 out of 5-star rating as given by 30,433 previous visitors.

Another top place to visit is Pantheon. This roman temple enjoys an average rating of 4.8 out of 5 stars from 189,682 local and international travelers. Approximately 30,000,000 people visit this attraction every year.

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

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

After soaking in Tivoli’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Teramo. Expect your car journey to take a minimum of 1 hour 42 min. When you arrive in Teramo, it's time to take a break from the road.

Kick off the day at Santuario Madonna Delle Grazie, a top pick for today’s sightseeing. This place of worship is rated an average of 4.5 out of 5 stars in 343 reviews.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Tivoli. Your travel time is around 38 min.

Seize the day by visiting some of the best attractions in the area, like Hadrian's Villa. This extraordinary archaeological site has an average rating of 4.6 out of 5 stars from 9,813 visitors. Each year, around 77,557 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Villa d'Este. This giardino all'italiana welcomes around 139,855 visitors yearly and is rated an average of 4.7 out of 5 stars in 25,000 reviews.

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

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

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.

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.

Today is the last day of your 10-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 your final day in Italy unfolds, don’t miss the chance for a last-minute shopping spree in Ancona’s shopping district. Your accommodation’s convenient location near the city’s shopping area offers the luxury of time, so you don’t have to limit yourself from leisurely strolling its streets amidst a collection of establishments.

Look for the perfect gift for your loved ones back home, or buy yourself a little keepsake to remind you of Italy. Keep the spirit of your trip to Italy alive with these special souvenirs.

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

Treat yourself to a delicious dinner at Vino E Cucina Miscia, an excellent option for tonight's dining. Looking for something different? Mixer Bar offers a tantalizing alternative with its diverse menu. And don’t miss La Cantineta.

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!