Luxury Two-Week Italy Road Trip from Ancona to Bologna, Venice, Milan, Genoa, Florence, Siena, and Rome

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Set off on the ultimate travel extravagance with this 15-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 Bologna, 1 night in Venice, 2 nights in Milan, 1 night in Genoa, 2 nights in Florence, 1 night in Siena, and 4 nights 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 15-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 15-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 15-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, Bologna, Padua, Venice, Valeggio sul Mincio, Milan, Verona, Genoa, Pisa, Florence, Siena, Rome, Tivoli, 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
  • More
  • Parco Della Cittadella di Ancona
  • More

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 Parco Della Cittadella Di Ancona your first stop of the day. Previous visitors have rated this park 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.

Discover a world of culinary delights in Ancona, 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 Playa Solero, a top-rated dining spot in Ancona. If you're in the mood for something new, try Zucchero a Velò, another premier location with a delectable menu. You might also want to book a table at Ristorante Il Giardino. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.

Following your dinner, dive into the local bar culture at Posa Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Four Roses, the perfect place for those looking to experience the best of the nightlife. Similarly, Amarillo Beer Bar Ancona provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise a toast to the start of your 15-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Ancona, Loreto, and Bologna

  • Bologna
  • Ancona
  • Loreto
  • More

Drive 275 km, 3 hours 28 min

  • Museo Archeologico Nazionale delle Marche
  • Cattedrale di San Ciriaco
  • Sanctuary of the Holy House of Loreto
  • More

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Ancona, and Loreto. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

When you’re ready for some sightseeing, make your way to Museo Archeologico Nazionale Delle Marche. This much-appreciated archaeological museum is rated 4.5 out of 5 stars in 406 reviews. Each year, 3,696 people visit this site to admire its unique features.

Next up is Cathedral Basilica Of St. Cyriacus. This cathedral has an average rating of 4.6 out of 5 stars from 2,724 visitors.

Fasten your seatbelt and make your way to your next stop. Loreto, 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 Loreto may take around 35 min without traffic disruptions. Upon arrival in Loreto, we highly recommend checking out some of the top attractions.

Start your sightseeing with a visit to Sanctuary Of The Holy House Of Loreto. This church is a popular stop on travelers’ itineraries in Loreto, with an average rating 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 Bologna. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Experience a symphony of flavors at I Portici in Bologna by securing a reservation in advance. Renowned for its 1-star Michelin distinction, I Portici delights its guests with its exceptional variety of meals showcasing delicious creative, and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Ahimè, acclaimed for its delectable country cooking specialties. This local Bib Gourmand establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Trattoria di Via Serra, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for emilian cuisine in the city.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Freud E Squisito, known for its inviting atmosphere. Osteria Del Sole is another great option if you’re looking for a place to get the night started. Similarly, Macondo - Cocktail Bar provides a great setting to enjoy the night away.

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

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Day 3

Day 3 – Bologna, Padua, and Venice

  • Venice
  • Bologna
  • Padua
  • More

Drive 156 km, 2 hours 27 min

  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • The Basilica of St Anthony
  • Prato della Valle
  • More

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 Venice, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Bologna, and Padua.

Make Piazza Maggiore one of your first sightseeing stops in Bologna. Rated an average of 4.7 out of 5 stars by 64,523 travelers, a visit to this local attraction makes for a great introduction to the area.

Two Towers is a worthwhile attraction you can visit next. This tower is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 25,975 reviews.

Today is also the perfect opportunity to drop by Piazza Santo Stefano. This square has been rated an average of 4.8 out of 5 stars by 7,617 visitors.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Padua. This drive usually takes around 1 hour 28 min, without any stops or traffic disruptions.

Take the opportunity to see The Basilica Of St. Anthony. This attraction has an average rating of 4.8 out of 5 stars from 38,852 visitors.

Prato Della Valle is another sightseeing hotspot in the area. This square has been rated an average of 4.6 out of 5 stars by 47,576 travelers.

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

Experience a taste of local culinary excellence while in Venice by securing a table at Local. An esteemed 1-star Michelin restaurant, it features an exceptional contemporary menu. For an alternative taste experience, visit Wistèria, famous for its scrumptious contemporary, and venetian dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Quadri, a local favorite celebrated for its exquisite modern cuisine in Venice. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for modern cuisine lovers seeking top-notch culinary experiences.

Extend your evening after a delightful meal by visiting Al Parlamento, which offers the perfect atmosphere for a night out. Moreover, Adagio is another popular option for a drink or two. Likewise, Il Mercante also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 4

Day 4 – Venice, Valeggio sul Mincio, and Milan

  • Milan
  • Venice
  • Valeggio sul Mincio
  • More

Drive 289 km, 3 hours 57 min

  • Rialto Bridge
  • St. Mark's Square
  • Doge's Palace
  • Parco Giardino Sigurtà
  • More

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Venice, and Valeggio sul Mincio. The day's journey will conclude in Milan, a city that offers you comfort and relaxation for 2 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.

Drop by the renowned Rialto Bridge. This popular stone bridge has been rated an average of 4.7 out of 5 stars by 141,666 visitors.

Another unforgettable place to experience is Piazza San Marco. Rated 4.7 out of 5 stars by 152,982 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Doge's Palace. Hosting around 318,104 visitors every year, the fascinating Doge's Palace is one of the best places to visit in Venice. This palace has been rated an average of 4.7 out of 5 stars in 24,775 reviews.

As you’ve unraveled the marvels of Venice, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Valeggio sul Mincio may take around 1 hour 41 min. Upon your arrival in Valeggio sul Mincio, 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 Parco Giardino Sigurtà. This extraordinary park has an average rating of 4.6 out of 5 stars from 27,387 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. 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 Milan for you so you can browse their menus in advance and make a reservation.

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international, and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary, and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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

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 5

Day 5 – Milan, and Verona

  • Milan
  • Verona
  • More

Drive 332 km, 4 hours 34 min

  • Verona Arena
  • Piazza Gae Aulenti
  • Arco della Pace
  • Milan Natural History Museum
  • More

On day 5 of your luxury road trip in Italy, you’ll start and end your day in the city of Milan, but jump in the car to visit amazing attractions in the nearby area. After a day of sightseeing, you'll drive back to Milan, where you still have 1 night left.

A top pick for your self-guided sightseeing tour today is Piazza Gae Aulenti. Previous visitors have rated this square an average of 4.6 out of 5 stars in 30,398 reviews.

Arch Of Peace is a local recommendation that you also can pay a visit today. This monument is rated an average of 4.6 out of 5 stars in 27,502 reviews.

Another attraction you won't want to miss is Milan Natural History Museum. This museum is rated an average of 4.4 out of 5 stars in 8,412 reviews.

Set your GPS to Verona and hit the road. Expect a journey of approximately 2 hours 7 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Verona beckons with new experiences!

Take the opportunity to see Verona Arena. This attraction has an average rating of 4.7 out of 5 stars from 123,818 visitors and gets around 195,540 visits every year.

When you’ve completed everything you want to see and do, you will drive back to your luxury accommodation in Milan.

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

Dine in style at Nero 9, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante la Brisa boasts a menu that's sure to impress. Also, be sure to check out UNAHOTELS Cusani Milano. Known as a local hotspot, it’s a great choice for tonight in Milan.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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 – Milan, and Genoa

  • Genoa
  • Milan
  • More

Drive 149 km, 2 hours 31 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Teatro alla Scala
  • Sforzesco Castle
  • Sempione Park
  • More

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

An excellent attraction to start your day with is Duomo Di Milano Museum. This art museum typically receives around 341,609 visitors every year and is rated an average of 4.8 out of 5 stars in 138,554 reviews.

Continue your journey at Galleria Vittorio Emanuele Ii. This commercial gallery is rated 4.7 out of 5 stars by 91,394 travelers from near and far.

Milan is also the home of La Scala. This opera house has an average rating of 4.7 out of 5 stars from 26,219 visitors.

You can continue your self-guided sightseeing tour at Sforzesco Castle Art Library. Rated 4.6 out of 5 stars by 68,714 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Parco Sempione. With an average rating of 4.6 out of 5 stars from 72,914 reviews, it’s hard to refuse the opportunity to see this park.

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

Discover a world of culinary delights in Genoa, 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 an extraordinary dining experience at The Cook, a 1-star Michelin restaurant offering an incredible modern menu. Alternatively, if your taste buds call for something different, San Giorgio is one of the best restaurants for modern, and ligurian cuisine in Genoa. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Marin. As a top-rated establishment with 1 Michelin star, it is an ideal choice for seafood, and contemporary cuisine in the city.

After your meal, keep the night alive at a bar like Scurreria Beer & Bagel, known for its lively atmosphere. La Lepre is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

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

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Day 7

Day 7 – Genoa, Pisa, and Florence

  • Florence
  • Genoa
  • Pisa
  • More

Drive 282 km, 3 hours 47 min

  • Piazza De Ferrari
  • Aquarium of Genoa
  • Leaning Tower of Pisa
  • Piazza del Duomo
  • More

Wake up to day 7 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 Genoa, and Pisa.

Begin your sightseeing with a visit to Piazza De Ferrari. This extraordinary square is rated an average of 4.6 out of 5 stars by 34,312 visitors.

Next, make your way to Aquarium Of Genoa. This top attraction is a public aquarium with an average rating of 4.5 out of 5 stars by 62,259 visitors. Aquarium Of Genoa welcomes 1,200,000 yearly visitors.

Embrace the thrill of the open road as you wave goodbye to Genoa 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 2 hours 5 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Start your sightseeing with a visit to Leaning Tower Of Pisa. This bell tower is rated an average of 4.7 out of 5 stars from 116,882 visitors. Leaning Tower Of Pisa welcomes around 3,200,000 visitors every year.

Piazza Del Duomo, Pisa is another popular attraction you could visit today. This square has a rating of 4.7 out of 5 stars from 104,550 visitors.

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.

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

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative, and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary, and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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.

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Day 8

Day 8 – Florence

  • Florence
  • More

Drive 11 km, 58 min

  • David of Michelangelo
  • Accademia Gallery
  • Cathedral of Santa Maria del Fiore
  • Piazzale Michelangelo
  • More

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.

Take the opportunity to see David. This attraction has an average rating of 4.8 out of 5 stars from 10,476 visitors.

Galleria Dell'accademia is another sightseeing hotspot in the area. This national museum has been rated an average of 4.6 out of 5 stars by 34,429 travelers. Up to 1,719,645 people visit Galleria Dell'accademia every year.

Florence is also the home of Central Market. Around 43,100 people have rated this sightseeing destination an average of 4.4 out of 5 stars.

Another place you’ll want to visit is Cathedral Of Santa Maria Del Fiore. With an average rating of 4.8 out of 5 stars from a total of 76,359 reviews, a visit to this church is a great idea.

This day of your vacation in Florence is also your chance to admire Piazzale Michelangelo. This must-visit square enjoys an average rating of 4.8 out of 5 stars from 77,744 reviews.

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

Treat yourself to a wonderful meal at Trattoria Da Burde, a top-rated dining spot in Florence. If you're in the mood for something new, try Ristorante Buca Mario, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.

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Day 9

Day 9 – Florence, and Siena

  • Siena
  • Florence
  • More

Drive 73 km, 1 hour 49 min

  • Piazza della Signoria
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • The Boboli Gardens
  • More

On day 9 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence. The day's journey will conclude in Siena, 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.

Begin your sightseeing with a visit to Piazza Della Signoria. This square is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Next up, make your way to Basilica Of Santa Croce In Florence. This church has an average rating of 4.7 out of 5 stars from 28,544 reviews.

When you’re ready for your next sight of the day, continue to Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars from 61,794 visitors. Up to 2,011,219 people visit this place of interest annually.

Beyond the above-mentioned attractions, you also have the opportunity to visit Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars by 118,099 visitors.

If you’re keen to explore even more, then consider a visit to The Boboli Gardens. This park is a much-appreciated attraction with an average rating of 4.2 out of 5 stars from 25,341 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 delicious meal at Antica Trattoria Papei, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Quattro Venti, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Siena this evening.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 10

Day 10 – Siena, Vatican City, and Rome

  • Rome
  • Siena
  • More

Drive 242 km, 3 hours 14 min

  • Piazza del Campo
  • Duomo di Siena
  • Saint Peter's Square
  • St Peter's Basilica
  • More

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

Kick off the day at Piazza Del Campo, a top pick for today’s sightseeing. This square is rated an average of 4.8 out of 5 stars in 64,175 reviews.

Today is also your chance to visit Siena Cathedral. Siena Cathedral is a domus with an average rating of 4.8 out of 5 stars from 21,656 reviews.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Vatican City, Vatican City. Your travel time is around 2 hours 45 min.

Begin your sightseeing with a visit to Saint Peter's Square. This extraordinary square is rated an average of 4.8 out of 5 stars by 38,954 visitors.

Next, make your way to St. Peter's Basilica. This top attraction is a major basilica with an average rating of 4.8 out of 5 stars by 131,043 visitors. St. Peter's Basilica welcomes 11,000,000 yearly visitors.

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 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.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean, and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative, and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean, and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Sant' Eustachio Caffè offers a unique charm perfect for experiencing the local bar scene in Rome. Caffè Portofino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 11

Day 11 – Rome

  • Rome
  • More

Drive 7 km, 57 min

  • Piazza del Popolo
  • Spanish Steps
  • Piazza di Spagna
  • Pantheon
  • Largo di Torre Argentina
  • More

Day 11 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.

Your sightseeing of the day begins at Piazza Del Popolo, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.6 out of 5 stars in 89,807 reviews.

Next, satisfy your wanderlust at Spanish Steps. This monumental staircase has an average rating of 4.5 out of 5 stars from 57,211 travelers.

Piazza Di Spagna 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 113,658 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, Largo Di Torre Argentina awaits. If you’ve been interested in experiencing a square, this is a top pick rated 4.5 out of 5 stars by 30,433 previous visitors.

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 delicious dinner at DEROMA - Farine Romane, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss Centro. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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

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Day 12

Day 12 – Rome

  • Rome
  • More

Drive 6 km, 1 hour 19 min

  • Circus Maximus
  • Colosseum
  • Roman Forum
  • Altar of the Fatherland
  • Trevi Fountain
  • More

Day 12 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.

Be one of the day’s first visitors at Circus Maximus. This circus is rated an average of 4.4 out of 5 stars by 44,741 visitors.

When you’re finished at Circus Maximus, head to Colosseum. This one-of-a-kind roman amphitheatre is rated an average of 4.7 out of 5 stars in 328,821 reviews. Every year, approximately 7,400,000 travelers come here to experience the roman amphitheatre for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Roman Forum. This square is rated an average of 4.7 out of 5 stars by 114,450 visitors.

If you’re keen to explore more, then consider a visit to Altare Della Patria. This architectural structure is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 49,843 visitors. Around 1,683,070 travelers visit Altare Della Patria every year.

To round off your sightseeing experience, make your way to Trevi Fountain. This famous sculpture is rated an average of 4.8 out of 5 stars by 343,494 travelers.

Discover a world of culinary delights in Rome, 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.

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

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 13

Day 13 – Rome

  • Rome
  • More

Drive 16 km, 1 hour 5 min

  • Villa Borghese
  • Castel Sant'Angelo
  • Piazza Navona
  • Campo de' Fiori
  • Basilica Papale di Santa Maria Maggiore
  • More

Day 13 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 Villa Borghese. This urban zone of rome is rated an average of 4.6 out of 5 stars from 69,749 visitors.

Castel Sant'angelo is another popular attraction you could visit today. This museum has a rating of 4.7 out of 5 stars from 72,431 visitors. Castel Sant'angelo attracts up to 918,591 visitors every year.

Piazza Navona is also highly recommended by travelers. This square has a rating of 4.7 out of 5 stars from 158,771 visitors.

Campo De' Fiori is an attraction you won’t want to miss. This square is rated an average of 4.4 out of 5 stars in 51,133 reviews.

Another attraction you have the opportunity to visit today is Basilica Di Santa Maria Maggiore. This major basilica has received an average rating of 4.8 out of 5 stars from 27,678 travelers.

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.

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

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 14

Day 14 – Rome, Tivoli, Teramo, and Ancona

  • Ancona
  • Tivoli
  • Teramo
  • More

Drive 317 km, 4 hours 14 min

  • Villa d'Este
  • Villa Gregoriana
  • More

Wake up to day 14 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 Tivoli, and Teramo.

Fasten your seatbelt and make your way to your next stop. Tivoli, 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 Rome to Tivoli may take around 49 min without traffic disruptions. Upon arrival in Tivoli, we highly recommend checking out some of the top attractions.

Be one of the day’s first visitors at Villa D'este. This giardino all'italiana is rated an average of 4.7 out of 5 stars by 25,000 visitors. Attracting more than 139,855 yearly visitors, it’s a top sight you don’t want to miss.

When you’re finished at Villa D'este, head to Gregorian Bridge. This one-of-a-kind point of interest is rated an average of 4.7 out of 5 stars in 199 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Villa Gregoriana. This park is rated an average of 4.7 out of 5 stars by 6,382 visitors.

When you’re ready to jump back into the car and say goodbye to Tivoli, you’ll hit the road in the direction of Teramo. This drive usually takes around 1 hour 40 min. When you arrive, enjoy some sightseeing.

Drop by the renowned Fonte Della Noce. This popular sightseeing destination has been rated an average of 4.2 out of 5 stars by 182 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.

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

Experience a harmony of flavors at Sot'Ajarchi in Ancona by securing a reservation in advance. Known for its Bib Gourmand status, Sot'Ajarchi offers a delightful variety of dishes highlighting its delicious seafood, and from the marches menu. If you're looking to mix things up, Bontà delle Marche offers an enticing alternative with its varied menu.

Following your dinner, dive into the local bar culture at Alla Tazza D'oro. Enjoy this evening's relaxed ambiance with delightful drinks.

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 15

Day 15 – Ancona - departure day

  • Ancona - Departure day
  • More
  • Piazza del Plebiscito
  • More

Today is the last day of your 15-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.

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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