Luxury Two-Week Italy Road Trip from Ancona traveling west to Bologna, Milan, Genoa, Florence, Arezzo, and Rome

Perfect travel plans
Everything included
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Description

Summary

Duration
15 days & 14 nights
Available
Jan. - Dec.
Hotel
14 nights included
Car rental
15 days included
Flights
Economy included
Travel app
All vouchers, itinerary, & map

Description

Experience travel that redefines comfort and elegance with this 15-day luxury road trip in Italy. Witness Italy's awe-inspiring scenery, delight in the finest culinary offerings, and enjoy the ultimate comfort in top-tier accommodations.

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, 3 nights in Milan, 1 night in Genoa, 2 nights in Florence, 1 night in Arezzo, 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, Senigallia, Bologna, Milan, Genoa, Pisa, Florence, Arezzo, Rome, and Teramo at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best flights, activities, tours, and hotels in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your luxury holiday in Italy today!

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Included

Flights, economy included
Hotel, 14 nights
Rental car, 15 days
CDW Insurance
Step-by-step guide
Personal travel agent
24/7 travel support

Destinations

Arezzo - city in ItalyArezzo / 1 night
Aerial panoramic cityscape of Rome, Italy, Europe. Roma is the capital of Italy. Cityscape of Rome in summer. Rome roofs view with ancient architecture in Italy. Rome / 4 nights
Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, ItalyFlorence / 2 nights
Pisa - city in ItalyPisa
Photo of Italy Piazza Maggiore in Bologna old town tower of town hall with big clock and blue sky on background, antique buildings terracotta galleries.Bologna / 1 night
Marche - state in ItalyAncona / 2 nights
High dynamic range (HDR) Aerial view of the city of Milan, Italy.Milan / 3 nights
Teramo
Photo of beautiful landscape of panoramic aerial view port of Genoa in a summer day, Italy.Genoa / 1 night
Loreto
Senigallia

Map

Attractions

photo of trevi fountain at sunrise beautiful full view, Rome, Italy.Trevi Fountain
photo of Colosseum in Rome at sunrise, Italy, Europe.Colosseum
photo of view of Pantheon in the morning. Rome. Italy.Pantheon
photo of piazza navona in Rome, Italy. Rome navona square. Ancient stadium of Rome for athletic contests. Italy architecture and landmark. Piazza navona is one of the main attractions of Rome and Italy.Piazza navona
photo of night panoramic view of Duomo square in Milano,Italy.Duomo di Milano Museum
St. Peter's Basilica, Vatican CitySt Peter's Basilica
Vatican Museums, Vatican CityVatican Museums
photo of golden sunset over ponte vecchio bridge with traditional boat on the arno river, Florence, Italy.Ponte Vecchio
photo of medieval leaning tower of pisa (Torre di pisa) at piazza dei miracoli (Piazza del duomo), Tuscany, Italy.Leaning Tower of Pisa
photo of panoramic view of ancient ruins of a roman forum or foro romano at sunrise in rome, Italy. view from capitoline hill.Roman Forum
photo of piazza di spagna in rome, italy. Spanish steps in rome, Italy in the morning. One of the most famous squares in Rome, Italy. Rome architecture and landmark.Piazza di Spagna
photo of panorama of piazza dei miracoli with leaning tower of pisa, Italy.Piazza del Duomo, Pisa
photo of one of the world's oldest shopping malls galleria vittorio emanuele II at night in milan, lombardia, Italy.Galleria Vittorio Emanuele II
photo of piazza del popolo (People's square) named after the church of santa maria del popolo in Rome, Italy.Piazza del Popolo
photo of View of statue of david on Piazzale Michelangelo at morning  in Florence, Italy.Piazzale Michelangelo
Cathedral of Santa Maria del Fiore, Quartiere 1, Florence, Metropolitan City of Florence, Tuscany, ItalyCathedral of Santa Maria del Fiore
Sempione Park, Municipio 1, Milan, Lombardy, ItalySempione Park
photo of square of signoria in florence at sunrise, Italy.Piazza della Signoria
photo of Visit Italy, park Villa Borghese with boat and ducks.Villa Borghese
photo of holy angel castle, also known as hadrian mausoleum in the morning, Rome, Italy.Castel Sant'Angelo
photo of Sunset view of Sforza Castle (Castello Sforzesco) in Milan, Italy. Architecture and landmarks of Milan. Night cityscape of MilanSforzesco Castle Art Library
photo of bologna, Italy. Piazza maggiore with torre dell'orologio and torre dell’arengo, landmark in emilia-romagna historical province.Piazza Maggiore
photo of uffizi gallery in piazzale degli uffizi at night in florence Italy.Uffizi Gallery
PHOTO OF Old Port Porto Antico of Genoa (Genova) with yachts and boats with aquarium biosphere building under stormy sky. Genoa, ItalyAquarium of Genoa
photo of Spanish Steps at morning in Rome, Italy .Spanish Steps
Sistine ChapelSistine Chapel
photo of Campo de Fiori during the night, Rome.Campo de' Fiori
photo of altare della patria, national monument to victor emmanuel II the first king of a unified Italy, located in Rome.Altare della Patria
photo of ancient Palatine and ground of Circus Maximus on Palatine Hill in Rome, Italy.Circus Maximus
Central Market
Saint Peter's Square, R-36989Saint Peter's Square
photo of Galleria dell'Accademia in Venice, Italy.Galleria dell'Accademia
photo of Piazza De Ferrari .Piazza De Ferrari
PHOTO OF New business district Milano Porta Nuova Garibaldi (Gae Aulenti) .Piazza Gae Aulenti
photo of Largo di Torre Argentina square in Rome, Italy with four Roman Republican temples and the remains of Pompeys Theatre in the ancient Campus Martius.Largo di Torre Argentina
Basilica of Santa Croce in Florence, Quartiere 1, Florence, Metropolitan City of Florence, Tuscany, ItalyBasilica of Santa Croce in Florence
PHOTOPP OF Arco della Pace (Arch of Peace), Porta Sempione, Milan, Italy .Arch of Peace
photo of Basilica di Santa Maria Maggiore is Major papal basilica in Rome, Italy. Santa Maria Maggiore one of the most famous basilica in Rome, Italy. Architecture and landmark of Rome and Italy. Morning Rome .Basilica di Santa Maria Maggiore
photo of view of Teatro La Scala- famous opera house in Milan, Italy.La Scala
photo of view Pinacothèque de Brera - Cour intérieure, Milan,Italy.Pinacoteca di Brera
photo of Bologna, Italy - Two Towers (Due Torri), Asinelli and Garisenda, symbols of medieval Bologna towers.Two Towers
Church of Santa Maria Novella at morning in Florence, Tuscany, ItalyBasilica di Santa Maria Novella, Firenze (FI)
photo of view A picture showing the National Museum of Science and Technology of Milan, Italy.Museo della Scienza e della Tecnologia "Leonardo da Vinci"
Sanctuary of the Holy House of Loreto, Loreto, Ancona, Marche, ItalySanctuary of the Holy House of Loreto
photo of Milan, Italy panorama. View from Milan Cathedral. Royal Palace of Milan - Palazzo Realle and Velasca Tower in the background.Royal Palace of Milan
photo of view of MUDEC - Museum of Cultures, Milan, Italy.MUDEC - Museum of Cultures
PHOTO OF Santa Maria delle Grazie or Holy Mary of Grace is a church and Dominican convent in Milan, northern ItalySanta Maria delle Grazie Church
Basilica di Sant'Ambrogio, Municipio 1, Milan, Lombardy, ItalyBasilica di Sant'Ambrogio
Piazza Duomo, Municipio 1, Milan, Lombardy, ItalyCathedral Square
Rocca Roveresca, Senigallia, Ancona, Marche, ItalyRocca Roveresca
photo of Bologna, Italy. Piazza del Nettuno and Piazza Maggiore in Bologna, Italy landmark in Emilia-Romagna historical province.Fountain of Neptune, Bologna
photo of view Bologna aerial cityscape view with cathedral and old medieval city center with Altabella and Uguzzoni Towers, Bologna, Italy.Bologna Cathedral
Plebiscito square (or Pope square) with San Domenico Church in Ancona. Marche Region, Italy.Piazza del Plebiscito
PHOTO OF Bologna, Italy. Fontana del Nettuno, Palazzo Re Enzo in Piazza Maggiore, Italy landmark in Emilia-Romagna historical province.Palazzo Re Enzo
Parco Della Cittadella di Ancona, Ancona, Marche, ItalyParco Della Cittadella di Ancona
Santuario Madonna Delle Grazie
Roman Theatre of Teramo, Teramo, Abruzzo, ItalyRoman Theatre of Teramo

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Economy
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Day 1

Day 1 – Ancona - arrival day

  • Ancona - Arrival day
  • More
  • Piazza del Plebiscito
  • 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!

Start your sightseeing with a visit to piazza del Plebiscito. This square is rated an average of 4.4 out of 5 stars from 2,631 visitors.

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

After 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 Ancona for you so you can browse their menus in advance and make a reservation.

Experience a taste of Sot'Ajarchi in Ancona by booking a reservation in advance. Renowned for its Bib Gourmand distinction, Sot'Ajarchi delights its guests with its exceptional variety of meals showcasing delicious seafood, and from the marches cuisine.

Keep the excitement of the evening going by going to a bar or two. Posa bar is an excellent place to start. You could also check out bar four roses, offering a different kind of charm. A last recommendation for the day is Amarillo Beer Bar Ancona. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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, Senigallia, and Bologna

  • Bologna
  • Loreto
  • Senigallia
  • More

Drive 278 km, 3 hours 28 min

  • Sanctuary of the Holy House of Loreto
  • Rocca Roveresca
  • 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 Loreto, and Senigallia. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

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 31 min.

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Senigallia. This drive usually takes around 41 min, without any stops or traffic disruptions.

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

Continue your journey at Piazza Garibaldi. This point of interest is rated 4.4 out of 5 stars by 1,563 travelers from near and far.

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

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

Get ready for an unforgettable culinary journey in Bologna by reserving a table at I Portici. Renowned as a 1-star Michelin restaurant, it offers an exceptional creative, and contemporary menu. For a different taste experience, head to Ahimè, recognized for its delicious country cooking dishes. This Bib Gourmand restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Trattoria di Via Serra, a local favorite known for its delightful emilian cuisine in Bologna. Nestled in the heart of the city, this Bib Gourmand awardee is an ideal choice for discerning emilian foodies seeking culinary excellence.

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.

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

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Day 3

Day 3 – Bologna, and Milan

  • Milan
  • Bologna
  • More

Drive 214 km, 2 hours 41 min

  • Bologna Cathedral
  • Two Towers
  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
  • 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 Milan, where you'll be staying for 3 nights. The day's itinerary unfolds with a diverse array of experiences in Bologna.

Your sightseeing of the day begins at Bologna Cathedral, a remarkable catholic cathedral where it’s easy to get lost in exploration. This top attraction is rated an average of 4.6 out of 5 stars in 3,852 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.

Beyond the above-mentioned sites, you also have the opportunity to visit Fountain of Neptune, Bologna. This well-loved fountain boasts a 4.7 out of 5-star rating from 3,952 reviews.

When there’s still energy left for exploring, Palazzo Re Enzo awaits. If you’ve been interested in experiencing a palazzo, this is a top pick rated 4.6 out of 5 stars by 2,072 previous visitors.

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

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

Start 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 your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/Bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun evening.

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

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Day 4

Day 4 – Milan

  • Milan
  • More

Drive 1 km, 21 min

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano Museum
  • Cathedral Square
  • Royal Palace of Milan
  • More

Day 4 of your luxury road trip in Italy begins and concludes in the city of Milan. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Milan, where you still have 2 nights nights remaining.

A top pick for your self-guided sightseeing tour today is La Scala. Previous visitors have rated this opera house an average of 4.7 out of 5 stars in 26,219 reviews.

Galleria Vittorio Emanuele II is a local recommendation that you also can pay a visit today. This commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

Another attraction you won't want to miss is Duomo di Milano Museum. This art museum is rated an average of 4.8 out of 5 stars in 138,554 reviews. Every year, around 341,609 travelers visit this site to discover its unique features.

Cathedral Square is another outstanding experience in Milan. Around 7,539 travelers have rated this sightseeing destination an average of 4.8 out of 5 stars.

If you long for more, Royal Palace of Milan is not far away. This art museum is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.6 out of 5 stars in 17,538 reviews.

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.

If you’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano is another excellent spot to enjoy a nightcap after a delightful meal.

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

  • Milan
  • More

Drive 8 km, 1 hour 7 min

  • Piazza Gae Aulenti
  • Pinacoteca di Brera
  • Sforzesco Castle Art Library
  • Sempione Park
  • Arch of Peace
  • More

Day 5 of your luxury road trip in Italy begins and concludes in the city of Milan. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Milan, where you still have 1 night nights remaining.

An excellent attraction to start your day with is Piazza Gae Aulenti. This square is rated an average of 4.6 out of 5 stars in 30,398 reviews.

Continue your journey at Pinacoteca di Brera. This art museum is rated 4.7 out of 5 stars by 26,077 travelers from near and far. Approximately 417 people come to this place of interest every year to enjoy a unique experience in Milan.

Milan is also the home of Sforzesco Castle Art Library. This library has an average rating of 4.6 out of 5 stars from 68,714 visitors.

You can continue your self-guided sightseeing tour at Parco Sempione. Rated 4.6 out of 5 stars by 72,914 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Arch of Peace. With an average rating of 4.6 out of 5 stars from 27,502 reviews, it’s hard to refuse the opportunity to see this monument.

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

Cap off your dinner by heading to BhangraBar, ideal for a leisurely evening with a drink in hand. Rufus Cocktail Bar is another bar that offers an enjoyable setting. Similarly, Ostello Bello Grande 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 6

Day 6 – Milan, and Genoa

  • Genoa
  • Milan
  • More

Drive 149 km, 2 hours 34 min

  • Basilica di Sant'Ambrogio
  • Museo della Scienza e della Tecnologia "Leonardo da Vinci"
  • Santa Maria delle Grazie Church
  • MUDEC - Museum of Cultures
  • More

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

When you're ready to see some sights, Basilica di Sant'Ambrogio is a great place to start. This church is rated an average of 4.7 out of 5 stars by 12,883 visitors.

Another popular attraction you can visit today is Museo della Scienza e della Tecnologia "Leonardo da Vinci". This technology museum has an average rating of 4.5 out of 5 stars from 22,235 travelers. Every year, 532,084 travelers come to experience this site to make the most of their time in Milan.

We also recommend a stop at Santa Maria delle Grazie Church. The convent has been rated an average of 4.5 out of 5 stars by 13,490 visitors.

If you're keen to explore more, consider visiting MUDEC - Museum of Cultures. This ethnographic museum is a popular attraction with an average rating of 4.4 out of 5 stars from 14,355 reviews. As a top-rated attraction, it's no surprise that 626,650 people visit MUDEC - Museum of Cultures every year.

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

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

Discover the culinary delights of Genoa by securing a reservation at The Cook. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of modern cuisine. For an alternative dining experience, try San Giorgio, renowned for its delicious modern, and ligurian dishes. This esteemed 1-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Marin, a highly recommended local eatery celebrated for its mouthwatering seafood, and contemporary menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Keep the evening going at Scurreria Beer & Bagel, a great choice for enjoying the after-dinner hours with a drink. You could also go to La Lepre, which offers a similarly pleasant setting and great drinks.

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 7

Day 7 – Genoa, Pisa, and Florence

  • Florence
  • Genoa
  • Pisa
  • More

Drive 268 km, 3 hours 48 min

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

Wake up to day 7 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Genoa, and Pisa. 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 piazza De Ferrari. This square is rated an average of 4.6 out of 5 stars in 34,312 reviews.

Continue your journey at Aquarium of Genoa. This public aquarium is rated 4.5 out of 5 stars by 62,259 travelers from near and far. Approximately 1,200,000 people come to this place of interest every year to enjoy a unique experience in Genoa.

When you’re ready to jump back into the car and say goodbye to Genoa, you’ll hit the road in the direction of Pisa. This drive usually takes around 2 hours 3 min. When you arrive, enjoy some sightseeing.

Take the opportunity to see Piazza del Duomo, Pisa. This attraction has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Leaning Tower of Pisa is another sightseeing hotspot in the area. This bell tower has been rated an average of 4.7 out of 5 stars by 116,882 travelers. Up to 3,200,000 people visit Leaning Tower of Pisa every year.

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 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.

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative, and mediterranean 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 Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary, and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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.

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 8

Day 8 – Florence

  • Florence
  • More

Drive 4 km, 1 hour 5 min

  • Piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • 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.

Journey into the unknown at piazzale Michelangelo, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.8 out of 5 stars from 77,744 reviews.

When you’re ready to continue your sightseeing, Basilica of Santa Croce in Florence is a recommended place to visit. This church is rated an average of 4.7 out of 5 stars in 28,544 reviews.

Another must-see attraction in Florence is piazza della Signoria. Rated an average of 4.8 out of 5 stars by 66,956 travelers, this popular tourist destination in Florence offers an experience you will remember.

Uffizi Gallery is another popular stop on travelers' itineraries in Florence. This national museum promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 61,794 reviews. Each year, approximately 2,011,219 people travel to visit Uffizi Gallery.

Lastly, don't miss out on Ponte Vecchio. Rated 4.7 out of 5 stars by 118,099 local and international travelers, it's a popular place to visit.

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

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 9

Day 9 – Florence, and Arezzo

  • Arezzo
  • Florence
  • More

Drive 79 km, 1 hour 35 min

  • Cathedral of Santa Maria del Fiore
  • Basilica di Santa Maria Novella, Firenze (FI)
  • Central Market
  • Galleria dell'Accademia
  • More

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

Make Cathedral of Santa Maria del Fiore your first stop of the day. Previous visitors have rated this church an average of 4.8 out of 5 stars in 76,359 reviews.

Next up, make a stop at Basilica di Santa Maria Novella, Firenze (FI). With an average rating of 4.7 out of 5 stars by 23,075 visitors, it's easy to understand why so many people visit this archives every year.

Central Market is another attraction you can visit on this day of your vacation. This point of interest has an average rating of 4.4 out of 5 stars by 43,100 visitors.

When you’re finished at Central Market, the perfect next stop is Galleria dell'Accademia. This national museum is rated an average of 4.6 out of 5 stars in 34,429 reviews. Galleria dell'Accademia attracts approximately 1,719,645 visitors annually.

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

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

Experience a symphony of flavors at Octavin in Arezzo by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Octavin delights its guests with its exceptional variety of meals showcasing delicious creative cuisine.

To truly maximize your evening out, consider visiting Liquid Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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 10

Day 10 – Arezzo, Vatican City, and Rome

  • Rome
  • More

Drive 227 km, 2 hours 52 min

  • Vatican Museums
  • Sistine Chapel
  • Saint Peter's Square
  • St Peter's Basilica
  • More

On day 10 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. 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, Vatican City.

Be one of the day’s first visitors at Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Attracting more than 1,612,530 yearly visitors, it’s a top sight you don’t want to miss.

When you’re finished at Vatican Museums, head to Sistine Chapel. This one-of-a-kind chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Saint Peter's Square. This square is rated an average of 4.8 out of 5 stars by 38,954 visitors.

If you’re keen to explore more, then consider a visit to St. Peter's Basilica. This major basilica is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 131,043 visitors. Around 11,000,000 travelers 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.

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.

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean, and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative, and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean, and creative menu.

Round off your dining experience by visiting La Botticella of Poggi Giovanni, a prime location for a drink. Alternatively, explore the distinctive characteristics of Sant' Eustachio Caffè, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 11

Day 11 – Rome

  • Rome
  • More

Drive 7 km, 1 hour 3 min

  • Spanish Steps
  • Piazza di Spagna
  • Trevi Fountain
  • Roman Forum
  • Colosseum
  • 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.

Begin your sightseeing with a visit to Spanish Steps. This monumental staircase is rated an average of 4.5 out of 5 stars in 57,211 reviews.

Next up, make your way to Piazza di Spagna. This square has an average rating of 4.7 out of 5 stars from 113,658 reviews.

When you’re ready for your next sight of the day, continue to Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars from 343,494 visitors.

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 even more, then consider a visit to Colosseum. This roman amphitheatre is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 328,821 visitors. Approximately 7,400,000 travelers visit Colosseum every year.

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

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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 12

Day 12 – Rome

  • Rome
  • More

Drive 7 km, 55 min

  • Largo di Torre Argentina
  • Pantheon
  • Piazza navona
  • Campo de' Fiori
  • Castel Sant'Angelo
  • 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.

Kick off the day at largo di Torre Argentina, a top pick for today’s sightseeing. This square is rated an average of 4.5 out of 5 stars in 30,433 reviews.

Today is also your chance to visit Pantheon. Pantheon is a roman temple with an average rating of 4.8 out of 5 stars from 189,682 reviews. Attracting more than 30,000,000 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

Piazza Navona is another top attraction we highly recommend you visit today. This square is rated an average of 4.7 out of 5 stars by 158,771 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Campo de' Fiori. This square is rated an average of 4.4 out of 5 stars by 51,133 visitors.

Lastly, don’t miss out on Castel Sant'Angelo, a famous museum in Rome. This attraction welcomes 918,591 visitors annually and is rated an average of 4.7 out of 5 stars by 72,431 travelers.

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.

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

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Day 13

Day 13 – Rome

  • Rome
  • More

Drive 12 km, 55 min

  • Piazza del Popolo
  • Villa Borghese
  • Basilica di Santa Maria Maggiore
  • Circus Maximus
  • Altare della Patria
  • 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.

Be one of the day’s first visitors at piazza del Popolo. This square is rated an average of 4.6 out of 5 stars by 89,807 visitors.

When you’re finished at piazza del Popolo, head to Villa Borghese. This one-of-a-kind urban zone of rome is rated an average of 4.6 out of 5 stars in 69,749 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Basilica di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars by 27,678 visitors.

If you’re keen to explore more, then consider a visit to Circus Maximus. This circus is a much-appreciated attraction with an average rating of 4.4 out of 5 stars from 44,741 visitors.

To round off your sightseeing experience, make your way to Altare della Patria. This famous architectural structure welcomes around 1,683,070 visitors annually and is rated an average of 4.8 out of 5 stars by 49,843 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.

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 14

Day 14 – Rome, Teramo, and Ancona

  • Ancona
  • Teramo
  • More

Drive 311 km, 3 hours 53 min

  • Santuario Madonna Delle Grazie
  • Roman Theatre of Teramo
  • More

Wake up to day 14 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Teramo. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Teramo. 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 7 min. Upon reaching Teramo, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

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

Next up, make your way to Roman Theatre of Teramo. This sightseeing destination has an average rating of 4.2 out of 5 stars from 129 reviews.

When you’re ready for your next sight of the day, continue to Fontana dei Due Leoni. This park has an average rating of 4.6 out of 5 stars from 118 visitors.

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

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Alla Tazza D'Oro stands out as an excellent choice for a post-dinner cocktail.

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

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Day 15

Day 15 – Ancona - departure day

  • Ancona - Departure day
  • More
  • Parco Della Cittadella di Ancona
  • 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.

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 Parco Della Cittadella di Ancona. This extraordinary park and attraction is rated an average of 4.4 out of 5 stars in 843 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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