Luxury Two-Week Italy Road Trip from Pisa to Genoa, Milan, Bologna, Arezzo, Rome, and Florence and surrounding area

Perfect travel plans
Everything included
Fully customizable

Description

Summary

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

Description

Escape for the holiday of a lifetime with this 15-day luxury road trip in Italy!

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned vacation itinerary, you will stay 2 nights in Pisa, 1 night in Genoa, 3 nights in Milan, 1 night in Bologna, 1 night in Arezzo, 4 nights in Rome, and 2 nights in Florence, 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 Pisa, Genoa, Milan, Bologna, Arezzo, Rome, and Florence 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

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 / 2 nights
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
High dynamic range (HDR) Aerial view of the city of Milan, Italy.Milan / 3 nights
Photo of beautiful landscape of panoramic aerial view port of Genoa in a summer day, Italy.Genoa / 1 night

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
Foro Italico
Church of Santa Maria Novella at morning in Florence, Tuscany, ItalyBasilica di Santa Maria Novella, Firenze (FI)
photo of view of Archbasilica of St.John Lateran, San Giovanni in Laterano in Rome, the official ecclesiastical seat of the Bishop of Rome, Italy.Archbasilica of St John Lateran
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"
photo of view of Capitoline Hill (Campidoglio) is one of the Seven Hills of Rome, Italy. Rome architecture and landmark. Capitolium is one of the attractions of Rome, Italy.Capitoline Hill
Auditorium Parco della Musica
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 viewOrange Garden, Rome, Italy.Orange Garden
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
Parco Regionale Migliarino, San Rossore, Massaciuccoli, Pisa, Tuscany, ItalyParco Regionale Migliarino, San Rossore, Massaciuccoli
photo of view of Genoa Cathedral of Saint Lawrence - Italy.Genoa Cathedral
phopto of Church of Santo Stefano dei Cavalieri in Knights Square (Piazza dei Cavalieri), Pisa, Tuscany, ItalyKnights' Square
photo of Tower and cathedral, famous landmarks of Pisa, Italy .Cattedrale di Pisa
Piazza Duomo, Municipio 1, Milan, Lombardy, ItalyCathedral Square
Doge's Palace, Centro Est, Genoa, Liguria, ItalyDoge's Palace
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
PHOTO OF Bologna, Italy. Fontana del Nettuno, Palazzo Re Enzo in Piazza Maggiore, Italy landmark in Emilia-Romagna historical province.Palazzo Re Enzo
photo of Palazzo Gambacorti .Palazzo Gambacorti
Angelo Caduto, Pisa, Tuscany, ItalyAngelo Caduto

Flights
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No

Round trip
Economy
Round trip
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Travel details

Flights

Round trip
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Travel dates

Include flights?

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No

Travelers

Rooms

Flights

Car
Yes
No

Car

Small car

Small car

Category
small car
Transmission
People
Large bags
Medium car

Medium car

Category
Medium
Transmission
People
Large bags
Premium car

Premium car

Category
premium car
Transmission
People
Large bags

Hotels

Personalize your itinerary

Day 1

Day 1 – Pisa - arrival day

  • Pisa - Arrival day
  • More
  • Knights' Square
  • More

Your luxury holiday in Italy begins as soon as you reach the city of Pisa. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

A top pick for your self-guided sightseeing tour today is Knights' Square. Previous visitors have rated this square an average of 4.5 out of 5 stars in 9,051 reviews.

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

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

Round off your dining experience by visiting JEFFER cocktails & friends, a prime location for a drink. Alternatively, explore the distinctive characteristics of Le Parisien Wine Bar, a bar catering to every mood and preference. Las Volta cocktailbar likewise offers a unique atmosphere, perfect for 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 – Pisa, Cascine Vecchie, and Genoa

  • Genoa
  • Pisa
  • More

Drive 171 km, 2 hours 29 min

  • Leaning Tower of Pisa
  • Angelo Caduto
  • Piazza del Duomo, Pisa
  • Cattedrale di Pisa
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
  • 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 Pisa and Cascine Vecchie. 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 Pisa and set your GPS to Genoa. 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. Upon reaching Genoa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Be one of the day’s first visitors at Leaning Tower of Pisa. This bell tower is rated an average of 4.7 out of 5 stars by 116,882 visitors. Attracting more than 3,200,000 yearly visitors, it’s a top sight you don’t want to miss.

When you’re finished at Leaning Tower of Pisa, head to Angelo Caduto. This one-of-a-kind point of interest is rated an average of 4.5 out of 5 stars in 150 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza del Duomo, Pisa. This square is rated an average of 4.7 out of 5 stars by 104,550 visitors.

If you’re keen to explore more, then consider a visit to Pisa Cathedral. This cathedral is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 8,361 visitors.

Set your GPS to Cascine Vecchie and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cascine Vecchie beckons with new experiences!

Start your sightseeing with a visit to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This park is a popular stop on travelers’ itineraries in Cascine Vecchie, with an average rating of 4.4 out of 5 stars by 9,632 visitors.

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

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.

Discover the culinary delights of Genoa by securing a reservation at The Cook. Esteemed for its , 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.

If you’re not ready to end the night just yet, Scurreria Beer & Bagel offers a perfect venue to relax and savor a drink. Similarly, La Lepre is well-suited for those looking to unwind in a social setting.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

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Day 3

Day 3 – Genoa and Milan

  • Milan
  • Genoa
  • More

Drive 141 km, 2 hours 10 min

  • Piazza De Ferrari
  • Doge's Palace
  • Genoa Cathedral
  • Aquarium of Genoa
  • 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 Genoa.

Continue your road trip and head to your next destination, Milan. This car ride takes around 1 hour 58 min.

A top pick for your self-guided sightseeing tour today is piazza De Ferrari. Previous visitors have rated this square an average of 4.6 out of 5 stars in 34,312 reviews.

Doge's Palace is a local recommendation that you also can pay a visit today. This museum is rated an average of 4.6 out of 5 stars in 7,612 reviews.

Another attraction you won't want to miss is Genoa Cathedral. This cathedral is rated an average of 4.6 out of 5 stars in 8,971 reviews.

Aquarium of Genoa is another outstanding experience in Genoa. Around 62,259 travelers have rated this public aquarium an average of 4.5 out of 5 stars. The attraction hosts 1,200,000 visitors annually.

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

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

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds , 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, 20 min

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

Seize the day by visiting some of the best attractions in the area, like Royal Palace of Milan. This extraordinary art museum has an average rating of 4.6 out of 5 stars from 17,538 visitors.

Next, make your way to Cathedral Square. This sightseeing destination is rated an average of 4.8 out of 5 stars in 7,539 reviews.

While in Milan, we also recommend a visit to Duomo di Milano Museum. Hosting around 341,609 visitors every year, Duomo di Milano Museum is one of the best places to visit. This art museum has been rated an average of 4.8 out of 5 stars in 138,554 reviews.

If you’re keen to explore even more, then consider a visit to Galleria Vittorio Emanuele II. With an average rating of 4.7 out of 5 stars by 91,394 travelers, this commercial gallery is a highly recommended stop on your sightseeing around Milan.

Make your way to La Scala, perhaps the most famous opera house in Milan. This attraction is rated an average of 4.7 out of 5 stars in 26,219 reviews.

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.

After savoring a delicious meal, step into the vibrant nightlife at Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day 5

Day 5 – Milan

  • Milan
  • More

Drive 15 km, 1 hour 5 min

  • Piazza Gae Aulenti
  • Arch of Peace
  • Sempione Park
  • Sforzesco Castle Art Library
  • MUDEC - Museum of Cultures
  • 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.

Take the opportunity to see Piazza Gae Aulenti. This attraction has an average rating of 4.6 out of 5 stars from 30,398 visitors.

Arch of Peace is another sightseeing hotspot in the area. This monument has been rated an average of 4.6 out of 5 stars by 27,502 travelers.

Milan is also the home of Parco Sempione. Around 72,914 people have rated this park an average of 4.6 out of 5 stars.

Another place you’ll want to visit is Sforzesco Castle Art Library. With an average rating of 4.6 out of 5 stars from a total of 68,714 reviews, a visit to this library is a great idea.

This day of your vacation in Milan is also your chance to admire MUDEC - Museum of Cultures. This must-visit ethnographic museum enjoys an average rating of 4.4 out of 5 stars from 14,355 reviews. Approximately 626,650 people travel to Milan every year to see this attraction with their own eyes.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at BhangraBar, a well-loved spot among locals and tourists. Or, head to Rufus Cocktail Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ostello Bello Grande, another top-rated place in the area.

Reminisce about your day, look through photos, and prepare for another great day to come! Your luxury holiday in Italy has plenty more in store for you.

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Day 6

Day 6 – Milan and Bologna

  • Bologna
  • Milan
  • More

Drive 218 km, 3 hours 18 min

  • Pinacoteca di Brera
  • Santa Maria delle Grazie Church
  • Museo della Scienza e della Tecnologia "Leonardo da Vinci"
  • Basilica di Sant'Ambrogio
  • 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.

Bologna’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Milan behind. This drive usually takes around 2 hours 37 min. Bologna welcomes you with a multitude of unique vacation experiences.

Take the opportunity to see Pinacoteca di Brera. This attraction has an average rating of 4.7 out of 5 stars from 26,077 visitors and gets around 417 visits every year.

Santa Maria delle Grazie Church is another sightseeing hotspot in the area. This convent has been rated an average of 4.5 out of 5 stars by 13,490 travelers.

Milan is also the home of Museo della Scienza e della Tecnologia "Leonardo da Vinci". This technology museum gets more than 532,084 visitors on an annual basis. Around 22,235 people have rated this technology museum an average of 4.5 out of 5 stars.

Another place you’ll want to visit is Basilica di Sant'Ambrogio. With an average rating of 4.7 out of 5 stars from a total of 12,883 reviews, a visit to this church is a great idea.

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

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

Treat yourself to an extraordinary dining experience at I Portici, a 1-star Michelin restaurant offering an incredible creative and contemporary menu. Alternatively, if your taste buds call for something different, Ahimè is one of the best restaurants for country cooking cuisine in Bologna. This Bib Gourmand-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated Bib Gourmand-establishment, it is an ideal choice for emilian cuisine in the city.

After enjoying a fulfilling meal, continue your evening at Bar Freud e Squisito, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Osteria del Sole offers a welcoming atmosphere for easing into the nightlife. Similarly, Macondo - Cocktail Bar provides an excellent environment for a relaxed and enjoyable evening.

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 – Bologna and Arezzo

  • Arezzo
  • Bologna
  • More

Drive 181 km, 2 hours 26 min

  • Bologna Cathedral
  • Two Towers
  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
  • 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 Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

As you’ve unraveled the marvels of Bologna, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Arezzo may take around 2 hours 10 min. Upon your arrival in Arezzo, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make Bologna Cathedral one of your first sightseeing stops in Bologna. Rated an average of 4.6 out of 5 stars by 3,852 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 Maggiore. This square has been rated an average of 4.7 out of 5 stars by 64,523 visitors.

If you’re keen to explore more, head to Fountain of Neptune, Bologna. A trip to this popular fountain is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 3,952 previous visitors.

Another top place to visit is Palazzo Re Enzo. This palazzo enjoys an average rating of 4.6 out of 5 stars from 2,072 local and international travelers.

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

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

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu.

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

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 – 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

Wake up to day 8 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.

Set your GPS to Vatican City and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Vatican City beckons with new experiences!

Start your sightseeing with a visit to Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars from 133,310 visitors. Vatican Museums welcomes around 1,612,530 visitors every year.

Sistine Chapel is another popular attraction you could visit today. This chapel has a rating of 4.7 out of 5 stars from 52,083 visitors.

Saint Peter's Square is also highly recommended by travelers. This square has a rating of 4.8 out of 5 stars from 38,954 visitors.

St. Peter's Basilica is an attraction you won’t want to miss. Around 11,000,000 people visit this place every year. This major basilica is rated an average of 4.8 out of 5 stars in 131,043 reviews.

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

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

Experience a taste of local culinary excellence while in Rome by securing a table at La Pergola. Esteemed as a 3-star Michelin restaurant, it features an exceptional mediterranean and contemporary menu. For an alternative taste experience, visit Il Pagliaccio, famous for its scrumptious creative and innovative dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Enoteca La Torre, a local favorite celebrated for its exquisite mediterranean and creative cuisine in Rome. Located in the heart of the city, this 2-star Michelin restaurant is an ideal pick for mediterranean and creative cuisine lovers seeking top-notch culinary experiences.

Keep the evening going at La Botticella of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Sant' Eustachio Caffè, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

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 – Rome

  • Rome
  • More

Drive 11 km, 1 hour 2 min

  • Spanish Steps
  • Piazza di Spagna
  • Trevi Fountain
  • Pantheon
  • Castel Sant'Angelo
  • More

Day 9 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.

A top pick for your self-guided sightseeing tour today is Spanish Steps. Previous visitors have rated this monumental staircase an average of 4.5 out of 5 stars in 57,211 reviews.

Piazza di Spagna 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 113,658 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.

Pantheon is another outstanding experience in Rome. Around 189,682 travelers have rated this roman temple an average of 4.8 out of 5 stars. The attraction hosts 30,000,000 visitors annually.

If you long for more, Castel Sant'Angelo is not far away. This museum is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.7 out of 5 stars in 72,431 reviews.

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

Esteemed as a restaurant, it features an exceptional menu.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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 10

Day 10 – Rome

  • Rome
  • More

Drive 6 km, 59 min

  • Archbasilica of St John Lateran
  • Colosseum
  • Roman Forum
  • Capitoline Hill
  • Altare della Patria
  • More

Day 10 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 2 nights nights remaining.

An excellent attraction to start your day with is Archbasilica of St. John Lateran. This catholic cathedral is rated an average of 4.8 out of 5 stars in 21,370 reviews.

Continue your journey at Colosseum. This roman amphitheatre is rated 4.7 out of 5 stars by 328,821 travelers from near and far. Approximately 7,400,000 people come to this place of interest every year to enjoy a unique experience in Rome.

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

You can continue your self-guided sightseeing tour at Capitoline Hill. Rated 4.7 out of 5 stars by 19,557 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Altare della Patria. With an average rating of 4.8 out of 5 stars from 49,843 reviews, it’s hard to refuse the opportunity to see this architectural structure. Approximately 1,683,070 people visit this attraction every year.

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.

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 11

Day 11 – Rome

  • Rome
  • More

Drive 13 km, 1 hour 3 min

  • Piazza del Popolo
  • Villa Borghese
  • Basilica di Santa Maria Maggiore
  • Circus Maximus
  • Orange Garden
  • 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 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 Orange Garden. This famous park is rated an average of 4.7 out of 5 stars by 17,939 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.

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 12

Day 12 – Rome and Florence

  • Florence
  • Rome
  • More

Drive 282 km, 4 hours 5 min

  • Largo di Torre Argentina
  • Campo de' Fiori
  • Piazza navona
  • Auditorium Parco della Musica
  • Foro Italico
  • More

On day 12 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome. 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 Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Florence. Expect your car journey to take a minimum of 2 hours 58 min. When you arrive in Florence, it's time to take a break from the road.

When you’re ready for some sightseeing, make your way to largo di Torre Argentina. This much-appreciated square is rated 4.5 out of 5 stars in 30,433 reviews.

Next up is Campo de' Fiori. This square has an average rating of 4.4 out of 5 stars from 51,133 visitors.

Another top sightseeing recommendation is Piazza Navona. This square has been rated 4.7 out of 5 stars in 158,771 reviews.

Auditorium Parco della Musica is another attraction you have the opportunity to visit today. This point of interest has an average rating of 4.6 out of 5 stars from 19,687 reviews.

To continue your sightseeing, head over to Foro Italico. This sightseeing destination is rated an average of 4.6 out of 5 stars in 25,438 reviews.

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

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

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant 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.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, SE·STO on Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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 13

Day 13 – 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 13 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.

Begin your sightseeing with a visit to piazzale Michelangelo. This square is rated an average of 4.8 out of 5 stars in 77,744 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 piazza della Signoria. This square has an average rating of 4.8 out of 5 stars from 66,956 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Uffizi Gallery. This national museum is rated an average of 4.7 out of 5 stars by 61,794 visitors. Visiting Uffizi Gallery means you'll be one of 2,011,219 people who do so every year.

If you’re keen to explore even more, then consider a visit to Ponte Vecchio. This deck arch bridge is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 118,099 visitors.

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.

As a top-rated it is an ideal choice in the city.

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

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Day 14

Day 14 – Florence and Pisa

  • Pisa
  • Florence
  • More

Drive 83 km, 1 hour 38 min

  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • Central Market
  • Basilica di Santa Maria Novella, Firenze (FI)
  • 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 Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Fasten your seatbelt and make your way to your next stop. Pisa, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Florence to Pisa may take around 1 hour 8 min without traffic disruptions. Upon arrival in Pisa, we highly recommend checking out some of the top attractions.

When you're ready to see some sights, Cathedral of Santa Maria del Fiore is a great place to start. This church is rated an average of 4.8 out of 5 stars by 76,359 visitors.

Another popular attraction you can visit today is Galleria dell'Accademia. This national museum has an average rating of 4.6 out of 5 stars from 34,429 travelers. Every year, 1,719,645 travelers come to experience this site to make the most of their time in Florence.

We also recommend a stop at Central Market. The sightseeing destination has been rated an average of 4.4 out of 5 stars by 43,100 visitors.

If you're keen to explore more, consider visiting Basilica di Santa Maria Novella, Firenze (FI). This archives is a popular attraction with an average rating of 4.7 out of 5 stars from 23,075 reviews.

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

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

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

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

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Day 15

Day 15 – Pisa - departure day

  • Pisa - Departure day
  • More
  • Palazzo Gambacorti
  • 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 Pisa before saying goodbye.

As your final day in Italy unfolds, don’t miss the chance for a last-minute shopping spree in Pisa’s best shopping location. 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 Pisa one last time before you head to the airport.

Dine in style at Sud, a top recommendation for dinner tonight. Or, for a change of pace, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Boasts a menu that's sure to impress.

You will then say farewell to Pisa 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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