Luxury 14-Day Italy Road Trip from Milan traveling south to Pisa, Florence, Rome, Arezzo, Venice, and Verona

Perfect travel plans
Everything included
Fully customizable

Description

Summary

Duration
14 days & 13 nights
Available
Jan. - Dec.
Hotel
13 nights included
Car rental
14 days included
Flights
Optional
Travel app
All vouchers, itinerary, & map

Description

Set off on the ultimate travel extravagance with this 14-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 3 nights in Milan, 1 night in Pisa, 3 nights in Florence, 3 nights in Rome, 1 night in Arezzo, 1 night in Venice, and 1 night in Verona, 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 14-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 14-day luxury self-drive holiday, including CDW insurance.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. These are only a few of the many spectacular attractions and sights you will find on your luxury travel itinerary in Italy.

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 14-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 Milan, Sarzana, Pisa, Siena, Florence, Rome, Arezzo, Bologna, Venice, and Verona 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, 13 nights
Rental car, 14 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 / 3 nights
Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, ItalyFlorence / 3 nights
Pisa - city in ItalyPisa / 1 night
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
High dynamic range (HDR) Aerial view of the city of Milan, Italy.Milan / 3 nights
Siena - city in ItalySiena
Famous buildings, gondolas and monuments by the Rialto Bridge of Venice on the Grand Canal, Italy.Venice / 1 night
Photo of aerial view of Verona historical city centre, Ponte Pietra bridge across Adige river, Verona Cathedral, Duomo di Verona, red tiled roofs, Veneto Region, Italy.Verona / 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 sunrise in san marco square with campanile and san marco's basilica. Panorama of the main square of the old town. Venice, Italy.Piazza San Marco
photo of beautiful view from the canal grande to the famous rialto bridge in Venice, Italy, without people and clear, emerald water.Rialto Bridge
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 verona, Italy. ancient amphitheater arena di verona in Italy like Rome coliseum with nighttime illumination and evening blue sky. verona's italian famous ancient landmark theatre. veneto region.Verona Arena
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
Gardaland Resort, Castelnuovo del Garda, Verona, Veneto, ItalyGardaland Resort
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 mangia tower or torre del mangia towering above of the palazzo pubblico on piazza del campo in medieval city of Siena at beautiful sunrise, tuscany, Italy.Piazza del Campo
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 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 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
photo of Night view of piazza San Marco and Doge's Palace (Palazzo Ducale) in Venice, Italy. Architecture and landmark of Venice. Night cityscape of Venice .Doge's Palace
Church of Santa Maria Novella at morning in Florence, Tuscany, ItalyBasilica di Santa Maria Novella, Firenze (FI)
photo of Beautiful view of facade and campanile of Siena Cathedral, Duomo di Siena at sunrise, Siena, Tuscany, Italy .Siena Cathedral
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 sunrise in San Marco square with Campanile and San Marco's Basilica, the main square of the old town, Venice, Veneto Italy.Saint Mark's Basilica
photo of The traditional bridge of the sighs of Barranco in Lima-PERU .Bridge of Sighs
photo of view of Verona, Italy. Scenery with Adige River and Ponte Scaligero and Castelvecchio, medieval landmarks of veronese city, Verona, Italy.Ponte Scaligero
phopto of Church of Santo Stefano dei Cavalieri in Knights Square (Piazza dei Cavalieri), Pisa, Tuscany, ItalyKnights' Square
photo of Piazza Santo Stefano .Piazza Santo Stefano
photo of Bologna, Italy. Piazza del Nettuno and Piazza Maggiore in Bologna, Italy landmark in Emilia-Romagna historical province.Fountain of Neptune, Bologna
Sarzana Cathedral Santa Maria Assunta
The facade of Palazzo Borromeo in Milan, Italy. Palazzo Borromeo

Flights
Yes
No

Round trip
Economy
Round trip
Economy

Travel details

Flights

Round trip
Economy
Round trip
Economy
Travel dates

Include flights?

Yes
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 – Milan - arrival day

  • Milan - Arrival day
  • More
  • Piazza Gae Aulenti
  • More

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

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

Before you know it, it’s time to head out for dinner. Treat yourself to a delicious meal at a nice restaurant in Milan.

Indulge in an exquisite Bib Gourmand dining experience at Enrico Bartolini al Mudec. Renowned for its prestigious 3 Michelin-star rating and an array of mouthwatering dishes, Enrico Bartolini al Mudec consistently impresses foreign and local diners, garnering praise for its exceptional creative cuisine.

As your day in Milan is coming to an end, retreat to a bar where you can celebrate the adventures and experiences you've enjoyed so far on your exciting luxury holiday in Italy. Enjoy a signature cocktail or a glass of fine wine as you toast to more adventures that await you.

When you’ve finished your meal, visit Mag Cafe for a well-deserved after-dinner drink. One of the best bars in the city, Mag Cafe has an average rating of 4.4 out of 5 stars from 3,270 customers.

If you’d rather go to a different spot, Nottingham Forest is another great option. This bar enjoys an average rating of 4.4 out of 5 stars from 2,686 bar-goers.

The Friends Pub Milano is also a great city bar with a welcoming atmosphere. The Friends Pub Milano has an average rating of 4.3 out of 5 stars from 1,689 customers.

Raise a toast to the start of your 14-day luxury vacation in Italy and look forward to more fantastic days to come!

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Experiences

Day 2

Day 2 – Milan

  • Milan
  • More

Drive 9 km, 1 hour 3 min

  • Museo della Scienza e della Tecnologia "Leonardo da Vinci"
  • Arch of Peace
  • Sempione Park
  • Sforzesco Castle Art Library
  • Pinacoteca di Brera
  • More

On day 2 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Milan. You’ll stay in Milan for 1 night, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Milan to the fullest.

This activity is one of many you can add to your luxury travel plan to make your vacation in Italy truly memorable.

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.

As your first day in Milan is coming to an end, retreat to a bar for some celebration. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

If you’re up for classic drinks with a modern flair, consider going to Kilburn Cocktail Bar Milano. Around 954 customers have given this incredible bar an average rating of 4.5 out of 5 stars.

Locals of Milan also enjoy the cocktails at BhangraBar. This place is rated an average of 4 out of 5 stars by 4,036 customers and is one of the best you can experience in the city.

Another top-rated alternative for an expertly crafted celebratory drink is Camparino in Galleria. This bar has an average rating of 4.4 out of 5 stars by 1,473 customers.

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

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Experiences

Day 3

Day 3 – Milan, Sarzana, and Pisa

  • Milan
  • Pisa
  • More

Drive 293 km, 3 hours 46 min

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano Museum
  • Sarzana Cathedral Santa Maria Assunta
  • More

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan, Sarzana, and Pisa. The day's journey will conclude in Pisa, 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.

Drop by the renowned La Scala. This popular opera house has been rated an average of 4.7 out of 5 stars by 26,219 visitors.

Another unforgettable place to experience is Galleria Vittorio Emanuele II. Rated 4.7 out of 5 stars by 91,394 visitors, this commercial gallery deserves a spot on today's sightseeing itinerary.

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

As you’ve unraveled the marvels of Milan, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Sarzana may take around 2 hours 39 min. Upon your arrival in Sarzana, you’ll be greeted with the opportunity to do some sightseeing and exploring.

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 Sarzana to Pisa may take around 53 min without traffic disruptions. Upon arrival, we highly recommend checking out some of the top attractions.

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

Check out Osteria I Santi. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.4 out of 5 stars from 3,094 reviews.

Locals also recommend Filter Coffee Lab as one of the best restaurants to have dinner at in Pisa. Filter Coffee Lab is rated an average of 4.6 out of 5 stars by 2,414 customers, including locals as well as travelers.

Alternatively, for another culinary experience you will remember, book a table at Ristorante alle Bandierine. This popular restaurant has an average rating of 4.5 out of 5 stars by 1,163 customers.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

To have one of the best bar experiences in Pisa, we recommend going to the wonderful Bar Mocambo. This bar offers a variety of phenomenal dishes and drinks and has been rated an average of 4.7 out of 5 stars by 359 customers.

If you would rather go somewhere else, check out Skyline American Bar. This is a favorite place to hang out among locals, and an excellent place to visit if you wish to make new acquaintances while enjoying a refreshing drink. Skyline American Bar has an average rating of 4.3 out of 5 stars from 510 customers.

Yet another excellent option is the popular Sud. This bar is rated an average of 4.6 out of 5 stars by 784 customers, so be sure to check out whether this is the place to celebrate tonight.

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

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Experiences

Day 4

Day 4 – Pisa, Siena, and Florence

  • Siena
  • Pisa
  • Florence
  • More

Drive 207 km, 3 hours 29 min

  • Knights' Square
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Piazza del Campo
  • Siena Cathedral
  • More

Wake up to day 4 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 3 nights. The day's itinerary unfolds with a diverse array of experiences in Pisa, Siena, and Florence.

When you're ready to see some sights, Knights' Square is a great place to start with. This square is rated an average of 4.5 out of 5 stars by 9,051 visitors.

Another popular attraction you can visit today is Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 travelers. Every year, 3,200,000 travelers come to experience this site to make the most of their time in Pisa.

We also recommend a stop at Piazza del Duomo, Pisa. The square has been rated an average of 4.7 out of 5 stars by 104,550 visitors.

Set your GPS to Siena and hit the road. Expect a journey of approximately 1 hour 54 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

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.

Continue your road trip and head to your next destination, Florence. This car ride takes around 1 hour 11 min.

While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. The best things to do, see, and eat are waiting for you.

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 top attractions in the area, 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 the city for you, so you can check out the menus and make your reservation in advance.

According to reviews, Ristorante Paoli is one of the absolute best places to eat in Florence. At this restaurant, you’ll enjoy a great atmosphere and a fantastic food and drinks menu. Ristorante Paoli is rated an average of 4.9 out of 5 stars by 6,031 customers.

Alternatively, if you’re curious to try a local favorite, check out Osteria Vecchio Cancello. This restaurant is rated an average of 4.8 out of 5 stars by 1,589 customers and guarantees you a nice dining experience to end your day.

When your taste buds call for something different, you may want to pay Ristorante Oliviero 1962 a visit instead. This restaurant is a top recommendation often mentioned by both travelers and locals. Ristorante Oliviero 1962 has an average rating of 4.7 out of 5 stars by 1,046 customers.

As the day is coming to an end, you can head back to your hotel to relax, or, go out for a drink.

Many locals go to Manifattura for an evening cocktail or glass of wine. This bar is rated an average of 4.7 out of 5 stars by 509 customers.

If you feel like going somewhere else, another popular option in the city is Caffe Concerto Paszkowski. This bar has an average rating of 4.3 out of 5 stars by 4,000 customers.

Ristorante Buca Mario is another great option in Florence, offering excellent drinks and a great atmosphere. This bar is rated an average of 4.4 out of 5 stars by 1,879 customers.

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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Experiences

Day 5

Day 5 – Florence

  • Florence
  • More

Drive 7 km, 52 min

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

On day 5 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Florence. You’ll stay in Florence for 2 nights, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Florence to the fullest.

This activity is one of many you can add to your luxury travel plan to make your vacation in Italy truly memorable.

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

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Florence.

One of the top bars in Florence is Villa Cora. This claim is supported by 699 customers who have rated it an average of 4.8 out of 5 stars.

Another great bar with an extensive drink menu is Osteria Tripperia Il Magazzino. If you ask the 951 customers who have rated it an average of 4.4 out of 5 stars, Osteria Tripperia Il Magazzino is the perfect place for a unique drinking experience.

Locals also enjoy Archea Brewery, a great place to experience the local scene and unwind during your visit. This bar has an average rating of 4.7 out of 5 stars by 723 customers.

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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Experiences

Day 6

Day 6 – Florence

  • Florence
  • More

Drive 3 km, 49 min

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

On day 6 of your exciting luxury holiday across Italy, you will continue exploring the city of Florence. You still have 1 night left in the city. Enjoy your break from the road and spend this day sightseeing and eating at some of the best restaurants in Florence. Your accommodation will be conveniently located close to several of the best attractions in the city.

This activity is one of many you can add to your luxury travel plan to make your vacation in Italy truly memorable.

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

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

Cap off the evening at Locale Firenze. This bar has an average rating of 4.6 out of 5 stars from 771 customers and is one of the best bars in Florence.

Another popular place to go for refreshing drinks and delicious bites is Cibrèo Caffè. Rated an average of 4.3 out of 5 stars by 857 customers, this spot offers customers an unforgettable bar experience.

Nab Firenze is a great bar with a rating of 4.3 out of 5 stars from 790 customers. With this impressive average rating, Nab Firenze is certainly a great place to indulge in an exquisite glass of a cold, bubbly drink.

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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Experiences

Day 7

Day 7 – Vatican City and Rome

  • Rome
  • More

Drive 283 km, 3 hours 32 min

  • Vatican Museums
  • Sistine Chapel
  • Saint Peter's Square
  • St Peter's Basilica
  • 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 Vatican City and Rome. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 3 nights at a luxury hotel in Rome adds a touch of comfort to your journey.

When you arrive, enjoy some sightseeing.

Fasten your seatbelt and make your way to your next stop. Upon arrival, we highly recommend checking out some of the top attractions.

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

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.

At the top-rated restaurant Tonnarello, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.7 out of 5 stars by 62,881 customers.

If you feel like having something else, Ristorante Pancrazio dal 1922 is another great option. This fantastic restaurant has an average rating of 4.7 out of 5 stars by 2,946 customers.

A third restaurant you could check out is Cantina e Cucina. Cantina e Cucina offers a menu of delicious dishes that are sure to satisfy your hunger. We’ll let its excellent rating of 4.6 out of 5 stars by 7,907 customers speak for itself.

After dinner, visit some of the best bars in the city of Rome. Strike up a conversation with the friendly locals to end the day perfectly.

Celebrate this wonderful day with sumptuous cocktails at RoYaL Art Cafè Roma, a terrific bar to unwind after a busy day. Around 3,972 customers rated this bar with an impressive average of 4.4 out of 5 stars.

You can continue your amazing night of celebration at Ai Tre Scalini. This bar has been rated an average of 4.4 out of 5 stars by 2,950 customers, and is an excellent place to mingle with locals and fellow travelers.

Transform your evening at Centro. This popular bar rated 4.4 out of 5 stars by 1,488 customers, offers great cocktails, good service, and a lovely atmosphere.

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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Experiences

Day 8

Day 8 – Rome

  • Rome
  • More

Drive 6 km, 1 hour 18 min

  • Trevi Fountain
  • Altare della Patria
  • Roman Forum
  • Colosseum
  • Circus Maximus
  • More

Day 8 of your luxury itinerary in Rome will be filled with memorable experiences. With magnificent attractions, delicious food, and great entertainment, you're guaranteed a lovely day in the city. Make the most out of the 2 nights you have left of your luxury holiday in Rome.

This activity is one of many you can add to your luxury travel plan to make your vacation in Italy truly memorable.

After a long day of exploring top attractions in the area, 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 the city for you, so you can check out the menus and make your reservation in advance.

As your day in Rome is coming to an end, retreat to a bar where you can celebrate the adventures and experiences you've enjoyed so far on your exciting luxury holiday in Italy. Enjoy a signature cocktail or a glass of fine wine as you toast to more adventures that await you.

Celebrate this wonderful day with sumptuous cocktails at DEROMA - Farine Romane, a terrific bar to unwind after a busy day. Around 1,432 customers rated this bar with an impressive average of 4.3 out of 5 stars.

You can continue your amazing night of celebration at Hotel Hassler Roma. This bar has been rated an average of 4.8 out of 5 stars by 895 customers, and is an excellent place to mingle with locals and fellow travelers.

Transform your evening at VinAllegro. This popular bar rated 4.3 out of 5 stars by 1,167 customers, offers great cocktails, good service, and a lovely atmosphere.

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

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Experiences

Day 9

Day 9 – Rome

  • Rome
  • More

Drive 12 km, 1 hour

  • Villa Borghese
  • Piazza del Popolo
  • Spanish Steps
  • Piazza di Spagna
  • Basilica di Santa Maria Maggiore
  • More

On day 9 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Rome. You’ll stay in Rome for 1 night, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Rome to the fullest.

This activity is one of many you can add to your luxury travel plan to make your vacation in Italy truly memorable.

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.

As your first day in Rome is coming to an end, retreat to a bar for some celebration. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

To have one of the best bar experiences in Rome, we recommend going to the wonderful Ristorante Tema. This bar offers a variety of phenomenal dishes and drinks and has been rated an average of 4.4 out of 5 stars by 939 customers.

If you would rather go somewhere else, check out La Botticella of Poggi Giovanni. This is a favorite place to hang out among locals, and an excellent place to visit if you wish to make new acquaintances while enjoying a refreshing drink. La Botticella of Poggi Giovanni has an average rating of 4.7 out of 5 stars from 655 customers.

Yet another excellent option is the popular Sant' Eustachio Caffè. This bar is rated an average of 4.2 out of 5 stars by 9,555 customers, so be sure to check out whether this is the place to celebrate tonight.

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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Experiences

Day 10

Day 10 – Rome and Arezzo

  • Rome
  • Arezzo
  • More

Drive 223 km, 3 hours 8 min

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

On day 10 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome and Arezzo. The day's journey will conclude in Arezzo, 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.

Start your day with a visit to largo di Torre Argentina. This extraordinary square is rated an average of 4.5 out of 5 stars by 30,433 visitors.

Next, make your way to Pantheon. This top attraction is a roman temple with an average rating of 4.8 out of 5 stars by 189,682 visitors. Pantheon welcomes 30,000,000 yearly visitors.

We also recommend a visit to Piazza Navona. This square is rated 4.7 out of 5 stars by 158,771 travelers.

If you’re keen to keep exploring, visit Campo de' Fiori. This highly recommended sightseeing destination has received an average rating of 4.4 out of 5 stars from 51,133 travelers.

Today is also your chance to spend some time at Castel Sant'Angelo. This museum is rated an average of 4.7 out of 5 stars by 72,431 travelers. It’s estimated that 918,591 people visit this fantastic attraction every year.

Fasten your seatbelt and make your way to your next stop. Arezzo, 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 Arezzo may take around 2 hours 23 min without traffic disruptions. Upon arrival, we highly recommend checking out some of the top attractions.

Soak in the beautiful landscapes as you drive and look forward to exploring your next destination.

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

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

At the top-rated restaurant Il Covo dei Briganti, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.7 out of 5 stars by 509 customers.

If you feel like having something else, Trattoria Il Saraceno is another great option. This fantastic restaurant has an average rating of 4.3 out of 5 stars by 1,759 customers.

A third restaurant you could check out is Antica Fonte. Antica Fonte offers a menu of delicious dishes that are sure to satisfy your hunger. We'll let its excellent rating of 4.6 out of 5 stars by 1,306 customers speak for itself.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Arezzo.

When an after-dinner drink sounds enticing, visit La Clandestina, one of the best bars in the city of Arezzo. This bar has an average rating of 4.6 out of 5 stars from 277 customers.

Get drinks as good as this day's adventure at Emilio. Considered one of the most popular bars in the city of Arezzo, this bar is rated an average of 4.6 out of 5 stars by 263 customers.

La Nuova Tagliatella is also a great bar where you can have nice chats over delicious bites. La Nuova Tagliatella has an average rating of 4.4 out of 5 stars from 275 customers.

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

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Experiences

Day 11

Day 11 – Bologna and Venice

  • Bologna
  • Venice
  • More

Drive 331 km, 3 hours 59 min

  • Fountain of Neptune, Bologna
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

Wake up to day 11 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 Venice.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Bologna. This drive usually takes around 2 hours 4 min. When you arrive, enjoy some sightseeing.

Begin your sightseeing with a visit to Fountain of Neptune, Bologna. This fountain is rated an average of 4.7 out of 5 stars in 3,952 reviews.

Next up, make your way to Piazza Maggiore. This square has an average rating of 4.7 out of 5 stars from 64,523 reviews.

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

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

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Venice. Expect your car journey to take a minimum of 1 hour 46 min. When you arrive in Venice, it's time to take a break from the road.

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

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

For a culinary experience you will remember, have a look at the menu at Ristorante La Piazza. With an average rating of 4.7 out of 5 stars by 9,892 customers, it’s truly one of the best restaurants in the whole of Venice.

If you feel like having something slightly different, check out Farini. This is one of the most recommended restaurants in the city. Considering its average rating of 4.5 out of 5 stars by 4,851 customers, it’s one that most guests enjoy.

Trattoria Bar Pontini is another restaurant you could book a table at tonight. This fantastic restaurant is often recommended by both travelers and locals in Venice, and has an impressive average rating of 4.5 out of 5 stars by 4,176 customers.

When you’ve finished your dinner at the best restaurant of your choice, and you’re in the mood for a drink, check out some of the best bars in the city.

Whether you’d like to relax with a drink or you’re in the mood for some celebration, Adagio is a great place to end your evening at. Not sure whether this is a bar worth checking out? Then the average rating of 4.9 out of 5 stars from 621 in reviews might help make your mind up.

Alternatively, check out Il Mercante, a place many locals consider their favorite in Venice. Il Mercante offers plenty of drink options for every taste and is rated an average of 4.9 out of 5 stars by 621 guests.

If you want to continue your celebrations at another bar, try Cantina Do Spade. This bar is one of the best drinking spots in Venice and is rated an average of 4.4 out of 5 stars by 3,120 customers.

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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Experiences

Day 12

Day 12 – Venice and Verona

  • Venice
  • Verona
  • More

Drive 122 km, 1 hour 39 min

  • Rialto Bridge
  • Piazza San Marco
  • Saint Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • More

Wake up to day 12 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Venice and Verona. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 1 night at a luxury hotel in Verona adds a touch of comfort to your journey.

Journey into the unknown at Rialto Bridge, a unique attraction awaiting your visit. This remarkable stone bridge has an average rating of 4.7 out of 5 stars from 141,666 reviews.

When you’re ready to continue your sightseeing, Piazza San Marco is a recommended place to visit. This square is rated an average of 4.7 out of 5 stars in 152,982 reviews.

Another must-see attraction in Venice is St Mark's Basilica. Rated an average of 4.7 out of 5 stars by 18,439 travelers, this popular tourist destination in Venice offers an experience you will remember.

Doge's Palace is another popular stop on travelers' itineraries in Venice. This palace promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 24,775 reviews. Each year, approximately 318,104 people travel to visit Doge's Palace.

Lastly, don't miss out on Bridge of Sighs. Rated 4.6 out of 5 stars by 18,223 local and international travelers, it's a popular place to visit.

Embrace the thrill of the open road as you wave goodbye to Venice and set your GPS to Verona. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 24 min. Upon reaching Verona, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. The best things to do, see, and eat are waiting for you.

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

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

Locals enjoy eating at Antica Bottega del Vino, one of the most recommended restaurants in Verona. This city restaurant has an average rating of 4.5 out of 5 stars from 2,699 customers.

If you have an appetite for something else, check out Osteria il Ciottolo. Around 2,253 customers have given this fantastic restaurant an average of 4.6 out of 5 stars.

With an average rating of 4.3 out of 5 stars from 2,370 customers, Re Teodorico is another excellent alternative that serves a whole menu of delectable dishes. Many patrons praise its unique ambiance and attentive service, making it a must-visit for both locals and tourists alike.

Verona also has several great bars that will fit every travel budget.

If you’re up for classic drinks with a modern flair, consider going to Archivio. Around 840 customers have given this incredible bar an average rating of 4.7 out of 5 stars.

Locals of Verona also enjoy the cocktails at Osteria da Ugo. This place is rated an average of 4.5 out of 5 stars by 1,724 customers and is one of the best you can experience in the city.

Another top-rated alternative for an expertly crafted celebratory drink is Signorvino. This bar has an average rating of 4.3 out of 5 stars by 1,737 customers.

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

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Experiences

Day 13

Day 13 – Verona, Ronchi, and Milan

  • Verona
  • Milan
  • More

Drive 158 km, 2 hours 31 min

  • Verona Arena
  • Ponte Scaligero
  • Gardaland Resort
  • More

On day 13 of your luxury holiday in Italy, your road trip route will take you exploring the best of Verona, Ronchi, and Milan. The day's journey will conclude in Milan, 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.

Start your sightseeing with a visit to Verona Arena. This opera house is rated an average of 4.7 out of 5 stars from 123,818 visitors. Verona Arena welcomes around 195,540 visitors every year.

Castelvecchio Bridge is another popular attraction you could visit today. This arch bridge has a rating of 4.7 out of 5 stars from 12,156 visitors.

After soaking in Verona’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Ronchi. Expect your car journey to take a minimum of 33 min. When you arrive in Ronchi, it's time to take a break from the road.

Drop by the renowned Gardaland Resort. This popular amusement park has been rated an average of 4.4 out of 5 stars by 99,291 visitors.

Milan’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Ronchi behind. This drive usually takes around 1 hour 42 min. Milan welcomes you with a multitude of unique vacation experiences.

When you arrive, enjoy some sightseeing.

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.

One of the top restaurants in the area is Bice Restaurant. This amazing restaurant offers great food meticulously prepared with the freshest ingredients. Over 579 diners have left the restaurant with an average rating of 4.3 out of 5 stars.

Another restaurant that many travelers recommend is Ribot Restaurant. Rated an average of 4.5 out of 5 stars by 3,991 customers, this restaurant is praised for its variety of dishes, warm ambiance, and amazing service.

You can also try the delicious food served at L'immagine Bistrot Ristorante for a unique dining experience. This restaurant has received approval from 2,020 tourists and locals alike, earning an average rating of 4.7 out of 5 stars in reviews.

Milan also has many fantastic bars that cater to all travel budgets.

Whether you prefer your drink shaken or stirred, Yguana Cafè is a great place to enjoy a well-deserved celebratory drink. This bar is rated an average of 4 out of 5 stars from 1,776 customers.

Alternatively, check out Rufus Cocktail Bar, a place many travelers consider their favorite in Milan. Rufus Cocktail Bar offers drinks for every taste and is rated an average of 4 out of 5 stars by 1,776 guests.

If you want to continue your night at another bar, try Tommasi Milano and soak in its inviting ambiance. This bar is one of the best drinking spots in Milan and is rated an average of 4.1 out of 5 stars in 638 reviews.

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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Experiences

Day 14

Day 14 – Milan - departure day

  • Milan - Departure day
  • More
  • Palazzo Borromeo
  • More

Today is the last day of your 14-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 Milan before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Milan’s popular marketplace. Thanks to your accommodation’s strategic location, the city’s bustling commercial district is only a stone’s throw away, giving you ample time to leisurely explore the area, filled with local shops.

Take time to find the perfect present, reminding you of the charms of Italy. Each store here is brimming with unique finds.

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

This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.4 out of 5 stars from 2,394 reviews.

Alternatively, if you’re curious to try a local favorite, check out UNAHOTELS Cusani Milano. This restaurant is rated an average of 4.3 out of 5 stars by 1,217 customers and guarantees you a nice dining experience to end your day.

If your taste buds call for something different, book a table at G. B. Bar. This popular restaurant has an average rating of 4.6 out of 5 stars by 820 customers.

You will then say farewell to Milan 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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Experiences

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