Luxury 10-Day Italy Road Trip Vacation from Milan traveling east to Florence, Rome, and Arezzo

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!

The first destination of your luxury vacation in Italy is Milan - a city with many fantastic attractions to explore. Catch an early flight to enjoy as much time as possible discovering Milan.

Start your sightseeing in the city with a visit to the fantastic Piazza Gae Aulenti. This square is a popular stop on travelers’ itineraries in Milan, with an average rating of 4.6 out of 5 stars by 30,398 visitors.

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

Exploring new places can make you hungry. When you’re ready for dinner, we recommend trying one of the finest restaurants in Milan.

For a culinary experience you will remember, have a look at the menu at Galleria Restaurant. With an average rating of 4.4 out of 5 stars by 2,024 customers, it’s truly one of the best restaurants in the whole of Milan.

If you feel like having something slightly different, check out Vento di Sardegna. This is one of the most recommended restaurants in the city. Considering its average rating of 4.5 out of 5 stars by 1,063 customers, it’s one that most guests enjoy.

Nero 9 is another restaurant you could book a table at tonight. This fantastic restaurant is often recommended by both travelers and locals in Milan, and has an impressive average rating of 4.5 out of 5 stars by 573 customers.

As your day in Milan is coming to an end retreat to a bar where you can celebrate the start of your exciting luxury holiday in Italy.

Make your way to The Friends Pub Milano. This bar promises a great atmosphere for your celebrations and has an average rating of 4.3 out of 5 stars by 1,689 customers.

Or, why not continue your evening at Camparino in Galleria, rated an average of 4.4 out of 5 stars among 1,473 guests.

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

On day 2 of your exciting luxury holiday across Italy you will continue exploring the city of Milan. You still have 2 nights left in the city. Enjoy your break from the road and spend this day sightseeing and eating at some of the best restaurants in Milan. Your accommodation will be conveniently located close to several of the best attractions in the city.

Start your sightseeing of the day with a visit to the fantastic Duomo di Milano Museum. This attraction is an art museum and has an average rating of 4.8 out of 5 stars by 138,554 visitors. Duomo di Milano Museum attracts around 341,609 visitors every year.

Next up on your agenda, you’ll find the extraordinary Galleria Vittorio Emanuele II. This attraction is rated an average of 4.7 out of 5 stars by 91,394 visitors.

If you, like many others, have been feeling curious about the spectacular Sforzesco Castle Art Library library, then you should definitely take the opportunity to visit this attraction today.

The outstanding Parco Sempione is another stop you can visit today in Milan. This park is a highly recommended attraction in the city. Rated at an average of 4.6 out of 5 stars by 72,914 visitors, it’s one many travelers find worthy of a visit.

Exploring new places makes you hungry. Luckily Milan has multiple restaurants that offer fantastic dining experiences you’ll appreciate after a long day of sightseeing.

If you’re curious about the best restaurant in Milan, make sure to check out Bice Restaurant. This restaurant is a local favorite and has an average rating of 4.3 out of 5 stars by 579 customers.

Alternatively, another top-rated restaurant in the city is Camparino in Galleria. This one-of-a-kind restaurant is rated an average of 4.4 out of 5 stars by 1,473 customers.

A common recommendation among luxury travelers who have vacationed Milan before is G. B. Bar. This restaurant has a popular menu, deserving of an average rating of 4.6 out of 5 stars by 820 customers.

If you’re not yet ready to head back to your hotel, check out some of the bars in the area and experience the local nightlife.

Armani/Bamboo Bar is one of the best bars in Milan and the perfect place for an after-dinner drink. This bar has an average rating of 4.3 out of 5 stars by 272 customers.

Equally popular, this bar offers a great drink list and a nice atmosphere for your celebrations.

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

On day 3 of your luxury road trip holiday in Italy you will have the opportunity to experience two destinations in one day, the city of Milan and the city of Florence. You’ll stay in Florence for 2 nights.

Your day starts in Milan. Give yourself time to see some of the city’s very best attractions before it's time to hit the road.

Make the amazing Pisa Cathedral your first stop of the day. The average rating of 4.8 out of 5 stars by 8,361 visitors gives you an idea of what to expect from this cathedral and attraction before you head there.

Next up, make a stop at the incredible Piazza del Duomo, Pisa. With an average rating of 4.7 out of 5 stars by 104,550 visitors, it's easy to understand why so many people visit this square and attraction.

Another unforgettable travel destination you can visit on this day of your luxury holiday is the outstanding Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars by 116,882 visitors. Up to 3,200,000 travelers come to Milan every year to see the stunning Leaning Tower of Pisa with their own eyes.

Make the most of your day in Milan by joining exclusive tours and activities that take your luxury holiday in Italy to the next level. This is only one of many experiences you can include in your luxury travel package in Italy. So make sure to check out the other options too, to find the best way to spend your time in Milan today.

By the end of the day, you will drive to the city of Florence, where you will choose among some of the best luxury hotels.

After a long day of driving and exploring, we recommend you try Ristorante Paoli, one of the best restaurants in Florence. This restaurant has an average rating of 4.9 out of 5 stars by 6,031 customers.

If you feel like having something else, locals also recommend Ristorante Oliviero 1962 as one of their top choices in the city. Ristorante Oliviero 1962 is rated an average of 4.7 out of 5 stars by 1,046 customers.

Another restaurant you could try in Florence is Il Vezzo. This lovely restaurant has a fantastic menu and has been rated an average of 4.8 out of 5 stars by 862 customers.

If you’re not yet ready to head back to your hotel, we recommend you check out the nightlife of the city.

Manifattura is one of the best bars you can visit in Florence tonight. This bar is rated an average of 4.7 out of 5 stars by 509 customers.

You can also enjoy a glass or two at a popular place like Ditta Artigianale. This bar has an average rating of 4.3 out of 5 stars from 1,877 customers.

Alternatively, try Archea Brewery. Archea Brewery is the perfect place to get to know some locals in the city. This top-recommended bar is rated an average of 4.7 out of 5 stars by 723 customers.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s adventures.

On day 4 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.

Today you will have the opportunity to visit multiple popular travel destinations in Milan. Begin your sightseeing with a visit to the outstanding Central Market. This attraction has an average rating of 4.4 out of 5 stars by 43,100 visitors.

When you’re finished at Central Market, make a stop at the wonderful Cathedral of Santa Maria del Fiore. This incredible attraction is a church, rated an average of 4.8 out of 5 stars by 76,359 visitors.

Next up, make your way to one of the best places to see according to travelers in Milan, the extraordinary Galleria dell'Accademia. This national museum gets around 1,719,645 visits annually and is rated an average of 4.6 out of 5 stars by 34,429 visitors.

As the day moves along, another attraction you will probably want to visit is the incredible David. Up to 10,476 visitors have rated this statue an average of 4.8 out of 5 stars.

If you’re up for one last attraction today, check out the popular piazzale Michelangelo.

Tonight you will stay at one of the best luxury hotels in Milan. We have selected the perfect options for you to have the loveliest experience in Milan.

Treat yourself to an overnight stay at the wonderful B&B Hotel Firenze Novoli, a highly recommended 3-star hotel in the city. This hotel has an average rating of 4 out of 5 stars by 1,147 guests and guarantees you a pleasant break from your self-drive luxury vacation.

Another excellent luxury accommodation alternative in Milan is the fantastic Select Executive. This 4-star apartment is the ultimate place to lay back and treat yourself to some well-deserved downtime after a busy day exploring.

Alternatively, check in at the outstanding Ville sull'Arno. This 5-star hotel is warmly recommended by previous guest and has an average rating of 4.5 out of 5 stars from 1,245 reviews to prove it. Get cozy and rest before it’s yet again time to hit the roads.

Our flexible booking system will automatically provide you with the best luxury hotel alternatives if these are not available.

After a long day of exploring, it’s time for indulging in some food. Make a reservation at one of the best restaurants in Milan.

We recommend you eat at a restaurant that locals enjoy, like the fantastic Ristorante Le Volte Firenze. This excellent restaurant has an average rating of 4.7 out of 5 stars by 536 customers.

Alternatively, check out the menu at Le Cappelle Medicee. Considered one of the best restaurants in Milan, it has an average rating of 4.6 out of 5 stars by 1,574 customers.

If you’re curious about more of the best restaurants in Milan, Ditta Artigianale is one to check out. Ditta Artigianale is rated an average of 4.3 out of 5 stars by 1,877 customers.

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 Milan.

Many locals go to Locale Firenze to have a good time. This bar is rated an average of 4.6 out of 5 stars by 771 customers.

If you feel like going somewhere else, another popular option in the city is Djària - American Bar. This bar has an average rating of 4.8 out of 5 stars by 182 customers.

Caffe San Firenze is another great option in Milan. This bar is rated an average of 4.3 out of 5 stars by 1,268 customers.

Enjoy an amazing evening in Milan, and get ready for more fantastic days to come of your luxury vacation in Italy!

On day 5 of your luxury road trip holiday in Italy you will have the opportunity to experience two destinations in one day, the city of Milan and the city of Rome. You’ll stay in Rome for 3 nights.

Your day starts in Milan. Give yourself time to see some of the city’s very best attractions before it's time to hit the road.

Make the amazing piazza della Signoria your first stop of the day. The average rating of 4.8 out of 5 stars by 66,956 visitors gives you an idea of what to expect from this square and attraction before you head there.

Next up, make a stop at the incredible Ponte Vecchio. With an average rating of 4.7 out of 5 stars by 118,099 visitors, it's easy to understand why so many people visit this deck arch bridge and attraction.

Another unforgettable travel destination you can visit on this day of your luxury holiday is the outstanding Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars by 61,794 visitors. Up to 2,011,219 travelers come to Milan every year to see the stunning Uffizi Gallery with their own eyes.

When you’re finished at the church, the perfect next stop is the popular Basilica of Santa Croce in Florence. This spectacular church and attraction is rated an average of 4.7 out of 5 stars in 28,544 reviews.

Make the most of your day in Milan by joining exclusive tours and activities that take your luxury holiday in Italy to the next level. This is only one of many experiences you can include in your luxury travel package in Italy. So make sure to check out the other options too, to find the best way to spend your time in Milan today.

By the end of the day, you will drive to the city of Rome, where you will choose among some of the best luxury hotels.

After a long day of driving and exploring, we recommend you try Cantina e Cucina, one of the best restaurants in Rome. This restaurant has an average rating of 4.6 out of 5 stars by 7,907 customers.

If you feel like having something else, locals also recommend Ai Tre Scalini as one of their top choices in the city. Ai Tre Scalini is rated an average of 4.4 out of 5 stars by 2,950 customers.

Another restaurant you could try in Rome is 433. This lovely restaurant has a fantastic menu and has been rated an average of 4.4 out of 5 stars by 2,341 customers.

If you’re not yet ready to head back to your hotel, we recommend you check out the nightlife of the city.

D’Angelo Caffè & Gastronomia - Bar Bistro Caffetteria Napoletana a Roma is one of the best bars you can visit in Rome tonight. This bar is rated an average of 4.7 out of 5 stars by 1,054 customers.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s adventures.

On day 6 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Milan. You’ll stay in Milan 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 Milan to the fullest.

Today you will have the opportunity to visit multiple popular travel destinations in Milan. Begin your sightseeing with a visit to the outstanding Colosseum. This attraction has an average rating of 4.7 out of 5 stars by 328,821 visitors and attracts around 7,400,000 curious travelers every year.

When you’re finished at Colosseum, make a stop at the wonderful Roman Forum. This incredible attraction is a square, rated an average of 4.7 out of 5 stars by 114,450 visitors.

Next up, make your way to one of the best places to see according to travelers in Milan, the extraordinary Pantheon. This roman temple gets around 30,000,000 visits annually and is rated an average of 4.8 out of 5 stars by 189,682 visitors.

As the day moves along, another attraction you will probably want to visit is the incredible Piazza Navona. Up to 158,771 visitors have rated this square an average of 4.7 out of 5 stars.

If you’re up for one last attraction today, check out the popular Castel Sant'Angelo. This attraction is a museum, rated an average 4.7 out of 5 stars among 72,431 visitors and attracts around 918,591 visits each year.

Tonight you will stay at one of the best luxury hotels in Milan. We have selected the perfect options for you to have the loveliest experience in Milan.

Treat yourself to an overnight stay at the wonderful Hotel Sirenetta, a highly recommended 3-star hotel in the city. This hotel has an average rating of 4.1 out of 5 stars by 4,089 guests and guarantees you a pleasant break from your self-drive luxury vacation.

Another excellent luxury accommodation alternative in Milan is the fantastic Relais Castrum Boccea. This 4-star hotel is the ultimate place to lay back and treat yourself to some well-deserved downtime after a busy day exploring. Relais Castrum Boccea is rated an average of 4 out of 5 stars by 630 guests.

Alternatively, check in at the outstanding Hotel Caravita. This 5-star hotel is warmly recommended by previous guest and has an average rating of 4.4 out of 5 stars from 262 reviews to prove it. Get cozy and rest before it’s yet again time to hit the roads.

Our flexible booking system will automatically provide you with the best luxury hotel alternatives if these are not available.

After a long day of exploring, it’s time for indulging in some food. Make a reservation at one of the best restaurants in Milan.

We recommend you eat at a restaurant that locals enjoy, like the fantastic Roma Sparita. This excellent restaurant has an average rating of 4.4 out of 5 stars by 2,073 customers.

Alternatively, check out the menu at Ristorante Amedeo. Considered one of the best restaurants in Milan, it has an average rating of 4.3 out of 5 stars by 1,798 customers.

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 Milan.

Many locals go to VinAllegro to have a good time. This bar is rated an average of 4.3 out of 5 stars by 1,167 customers.

If you feel like going somewhere else, another popular option in the city is Ristorante Tema. This bar has an average rating of 4.4 out of 5 stars by 939 customers.

Bar Tornatora Rome is another great option in Milan. This bar is rated an average of 4.3 out of 5 stars by 952 customers.

Enjoy an amazing evening in Milan, and get ready for more fantastic days to come of your luxury vacation in Italy!

On day 7 of your exciting luxury holiday across Italy you will continue exploring the city of Milan. 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 Milan. Your accommodation will be conveniently located close to several of the best attractions in the city.

Start your sightseeing of the day with a visit to the fantastic Altare della Patria. This attraction is an architectural structure and has an average rating of 4.8 out of 5 stars by 49,843 visitors. Altare della Patria attracts around 1,683,070 visitors every year.

Next up on your agenda, you’ll find the extraordinary Trevi Fountain. This attraction is rated an average of 4.8 out of 5 stars by 343,494 visitors.

If you, like many others, have been feeling curious about the spectacular Piazza di Spagna square, then you should definitely take the opportunity to visit this attraction today.

The outstanding piazza del Popolo is another stop you can visit today in Milan. This square is a highly recommended attraction in the city. Rated at an average of 4.6 out of 5 stars by 89,807 visitors, it’s one many travelers find worthy of a visit.

If you want to experience even more of Milan, then consider a visit to the incredible Villa Borghese. Villa Borghese is an urban zone of rome and popular attraction most travelers enjoy. More than 69,749 people have rated this attraction an average of 4.6 out of 5 stars.

Exploring new places makes you hungry. Luckily Milan has multiple restaurants that offer fantastic dining experiences you’ll appreciate after a long day of sightseeing.

If you’re curious about the best restaurant in Milan, make sure to check out La Taverna dei Fori Imperiali. This restaurant is a local favorite and has an average rating of 4.4 out of 5 stars by 1,637 customers.

Alternatively, another top-rated restaurant in the city is Maccheroni. This one-of-a-kind restaurant is rated an average of 4.3 out of 5 stars by 1,633 customers.

A common recommendation among luxury travelers who have vacationed Milan before is Coso Ristorante. This restaurant has a popular menu, deserving of an average rating of 4.3 out of 5 stars by 1,275 customers.

If you’re not yet ready to head back to your hotel, check out some of the bars in the area and experience the local nightlife.

La Botticella of Poggi Giovanni is one of the best bars in Milan and the perfect place for an after-dinner drink. This bar has an average rating of 4.7 out of 5 stars by 655 customers.

You may also want to check out Tigelleria Romana - Bistrot & Cafè. Equally popular, this bar offers a great drink list and a nice atmosphere for your celebrations. Tigelleria Romana - Bistrot & Cafè is rated an average of 4.3 out of 5 stars by 792 customers.

Alternatively, head out to La Licata. La Licata has an average rating of 4.5 out of 5 stars by 2,067 customers and is a top choice among travelers as well as locals.

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

On day 8 of your luxury road trip holiday in Italy you will have the opportunity to experience two destinations in one day, Milan and the city of Arezzo. You’ll stay in Arezzo for 1 night.

Your day starts in Milan.

Make the amazing St. Peter's Basilica your first stop of the day. The average rating of 4.8 out of 5 stars by 131,043 visitors gives you an idea of what to expect from this major basilica and attraction before you head there. More than 11,000,000 people visit this attraction every year.

Next up, make a stop at the incredible Sistine Chapel. With an average rating of 4.7 out of 5 stars by 52,083 visitors, it's easy to understand why so many people visit this chapel and attraction.

Another unforgettable travel destination you can visit on this day of your luxury holiday is the outstanding Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars by 38,954 visitors.

When you’re finished at the art museum, the perfect next stop is the popular Vatican Museums. This spectacular art museum and attraction is rated an average of 4.6 out of 5 stars in 133,310 reviews. Vatican Museums attracts about 1,612,530 visitors annually.

Make the most of your day in Milan by joining exclusive tours and activities that take your luxury holiday in Italy to the next level. This is only one of many experiences you can include in your luxury travel package in Italy. So make sure to check out the other options too, to find the best way to spend your time in Milan today.

By the end of the day, you will drive to the city of Arezzo, where you will choose among some of the best luxury hotels.

After a long day of driving and exploring, we recommend you try Il Covo dei Briganti, one of the best restaurants in Arezzo. This restaurant has an average rating of 4.7 out of 5 stars by 509 customers.

If you feel like having something else, locals also recommend Trattoria Il Saraceno as one of their top choices in the city. Trattoria Il Saraceno is rated an average of 4.3 out of 5 stars by 1,759 customers.

Another restaurant you could try in Arezzo is Antica Fonte. This lovely restaurant has a fantastic menu and has been rated an average of 4.6 out of 5 stars by 1,306 customers.

If you’re not yet ready to head back to your hotel, we recommend you check out the nightlife of the city.

La Clandestina is one of the best bars you can visit in Arezzo tonight. This bar is rated an average of 4.6 out of 5 stars by 277 customers.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s adventures.

On day 9 of your luxury road trip holiday in Italy you will have the opportunity to experience two destinations in one day, the city of Milan and the city of Milan. You’ll stay in Milan for 1 night.

Your day starts in Milan. Give yourself time to see some of the city’s very best attractions before it's time to hit the road.

Make the amazing piazza Grande your first stop of the day. The average rating of 4.6 out of 5 stars by 14,465 visitors gives you an idea of what to expect from this square and attraction before you head there.

Next up, make a stop at the incredible Arezzo Cathedral. With an average rating of 4.6 out of 5 stars by 2,450 visitors, it's easy to understand why so many people visit this cathedral and attraction.

Another unforgettable travel destination you can visit on this day of your luxury holiday is the outstanding San Francesco, Arezzo. This minor basilica has an average rating of 4.6 out of 5 stars by 2,377 visitors. Up to 20,939 travelers come to Milan every year to see the stunning San Francesco, Arezzo with their own eyes.

Make the most of your day in Milan by joining exclusive tours and activities that take your luxury holiday in Italy to the next level. This is only one of many experiences you can include in your luxury travel package in Italy. So make sure to check out the other options too, to find the best way to spend your time in Milan today.

By the end of the day, you will drive to the city of Milan, where you will choose among some of the best luxury hotels.

After a long day of driving and exploring, we recommend you try DeRos Restaurant, one of the best restaurants in Milan. This restaurant has an average rating of 4.7 out of 5 stars by 285 customers.

If you feel like having something else, locals also recommend Dessert Bar Milano as one of their top choices in the city. Dessert Bar Milano is rated an average of 5 out of 5 stars by 144 customers.

Another restaurant you could try in Milan is Alto Ristorante. This lovely restaurant has a fantastic menu and has been rated an average of 4.8 out of 5 stars by 137 customers.

If you’re not yet ready to head back to your hotel, we recommend you check out the nightlife of the city.

Carico is one of the best bars you can visit in Milan tonight. This bar is rated an average of 4.4 out of 5 stars by 125 customers.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s adventures.

Today is the last day of your 10-day luxury holiday in Italy and it’s soon time to start your journey home. This is your chance to get one last glimpse of Milan before saying goodbye.

Catch a later flight to enjoy some extra time for exploring. If you have a late departure, we recommend doing some last-minute shopping or sightseeing.

Make the most of what’s left of your luxury vacation in Italy by heading out to the stunning Arch of Peace. This extraordinary monument and attraction is rated an average of 4.6 out of 5 stars in 27,502 reviews, and is an excellent choice for your last sightseeing in Milan.

Don’t end your vacation hungry. For one last meal in the city of Milan, check out the menu at Carico. This popular restaurant is rated an average of 4.4 out of 5 stars by 125 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!