Luxury 9-Day Italy Road Trip from Rome traveling north to Arezzo, Florence, and Siena

Your luxury holiday in Italy begins as soon as you reach the city of Rome. 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 Rome - a city with many fantastic attractions to explore. Catch an early flight to enjoy as much time as possible discovering Rome.

Start your sightseeing in the city with a visit to the fantastic Altare della Patria. This architectural structure is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.8 out of 5 stars by 49,843 visitors. Around 1,683,070 people visit this attraction every year.

Tonight you will be treated to a stay at one of best luxury hotels in Rome. 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 Rome.

For a culinary experience you will remember, have a look at the menu at 433. With an average rating of 4.4 out of 5 stars by 2,341 customers, it’s truly one of the best restaurants in the whole of Rome.

If you feel like having something slightly different, check out Roma Sparita. This is one of the most recommended restaurants in the city. Considering its average rating of 4.4 out of 5 stars by 2,073 customers, it’s one that most guests enjoy.

As your day in Rome 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 D’Angelo Caffè & Gastronomia - Bar Bistro Caffetteria Napoletana a Roma. This bar promises a great atmosphere for your celebrations and has an average rating of 4.7 out of 5 stars by 1,054 customers.

Or, why not continue your evening at Cantina e Cucina, rated an average of 4.6 out of 5 stars among 7,907 guests.

Another bar where you can have a great time tonight is Ai Tre Scalini. This bar has an average rating of 4.4 out of 5 stars by 2,950 customers.

Raise a toast to the start of your 9-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 Rome. You still have 3 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 Rome. 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 Colosseum. This attraction is a roman amphitheatre and has an average rating of 4.7 out of 5 stars by 328,821 visitors. Colosseum attracts around 7,400,000 visitors every year.

Next up on your agenda, you’ll find the extraordinary Roman Forum. This attraction is rated an average of 4.7 out of 5 stars by 114,450 visitors.

If you, like many others, have been feeling curious about the spectacular Pantheon roman temple, then you should definitely take the opportunity to visit this attraction today. Pantheon has an average rating of 4.8 out of 5 stars by 189,682 visitors and is visited by up to 30,000,000 people every year.

The outstanding Piazza Navona is another stop you can visit today in Rome. This square is a highly recommended attraction in the city. Rated at an average of 4.7 out of 5 stars by 158,771 visitors, it’s one many travelers find worthy of a visit.

If you want to experience even more of Rome, then consider a visit to the incredible Castel Sant'Angelo. Castel Sant'Angelo is a museum and popular attraction most travelers enjoy. More than 72,431 people have rated this attraction an average of 4.7 out of 5 stars. If you decide to visit this museum, you’ll be one of 918,591 people who do so every year.

Exploring new places makes you hungry. Luckily Rome 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 Rome, make sure to check out Ristorante Amedeo. This restaurant is a local favorite and has an average rating of 4.3 out of 5 stars by 1,798 customers.

Alternatively, another top-rated restaurant in the city is La Taverna dei Fori Imperiali. This one-of-a-kind restaurant is rated an average of 4.4 out of 5 stars by 1,637 customers.

A common recommendation among luxury travelers who have vacationed Rome before is Maccheroni. This restaurant has a popular menu, deserving of an average rating of 4.3 out of 5 stars by 1,633 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.

VinAllegro is one of the best bars in Rome and the perfect place for an after-dinner drink. This bar has an average rating of 4.3 out of 5 stars by 1,167 customers.

You may also want to check out Ristorante Tema. Equally popular, this bar offers a great drink list and a nice atmosphere for your celebrations. Ristorante Tema is rated an average of 4.4 out of 5 stars by 939 customers.

Alternatively, head out to Bar Tornatora Rome. Bar Tornatora Rome has an average rating of 4.3 out of 5 stars by 952 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.

Day 3 of your luxury road trip Italy offers you another day to explore the magnificent city of Rome. Today you will continue your luxury holiday in the best possible way - by discovering the best sights, most exciting activities, and finest restaurants in the city.

One of the best travel destinations you can visit in Rome today is the stunning Trevi Fountain. This sculpture has an average rating of 4.8 out of 5 stars in 343,494 reviews.

Next up, make your way to the spectacular Piazza di Spagna. This attraction is a square and has an average rating of 4.7 out of 5 stars by 113,658 visitors.

When you’re ready for your next sight of the day, continue to the incredible Spanish Steps. This attraction is a monumental staircase and has an average rating of 4.5 out of 5 stars by 57,211 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit the fantastic piazza del Popolo. This square and travel destination is rated an average of 4.6 out of 5 stars by 89,807 visitors.

If you’re keen to explore even more, then consider a visit to the outstanding Villa Borghese. This urban zone of rome is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 69,749 visitors.

You will be excited to learn that there are plenty of options for luxury tours and bespoke activities in Rome. Add the best tours to your luxury vacation package before or after booking.

After a long day of discovering the unique quirks of Rome, it’s an excellent idea to sit down for a lovely meal. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

According to reviews, Coso Ristorante is one of the absolute best places to eat in Rome. At this restaurant, you’ll enjoy a great atmosphere and a fantastic food and drinks menu. Coso Ristorante is rated an average of 4.3 out of 5 stars by 1,275 customers.

Alternatively, if you’re curious to try a local favorite, check out Pierluigi. This restaurant is rated an average of 4.3 out of 5 stars by 1,123 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 Ad Hoc a visit instead. This restaurant is a top recommendation often mentioned by both travelers and locals. Ristorante Ad Hoc has an average rating of 4.6 out of 5 stars by 752 customers.

If you feel like it, head out to a bar to celebrate another fantastic day in Rome and take the pulse of the city’s nightlife.

To get a drink at one of the best bars in the city, go to La Botticella of Poggi Giovanni. This bar has an average rating of 4.7 out of 5 stars by 655 customers.

If you’d like to continue your evening somewhere else, we recommend heading to Tigelleria Romana - Bistrot & Cafè. This bar is rated an average of 4.3 out of 5 stars by 792 customers.

A third bar where you could have a great time tonight is La Licata. This bar has an average rating of 4.5 out of 5 stars by 2,067 customers.

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

On day 4 of your luxury road trip holiday in Italy you will have the opportunity to experience two destinations in one day, Vatican City and the city of Arezzo. You’ll stay in Arezzo for 1 night.

Your day starts in Vatican City.

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 Vatican City 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 Vatican City 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 Antica Fonte, one of the best restaurants in Arezzo. This restaurant has an average rating of 4.6 out of 5 stars by 1,306 customers.

If you feel like having something else, locals also recommend Trattoria Cavour 42 as one of their top choices in the city. Trattoria Cavour 42 is rated an average of 4.6 out of 5 stars by 909 customers.

Another restaurant you could try in Arezzo is Il Cantuccio. This lovely restaurant has a fantastic menu and has been rated an average of 4.3 out of 5 stars by 1,027 customers.

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

Il Covo dei Briganti is one of the best bars you can visit in Arezzo 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 Trattoria Il Saraceno. This bar has an average rating of 4.3 out of 5 stars from 1,759 customers.

Alternatively, try La Clandestina. La Clandestina is the perfect place to get to know some locals in the city. This top-recommended 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 5 of your luxury road trip holiday in Italy you will have the opportunity to experience two destinations in one day, the city of Bologna and the city of Florence. You’ll stay in Florence for 2 nights.

Your day starts in Bologna. 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 Bologna every year to see the stunning San Francesco, Arezzo with their own eyes.

Make the most of your day in Bologna 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 Bologna 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 6 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Florence. You’ll stay in Florence 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 Florence to the fullest.

Today you will have the opportunity to visit multiple popular travel destinations in Florence. Begin your sightseeing with a visit to the outstanding Ponte Vecchio. This attraction has an average rating of 4.7 out of 5 stars by 118,099 visitors.

When you’re finished at Ponte Vecchio, make a stop at the wonderful Uffizi Gallery. This incredible attraction is a national museum, rated an average of 4.7 out of 5 stars by 61,794 visitors. Up to 2,011,219 people visit this fantastic attraction every year.

Next up, make your way to one of the best places to see according to travelers in Florence, the extraordinary piazza della Signoria. This square is rated an average of 4.8 out of 5 stars by 66,956 visitors.

As the day moves along, another attraction you will probably want to visit is the incredible Basilica of Santa Croce in Florence. Up to 28,544 visitors have rated this church an average of 4.7 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 Florence. We have selected the perfect options for you to have the loveliest experience in Florence.

Treat yourself to an overnight stay at the wonderful Argentina , a highly recommended 3-star hotel in the city. This hotel has an average rating of 4.1 out of 5 stars by 2,994 guests and guarantees you a pleasant break from your self-drive luxury vacation.

Another excellent luxury accommodation alternative in Florence is the fantastic Nil Hotel. This 4-star hotel is the ultimate place to lay back and treat yourself to some well-deserved downtime after a busy day exploring. Nil Hotel is rated an average of 4.1 out of 5 stars by 3,288 guests.

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 1,297 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 Florence.

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 Florence, 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 Florence, La Giostra is one to check out. La Giostra is rated an average of 4.4 out of 5 stars by 1,432 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 Florence.

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 Florence. This bar is rated an average of 4.3 out of 5 stars by 1,268 customers.

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

Get ready for day 7 of your luxury vacation in Italy. On this day of your exciting road trip holiday, you will have the most wonderful time discovering Florence and Pisa. You’ll stay in Siena for 1 night. Enjoy a flexible travel itinerary and choose how much time you want to spend at each destination.

Start your day with one of travelers’ favorite attractions in Florence, the incredible Cathedral of Santa Maria del Fiore. This popular attraction is a church that has been rated an average of 4.8 out of 5 stars by 76,359 visitors.

Today we also recommend you visit the amazing Brunelleschi's dome, an outstanding dome in Florence. Around 6,199 travelers have rated this attraction an average of 4.8 out of 5 stars.

Another of the best travel destinations you can visit in Florence is the astonishing Central Market. This attraction is a must-see tourist destination and has been rated an average of 4.4 out of 5 stars in 43,100 reviews.

To experience the local culture, see the best attractions, and meet new people at the same time, add a tour or activity to your luxury holiday package in Italy. As a luxury traveler, you will choose among only the best experiences available to you on this day of your exclusive road trip vacation in Florence.

It’s now time to get back on the road and continue to the next destination of your day, the city of Pisa.

Make your way to the incredible Leaning Tower of Pisa for some unforgettable sightseeing in Pisa. This popular attraction is a bell tower and has an average rating of 4.7 out of 5 stars by 116,882 visitors. Approximately 3,200,000 people visit Pisa every year to see the fantastic Leaning Tower of Pisa.

Next up, steer your step in the direction of Piazza del Duomo, Pisa. This outstanding attraction has an average rating of 4.7 out of 5 stars by 104,550 travelers and is one of the most fantastic places to visit in Pisa.

Today you’ll check in at one of the most exclusive hotels in the city of Siena. Luxury hotels in Siena offer fantastic facilities and wonderful rooms. In combination with staff that is generous with both their time and recommendations, you’re guaranteed a pleasant

Stay in Siena.

After a long day of traveling and sightseeing, we recommend you try one of the best restaurants in Siena, Osteria degli Svitati. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.7 out of 5 stars from 911 reviews.

Locals also recommend Osteria Il Carroccio as one of the best restaurants to have dinner at in Siena. The Osteria Il Carroccio is rated an average of 4.7 out of 5 stars by 895 customers, including locals as well as travelers.

For a slightly different culinary experience, book a table at Antica Trattoria Papei. This popular restaurant has an average rating of 4.3 out of 5 stars by 3,761 customers.

Depending on your plans for tomorrow, you might want to head back to your hotel for some relaxation. If not, this is your chance to take the temperature of Siena's nightlife.

If you’re not quite ready for bed yet, head off to a popular bar like La Taverna di San Giuseppe. This bar is rated an average of 4.7 out of 5 stars from 1,767 customers.

Another place you could go for some drinks is the top-rated Ristorante Gallo Nero. Often recommended by locals, this bar is an excellent place to check out tonight. Ristorante Gallo Nero has an average rating of 4.4 out of 5 stars by 829 customers.

Alternatively, go to San Paolo Pub. Rated an average of 4.3 out of 5 stars in 704 reviews, it’s one worth checking out if you’re in the party mood.

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

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

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

Make the amazing Tower of Mangia your first stop of the day. The average rating of 4.6 out of 5 stars by 673 visitors gives you an idea of what to expect from this top-tier point of interest and attraction before you head there.

Next up, make a stop at the incredible piazza del Campo. With an average rating of 4.8 out of 5 stars by 64,175 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 Siena Cathedral. This domus has an average rating of 4.8 out of 5 stars by 21,656 visitors.

When you’re finished at the fortress, the perfect next stop is the popular Fortezza Medicea (Siena). This spectacular fortress and attraction is rated an average of 4.5 out of 5 stars in 9,835 reviews.

Make the most of your day in Siena 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 Siena 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 Antica Pesa, one of the best restaurants in Rome. This restaurant has an average rating of 4.4 out of 5 stars by 858 customers.

If you feel like having something else, locals also recommend Hostaria Isidoro as one of their top choices in the city. Hostaria Isidoro is rated an average of 4.3 out of 5 stars by 909 customers.

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

Cappuccino Bar 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 272 customers.

You can also enjoy a glass or two at a popular place like Wine Bar All Brothers. This bar has an average rating of 4.4 out of 5 stars from 308 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 9-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 Rome 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 Campo de' Fiori. This extraordinary square and attraction is rated an average of 4.4 out of 5 stars in 51,133 reviews, and is an excellent choice for your last sightseeing in Rome.

Don’t end your vacation hungry.

You will then say farewell to Rome 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!