Luxury 5-Day Italy Road Trip from Florence traveling east to Arezzo and Rome

Your luxury holiday in Italy begins as soon as you reach the city of Florence, where you'll be staying for 1 night. 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 Florence. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

When you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

Enoteca Pinchiorri is the Bib Gourmand restaurant to visit if you’re craving culinary excellence. This 3-star Michelin restaurant has a diverse and enticing menu selection, which includes its delicious and signature italian contemporary meals.

Elevate your dining experience at a 2-star Michelin restaurant in Florence, Santa Elisabetta. At this Bib Gourmand awardee, savor a combination of exceptional flavors with a memorable dining experience. This renowned restaurant’s meal selection includes its signature creative and mediterranean dishes, which are sure to tickle your taste buds.

Another culinary gem in Florence you shouldn’t miss is Il Palagio. Enjoy a menu that has earned it a prestigious 1-star Michelin rating. Delivering a food experience like no other, this Bib Gourmand restaurant’s italian contemporary menu and exceptional service make it a must-visit destination for those seeking exceptional dining in the area.

As your first day in Florence 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.

Whether you prefer your drink shaken or stirred, Manifattura is a great place to enjoy a well-deserved celebratory drink. This bar is rated an average of 4.7 out of 5 stars from 509 customers.

Alternatively, check out Caffe Concerto Paszkowski, a place many travelers consider their favorite in Florence. Caffe Concerto Paszkowski offers drinks for every taste and is rated an average of 4.7 out of 5 stars by 509 guests.

If you want to continue your night at another bar, try Ristorante Buca Mario and soak in its inviting ambiance. This bar is one of the best drinking spots in Florence and is rated an average of 4.4 out of 5 stars in 1,879 reviews.

Raise a toast to the start of your 5-day luxury vacation in Italy and look forward to more fantastic days to come!

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence 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.

Your sightseeing of the day begins at piazza della Signoria, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Next, satisfy your wanderlust at Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars from 61,794 travelers. Given the site's popularity, it’s easy to understand why more than 2,011,219 people visit it every year.

Ponte Vecchio is another must-visit attraction. This renowned deck arch bridge offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 118,099 travelers, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Piazza della Repubblica. This well-loved square boasts a 4.6 out of 5-star rating from 22,356 reviews.

When there’s still energy left for exploring, Cathedral of Santa Maria del Fiore awaits. If you’ve been interested in experiencing a church, this is a top pick rated 4.8 out of 5 stars by 76,359 previous visitors.

Set your GPS to Arezzo and hit the road. Expect a journey of approximately 1 hour 4 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Arezzo beckons with new experiences!

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 Arezzo.

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

According to reviews, Il Covo dei Briganti is one of the absolute best places to eat in Arezzo. At this restaurant, you’ll enjoy a great atmosphere and a fantastic food and drinks menu. Il Covo dei Briganti is rated an average of 4.7 out of 5 stars by 509 customers.

Alternatively, if you’re curious to try a local favorite, check out Trattoria Il Saraceno. This restaurant is rated an average of 4.3 out of 5 stars by 1,759 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 Antica Fonte a visit instead. This restaurant is a top recommendation often mentioned by both travelers and locals. Antica Fonte has an average rating of 4.6 out of 5 stars by 1,306 customers.

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

If you’re up for classic drinks with a modern flair, consider going to La Clandestina. Around 277 customers have given this incredible bar an average rating of 4.6 out of 5 stars.

Locals of Arezzo also enjoy the cocktails at Emilio. This place is rated an average of 4.6 out of 5 stars by 263 customers and is one of the best you can experience in the city.

Another top-rated alternative for an expertly crafted celebratory drink is La Nuova Tagliatella. This bar has an average rating of 4.4 out of 5 stars by 275 customers.

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

Wake up to day 3 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Arezzo, Cortona, and Rome. 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 Rome adds a touch of comfort to your journey.

When you’re ready for some sightseeing, make your way to San Francesco, Arezzo. This much-appreciated minor basilica is rated 4.6 out of 5 stars in 2,377 reviews. Each year, 20,939 people visit this site to admire its unique features.

Next up is piazza Grande. This square has an average rating of 4.6 out of 5 stars from 14,465 visitors.

Another top sightseeing recommendation is Arezzo Cathedral. This cathedral has been rated 4.6 out of 5 stars in 2,450 reviews.

Fasten your seatbelt and make your way to your next stop. Cortona, 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 Arezzo to Cortona may take around 46 min without traffic disruptions. Upon arrival, we highly recommend checking out some of the top attractions.

When you’re ready to jump back into the car and say goodbye to Cortona, you’ll hit the road in the direction of Rome. This drive usually takes around 2 hours 38 min. When you arrive, enjoy some sightseeing.

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 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.

One of the top restaurants in the area is Tonnarello. This amazing restaurant offers great food meticulously prepared with the freshest ingredients. Over 62,881 diners have left the restaurant with an average rating of 4.7 out of 5 stars.

Another restaurant that many travelers recommend is Ristorante Pancrazio dal 1922. Rated an average of 4.7 out of 5 stars by 2,946 customers, this restaurant is praised for its variety of dishes, warm ambiance, and amazing service.

You can also try the delicious food served at Cantina e Cucina for a unique dining experience. 7,907 tourists and locals alike have approved of this restaurant by giving it an average rating of 4.6 out of 5 stars in reviews.

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.

Many locals go to RoYaL Art Cafè Roma for an evening cocktail or glass of wine. This bar is rated an average of 4.4 out of 5 stars by 3,972 customers.

If you feel like going somewhere else, another popular option in the city is Ai Tre Scalini. This bar has an average rating of 4.4 out of 5 stars by 2,950 customers.

Centro is another great option in Rome, offering excellent drinks and a great atmosphere. This bar is rated an average of 4.4 out of 5 stars by 1,488 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.

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 1 night. The day's itinerary unfolds with a diverse array of experiences in Rome and Florence.

Be one of the day’s first visitors at Capitoline Hill. This hill is rated an average of 4.7 out of 5 stars by 19,557 visitors.

When you’re finished at Capitoline Hill, head to Roman Forum. This one-of-a-kind square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Colosseum. This roman amphitheatre is rated an average of 4.7 out of 5 stars by 328,821 visitors. Visiting Colosseum means you'll be one of 7,400,000 people who do so every year.

If you’re keen to explore more, then consider a visit to Pantheon. This roman temple is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 189,682 visitors. Around 30,000,000 travelers visit Pantheon every year.

To round off your sightseeing experience, make your way to Trevi Fountain. This famous sculpture is rated an average of 4.8 out of 5 stars by 343,494 travelers.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Florence. 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 3 hours 12 min. Upon reaching Florence, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

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 Florence.

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

At the top-rated restaurant Il Vezzo, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.8 out of 5 stars by 862 customers.

If you feel like having something else, Le Vespe Cafè is another great option. This fantastic restaurant has an average rating of 4.7 out of 5 stars by 773 customers.

A third restaurant you could check out is Ristorante Le Volte Firenze. Ristorante Le Volte Firenze offers a menu of delicious dishes that are sure to satisfy your hunger. We'll let its excellent rating of 4.7 out of 5 stars by 536 customers speak for itself.

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

When an after-dinner drink sounds enticing, visit Villa Cora, one of the best bars in the city of Florence. This bar has an average rating of 4.8 out of 5 stars from 699 customers.

Get drinks as good as this day's adventure at Osteria Tripperia Il Magazzino. Considered one of the most popular bars in the city of Florence, this bar is rated an average of 4.4 out of 5 stars by 951 customers.

Archea Brewery is also a great bar where you can have nice chats over delicious bites. Archea Brewery has an average rating of 4.7 out of 5 stars from 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.

Today is the last day of your 5-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 Florence before saying goodbye.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Florence’s celebrated shopping district. Thanks to your stay’s premier location, you can easily visit the city’s commercial hubs and wander through its diverse range of local shops without rushing.

Whether you’re on a hunt for an ideal present to give to your friends or family, or looking for a personal memento to remind you of Italy, a variety of items are waiting for you.

Don’t travel hungry. Take the opportunity to savor the local cuisine in Florence one last time before you head to the airport.

One of the top restaurants in the area is Ala Grande Caffè(caffè Rosanò). This amazing restaurant offers great food meticulously prepared with the freshest ingredients. Over 2,180 diners have left the restaurant with an average rating of 4.8 out of 5 stars.

Another restaurant that many travelers recommend is Ristorante Romantico il Paiolo. Rated an average of 4.4 out of 5 stars by 2,523 customers, this restaurant is praised for its variety of dishes, warm ambiance, and amazing service.

You can also try the delicious food served at Ristorante La Spada for a unique dining experience. 2,228 tourists and locals alike have approved of this restaurant by giving it an average rating of 4.4 out of 5 stars in reviews.

You will then say farewell to Florence 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!