Luxury 5-Day Italy Road Trip from Milan to Venice and Florence

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.

When it’s time for dinner, try one of the most popular restaurants in Milan. Make sure to reserve a table in advance, as the best restaurants fill up quickly.

Do not miss out on an incredible dining experience at Enrico Bartolini al Mudec, one of the finest Bib Gourmand restaurants in Milan, boasting 3 Michelin stars. Featuring delightful food options and creative offerings, Enrico Bartolini al Mudec has garnered acclaim from numerous satisfied diners.

For local recommendations, look no further than Seta by Antonio Guida. This food haven in Milan has been awarded 2 Michelin stars. Featuring international and contemporary cuisine, this well-loved Bib Gourmand restaurant stands out as a favorite among local and international customers.

In the mood for something different? Consider reserving a table at Il Luogo Aimo e Nadia. This celebrated dining spot in Milan is renowned for its sumptuous meals and italian contemporary and modern menu. Countless patrons sing this Bib Gourmand restaurant's praises, adding to its 1 Michelin-star prestige.

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 Milan.

When an after-dinner drink sounds enticing, visit Mag Cafe, one of the best bars in the city of Milan. This bar has an average rating of 4.4 out of 5 stars from 3,270 customers.

Get drinks as good as this day's adventure at Nottingham Forest. Considered one of the most popular bars in the city of Milan, this bar is rated an average of 4.4 out of 5 stars by 2,686 customers.

The Friends Pub Milano is also a great bar where you can have nice chats over delicious bites. 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 5-day luxury vacation in Italy and look forward to more fantastic days to come!

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Milan and Venice. 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 Venice adds a touch of comfort to your journey.

Start your day with a visit to Duomo di Milano Museum. This extraordinary art museum is rated an average of 4.8 out of 5 stars by 138,554 visitors. Each year, around 341,609 people visit this site to learn more about it.

Next, make your way to Galleria Vittorio Emanuele II. This top attraction is a commercial gallery with an average rating of 4.7 out of 5 stars by 91,394 visitors.

We also recommend a visit to La Scala. This opera house is rated 4.7 out of 5 stars by 26,219 travelers.

If you’re keen to keep exploring, visit Sforzesco Castle Art Library. This highly recommended sightseeing destination has received an average rating of 4.6 out of 5 stars from 68,714 travelers.

Today is also your chance to spend some time at Parco Sempione. This park is rated an average of 4.6 out of 5 stars by 72,914 travelers.

Embrace the thrill of the open road as you wave goodbye to Milan and set your GPS to Venice. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 55 min. Upon reaching Venice, unwind, observe, and explore. 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 Venice.

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

Locals enjoy eating at Ristorante La Piazza, one of the most recommended restaurants in Venice. This city restaurant has an average rating of 4.7 out of 5 stars from 9,892 customers.

If you have an appetite for something else, check out Farini. Around 4,851 customers have given this fantastic restaurant an average of 4.5 out of 5 stars.

With an average rating of 4.5 out of 5 stars from 4,176 customers, Trattoria Bar Pontini 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.

After an incredible dinner, cap off the night with a glass of beer, cocktail, or any refreshing drink.

If you’re up for classic drinks with a modern flair, consider going to Adagio. Around 621 customers have given this incredible bar an average rating of 4.9 out of 5 stars.

Locals of Venice also enjoy the cocktails at Il Mercante. This place is rated an average of 4.8 out of 5 stars by 666 customers and is one of the best you can experience in the city.

Another top-rated alternative for an expertly crafted celebratory drink is Cantina Do Spade. This bar has an average rating of 4.4 out of 5 stars by 3,120 customers.

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

Wake up to day 3 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Florence, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Venice and Florence.

Take the opportunity to see Rialto Bridge. This attraction has an average rating of 4.7 out of 5 stars from 141,666 visitors.

Teatro La Fenice is another sightseeing hotspot in the area. This opera house has been rated an average of 4.7 out of 5 stars by 10,677 travelers.

Venice is also the home of Piazza San Marco. Around 152,982 people have rated this square an average of 4.7 out of 5 stars.

Another place you’ll want to visit is Doge's Palace, which hosts up to 318,104 visitors every year. With an average rating of 4.7 out of 5 stars from a total of 24,775 reviews, a visit to this palace is a great idea.

This day of your vacation in Venice is also your chance to admire Bridge of Sighs. This must-visit footbridge enjoys an average rating of 4.6 out of 5 stars from 18,223 reviews.

Continue your road trip and head to your next destination, Florence. This car ride takes around 2 hours 54 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 day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Florence. Savor the local cuisine and relax as you recount the day's experiences.

At the top-rated restaurant Ristorante Paoli, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.9 out of 5 stars by 6,031 customers.

If you feel like having something else, Osteria Vecchio Cancello is another great option. This fantastic restaurant has an average rating of 4.8 out of 5 stars by 1,589 customers.

A third restaurant you could check out is Ristorante Oliviero 1962. Ristorante Oliviero 1962 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 1,046 customers speak for itself.

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

When you’ve finished your meal, visit Manifattura for a well-deserved after-dinner drink. One of the best bars in the city, Manifattura has an average rating of 4.7 out of 5 stars from 509 customers.

If you’d rather go to a different spot, Caffe Concerto Paszkowski is another great option. This bar enjoys an average rating of 4.3 out of 5 stars from 4,000 bar-goers.

Ristorante Buca Mario is also a great city bar with a welcoming atmosphere. Ristorante Buca Mario has an average rating of 4.4 out of 5 stars from 1,879 customers.

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.

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence, Bologna, 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 piazza della Signoria. This square is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 66,956 visitors.

Ponte Vecchio is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 118,099 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Uffizi Gallery. Visitors have rated this national museum an average of 4.7 out of 5 stars in 61,794 reviews. Uffizi Gallery receives around 2,011,219 visitors every year.

Bologna’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 32 min. Bologna welcomes you with a multitude of unique vacation experiences.

Make Piazza Maggiore one of your first sightseeing stops in Bologna. Rated an average of 4.7 out of 5 stars by 64,523 travelers, a visit to this local attraction makes for a great introduction to the area.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Milan. Your travel time is around 2 hours 31 min.

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 Milan.

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

According to reviews, Primè is one of the absolute best places to eat in Milan. At this restaurant, you’ll enjoy a great atmosphere and a fantastic food and drinks menu. Primè is rated an average of 4.3 out of 5 stars by 1,184 customers.

Alternatively, if you’re curious to try a local favorite, check out Contraste. This restaurant is rated an average of 4.7 out of 5 stars by 823 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 Nero 9 a visit instead. This restaurant is a top recommendation often mentioned by both travelers and locals. Nero 9 has an average rating of 4.5 out of 5 stars by 573 customers.

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

When an after-dinner drink sounds enticing, visit Kilburn Cocktail Bar Milano, one of the best bars in the city of Milan. This bar has an average rating of 4.5 out of 5 stars from 954 customers.

Get drinks as good as this day's adventure at BhangraBar. Considered one of the most popular bars in the city of Milan, this bar is rated an average of 4 out of 5 stars by 4,036 customers.

Camparino in Galleria is also a great bar where you can have nice chats over delicious bites. Camparino in Galleria has an average rating of 4.4 out of 5 stars from 1,473 customers.

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

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 Milan before saying goodbye.

Make the most of your final day in Italy by visiting Milan’s iconic markets and shopping establishments. Your stay’s proximity to the city’s retail haven invites an unhurried and unforgettable exploration of its variety of stores and establishments.

Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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

For a culinary experience you will remember, have a look at the menu at Bice Restaurant.

If you feel like having something slightly different, check out Ribot Restaurant. Considering its average rating of 4.5 out of 5 stars by 3,991 customers, it’s one that most guests enjoy.

L'immagine Bistrot Ristorante is another restaurant you could book a table at tonight.

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!