Luxury 4-Day Italy Road Trip from Milan traveling south to 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!

Drop by the renowned Rotonda della Besana. This popular sightseeing destination has been rated an average of 4.4 out of 5 stars by 2,614 visitors.

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.

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

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its , this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international and contemporary dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Round off your dining experience by visiting Nottingham Forest, a prime location for a drink. Alternatively, explore the distinctive characteristics of Armani/Bamboo Bar, a bar catering to every mood and preference. Mag Cafe likewise offers a unique atmosphere, perfect for a memorable night out.

Raise a toast to the start of your 4-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. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Duomo di Milano Museum. This art museum is rated an average of 4.8 out of 5 stars from 138,554 visitors. Duomo di Milano Museum welcomes around 341,609 visitors every year.

Galleria Vittorio Emanuele II is another popular attraction you could visit today. This commercial gallery has a rating of 4.7 out of 5 stars from 91,394 visitors.

Sforzesco Castle Art Library is also highly recommended by travelers. This library has a rating of 4.6 out of 5 stars from 68,714 visitors.

Parco Sempione is an attraction you won’t want to miss. This park is rated an average of 4.6 out of 5 stars in 72,914 reviews.

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

Discover a world of culinary delights in Florence, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds , and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to SE·STO on Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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.

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence and Pisa. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Kick off the day at Ponte Vecchio, a top pick for today’s sightseeing. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Today is also your chance to visit piazzale Michelangelo. Piazzale Michelangelo is a square with an average rating of 4.8 out of 5 stars from 77,744 reviews.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 19 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

When you’re ready for some sightseeing, make your way to Leaning Tower of Pisa. This much-appreciated bell tower is rated 4.7 out of 5 stars in 116,882 reviews. Each year, 3,200,000 people visit this site to admire its unique features.

Next up is Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

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.

Following your dinner, dive into the local bar culture at Kilburn Cocktail Bar Milano. Alternatively, go to Bar Frida, the perfect place for those looking to experience the best of the nightlife. Similarly, The Friends Pub Milano provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 4-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.

Maximize your last day in Italy and go on a shopping spree in Milan’s shopping center. This bustling commercial district is conveniently located near your lodging, granting you leisure time to roam and explore its assortment of establishments.

If you love the adrenaline rush of hunting for the best offers and deals in Italy, you’re in for a treat. A variety of goods and gifts await your discovery. Bring a bit of Italy home with you through these charming souvenirs.

Make the most of what's left of your luxury vacation and head out to the stunning Quadrilatero del Silenzio. This extraordinary sightseeing destination and attraction is rated an average of 4.6 out of 5 stars in 135 reviews, and is an excellent choice for your last sightseeing in Milan.

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

If you're in the mood to try something new, consider Palazzo Parigi Hotel & Grand Spa Milano, another top spot with a mouthwatering menu.

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!