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

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!

Kick off the day at Central Market, a top pick for today’s sightseeing. This point of interest is rated an average of 4.4 out of 5 stars in 43,100 reviews.

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.

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.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffe San Firenze is another top choice with a popular menu. You could also check for a table at Ditta Artigianale. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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. The day's journey will conclude in Venice, 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.

Begin your sightseeing with a visit to Piazza Della Signoria. This extraordinary square is rated an average of 4.8 out of 5 stars by 66,956 visitors.

Next, make your way to Uffizi Gallery. This top attraction is a national museum with an average rating of 4.7 out of 5 stars by 61,794 visitors. Uffizi Gallery welcomes 2,011,219 yearly visitors.

We also recommend a visit to Ponte Vecchio. This deck arch bridge is rated 4.7 out of 5 stars by 118,099 travelers.

If you’re keen to keep exploring, visit Cathedral Of Santa Maria Del Fiore. This highly recommended sightseeing destination has received an average rating of 4.8 out of 5 stars from 76,359 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Venice. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Experience a symphony of flavors at Local in Venice by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Local delights its guests with its exceptional variety of meals showcasing delicious contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Wistèria, acclaimed for its delectable contemporary, and venetian specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Quadri, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for modern cuisine in the city.

Following your dinner, dive into the local bar culture at Al Parlamento. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Adagio, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Mercante provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 Milan, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Venice.

Make Rialto Bridge one of your first sightseeing stops in Venice. Rated an average of 4.7 out of 5 stars by 141,666 travelers, a visit to this local attraction makes for a great introduction to the area.

Teatro La Fenice is a worthwhile attraction you can visit next. This opera house is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 10,677 reviews.

Today is also the perfect opportunity to drop by Piazza San Marco. This square has been rated an average of 4.7 out of 5 stars by 152,982 visitors.

If you’re keen to explore more, head to Doge's Palace and find out why 318,104 people visit this spot every year. A trip to this popular palace is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 24,775 previous visitors.

Another top place to visit is Bridge Of Sighs. This footbridge enjoys an average rating of 4.6 out of 5 stars from 18,223 local and international travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

After a long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Milan for you, so you can check out the menus and make your reservation in advance.

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international, and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary, and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Continue your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun evening.

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.

Wake up to day 4 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Milan, and Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Seize the day by visiting some of the best attractions in the area, like Cathedral Square. This extraordinary sightseeing destination has an average rating of 4.8 out of 5 stars from 7,539 visitors.

Next, make your way to Galleria Vittorio Emanuele Ii. This commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

While in Milan, we also recommend a visit to Duomo Di Milano Museum. Hosting around 341,609 visitors every year, Duomo Di Milano Museum is one of the best places to visit. This art museum has been rated an average of 4.8 out of 5 stars in 138,554 reviews.

Bologna’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Milan behind. This drive usually takes around 2 hours 28 min. Bologna welcomes you with a multitude of unique vacation experiences.

Begin your sightseeing with a visit to Piazza Maggiore. This extraordinary square is rated an average of 4.7 out of 5 stars by 64,523 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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.

Start your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative, and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary, and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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.

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.

On your last day in Italy, take time to indulge in shopping at Florence’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Make the most of what's left of your luxury vacation and head out to the stunning Piazzale Michelangelo. This extraordinary square and attraction is rated an average of 4.8 out of 5 stars in 77,744 reviews, and is an excellent choice for your last sightseeing in Florence.

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

Enjoy a lovely meal at Tijuana, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Djària - American Bar is another top choice with a popular menu.

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!