Luxury 9-Day Italy Road Trip from Perugia traveling north to Florence, Pisa, Milan, Venice, and Bologna

Your luxury holiday in Italy begins as soon as you reach the city of Perugia, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Begin your sightseeing with a visit to Piazza IV Novembre. This extraordinary square is rated an average of 4.6 out of 5 stars by 9,189 visitors.

Tonight, you will be treated to a stay at one of the best luxury hotels in Perugia. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

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 Perugia for you so you can browse their menus in advance and make a reservation.

With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Tommi Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Valentina offers an ideal atmosphere to enjoy the pleasures of the night. Caffe Dal Perugino is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to the start of your 9-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 Perugia and Magione. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Frontone Gardens. This garden is rated an average of 4.4 out of 5 stars from 1,722 visitors.

Carducci Gardens is another popular attraction you could visit today. This park has a rating of 4.5 out of 5 stars from 1,768 visitors.

Chiesa di San Michele Arcangelo is also highly recommended by travelers. This church has a rating of 4.8 out of 5 stars from 926 visitors.

Rocca Paolina is an attraction you won’t want to miss. This rocca is rated an average of 4.7 out of 5 stars in 7,128 reviews.

Upon your arrival in Magione, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Begin your sightseeing with a visit to Parco Regionale del Lago Trasimeno. This park is rated an average of 4.4 out of 5 stars in 8,831 reviews.

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

After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Florence. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. Esteemed as a 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, SE·STO on Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence. 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 piazza della Signoria, a top pick for today’s sightseeing. This square is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Today is also your chance to visit Cathedral of Santa Maria del Fiore. Cathedral of Santa Maria del Fiore is a church with an average rating of 4.8 out of 5 stars from 76,359 reviews.

Ponte Vecchio is another top attraction we highly recommend you visit today. This deck arch bridge is rated an average of 4.7 out of 5 stars by 118,099 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Uffizi Gallery. This national museum is rated an average of 4.7 out of 5 stars by 61,794 visitors. Visiting Uffizi Gallery means you'll be one of 2,011,219 people who do so every year.

Lastly, don’t miss out on piazzale Michelangelo, a famous square in Florence. This attraction is rated an average of 4.8 out of 5 stars by 77,744 travelers.

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

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 Pisa. Savor the local cuisine and relax as you recount the day's experiences.

After your delicious meal, get a taste of the vibrant nightlife with a visit to JEFFER cocktails & friends, known for its inviting atmosphere. Le Parisien Wine Bar is another great option if you’re looking for a place to get the night started. Similarly, Las Volta cocktailbar provides a great setting to enjoy the night away.

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 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 2 nights. The day's itinerary unfolds with a diverse array of experiences in Pisa and Genoa.

Take the opportunity to see Leaning Tower of Pisa. This attraction has an average rating of 4.7 out of 5 stars from 116,882 visitors and gets around 3,200,000 visits every year.

Piazza del Duomo, Pisa is another sightseeing hotspot in the area. This square has been rated an average of 4.7 out of 5 stars by 104,550 travelers.

Pisa is also the home of Pisa Cathedral. Around 8,361 people have rated this cathedral an average of 4.8 out of 5 stars.

Embrace the thrill of the open road as you wave goodbye to Pisa and set your GPS to Genoa. 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 1 hour 43 min. Upon reaching Genoa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Make Spiaggia Pubblica di Priaruggia your first stop of the day. Previous visitors have rated this point of interest an average of 4.3 out of 5 stars in 2,161 reviews.

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

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.

Have a memorable dining experience in Milan by booking a table at Enrico Bartolini al Mudec, renowned as a 3-star Michelin restaurant presenting an exceptional creative menu. For a different culinary experience, Seta by Antonio Guida shines as one of the top destinations known for its delicious international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Il Luogo Aimo e Nadia is known as a top local spot for its delicious italian contemporary and modern cuisine in Milan. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Explore the vibrant nightlife at Nottingham Forest after your meal, a hub for lively evenings and memorable moments. Or, head to Armani/Bamboo Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Mag Cafe is perfect for those looking to extend their night with a touch of local flavor.

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.

Day 5 of your luxury road trip in Italy begins and concludes in the city of Milan. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Milan, where you still have 1 night nights remaining.

Drop by the renowned Duomo di Milano Museum. This popular art museum has been rated an average of 4.8 out of 5 stars by 138,554 visitors. Based on recent data, this attraction is visited by more than 341,609 travelers every year.

Another unforgettable place to experience is Galleria Vittorio Emanuele II. Rated 4.7 out of 5 stars by 91,394 visitors, this commercial gallery deserves a spot on today's sightseeing itinerary.

We also recommend a visit to La Scala. This opera house has been rated an average of 4.7 out of 5 stars in 26,219 reviews.

Another favorite attraction in the area is Sforzesco Castle Art Library. This library and popular place of interest enjoys a rating of 4.6 out of 5 stars from 68,714 local and international travelers.

If you’re keen to explore even more, then consider a visit to Parco Sempione. With an average rating of 4.6 out of 5 stars from 72,914 travelers, this park is an attraction many avid travelers highly recommend visiting while in Milan.

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.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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

Wake up to day 6 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Valeggio sul Mincio and Verona. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Continue your road trip and head to your next destination, Valeggio sul Mincio. This car ride takes around 2 hours 3 min.

Begin your sightseeing with a visit to Parco Giardino Sigurtà. This park is rated an average of 4.6 out of 5 stars in 27,387 reviews.

Set your GPS to Verona and hit the road. Expect a journey of approximately 48 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Verona beckons with new experiences!

Seize the day by visiting some of the best attractions in the area, like Castelvecchio Bridge. This extraordinary arch bridge has an average rating of 4.7 out of 5 stars from 12,156 visitors.

Next, make your way to Castelvecchio Museum. This art museum welcomes around 35,031 visitors yearly and is rated an average of 4.6 out of 5 stars in 13,854 reviews.

While in Verona, we also recommend a visit to Verona Arena. Hosting around 195,540 visitors every year, Verona Arena is one of the best places to visit. This opera house has been rated an average of 4.7 out of 5 stars in 123,818 reviews.

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.

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 , it's a top choice for modern cuisine in the city.

If you’re not ready to end the night just yet, Al Parlamento offers a perfect venue to relax and savor a drink. Similarly, Adagio is well-suited for those looking to unwind in a social setting. Il Mercante is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 7 of your luxury holiday in Italy, your road trip route will take you exploring the best of Venice. 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 Rialto Bridge. This stone bridge is rated an average of 4.7 out of 5 stars in 141,666 reviews.

Next up, make your way to Piazza San Marco. This square has an average rating of 4.7 out of 5 stars from 152,982 reviews.

When you’re ready for your next sight of the day, continue to St Mark's Basilica. This cathedral has an average rating of 4.7 out of 5 stars from 18,439 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Doge's Palace. This palace is rated an average of 4.7 out of 5 stars by 24,775 visitors. Visiting Doge's Palace means you'll be one of 318,104 people who do so every year.

If you’re keen to explore even more, then consider a visit to Bridge of Sighs. This footbridge is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 18,223 visitors.

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

Discover a world of culinary delights in Bologna, 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.

Begin your culinary exploration in Bologna by securing a reservation at I Portici. This renowned restaurant offers an exceptional menu of creative and contemporary cuisine. For another dining delight, visit Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Freud e Squisito, a well-loved spot among locals and tourists. Or, head to Osteria del Sole. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Macondo - Cocktail Bar, another top-rated place in the area.

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.

Wake up to day 8 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 Perugia, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Bologna and Siena.

Make Piazza Maggiore your first stop of the day. Previous visitors have rated this square an average of 4.7 out of 5 stars in 64,523 reviews.

Next up, make a stop at Two Towers. With an average rating of 4.7 out of 5 stars by 25,975 visitors, it's easy to understand why so many people visit this tower every year.

Continue your road trip and head to your next destination, Siena. This car ride takes around 2 hours 27 min.

A top pick for your self-guided sightseeing tour today is Siena Cathedral. Previous visitors have rated this domus an average of 4.8 out of 5 stars in 21,656 reviews.

Piazza del Campo is a local recommendation that you also can pay a visit today. This square is rated an average of 4.8 out of 5 stars in 64,175 reviews.

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

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

Keep the excitement of the evening going by going to a bar or two. Caffè Fortebraccio is an excellent place to start. You could also check out Caffe Del Banco, offering a different kind of charm. A last recommendation for the day is Dempsey's Perugia. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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 Perugia before saying goodbye.

Make the most of your final day in Italy by visiting Perugia’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. Take home a piece of Italy with these souvenirs, keeping your adventures close.

Make the most of what's left of your luxury vacation and head out to the stunning Etruscan Arch. This extraordinary architectural element and attraction is rated an average of 4.7 out of 5 stars in 1,190 reviews, and is an excellent choice for your last sightseeing in Perugia.

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

Treat yourself to a delicious dinner at Sangallo Palace Hotel, an excellent option for tonight's dining. Looking for something different? Osteria a Priori offers a tantalizing alternative with its diverse menu. And don’t miss La Bottega di Perugia.

You will then say farewell to Perugia 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!