Luxury 5-Day Italy Road Trip from Pisa traveling north to Genoa and Milan

Your luxury holiday in Italy begins as soon as you reach the city of Pisa. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Start your sightseeing with a visit to Knights' Square. This square is a popular stop on travelers’ itineraries in Pisa, with an average rating of 4.5 out of 5 stars by 9,051 visitors.

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

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at JEFFER cocktails & friends, a well-loved spot among locals and tourists. Or, head to Le Parisien Wine Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Las Volta cocktailbar, another top-rated place in the area.

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 Pisa and Cascine Vecchie. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Your sightseeing of the day begins at Palazzo Blu, a remarkable art museum where it’s easy to get lost in exploration. This top attraction is rated an average of 4.5 out of 5 stars in 4,244 reviews. Each year, this popular place of interest welcomes approximately 37,457 visitors.

Next, satisfy your wanderlust at Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 travelers. Given the site's popularity, it’s easy to understand why more than 3,200,000 people visit it every year.

Piazza del Duomo, Pisa is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 104,550 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 Pisa Cathedral. This well-loved cathedral boasts a 4.8 out of 5-star rating from 8,361 reviews.

Set your GPS to Cascine Vecchie and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cascine Vecchie beckons with new experiences!

Journey into the unknown at Parco Regionale Migliarino, San Rossore, Massaciuccoli, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.4 out of 5 stars from 9,632 reviews.

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

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

Get ready for an unforgettable culinary journey in Genoa by reserving a table at The Cook. Renowned as a 1-star Michelin restaurant, it offers an exceptional modern menu. For a different taste experience, head to San Giorgio, recognized for its delicious modern and ligurian dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Marin, a local favorite known for its delightful seafood and contemporary cuisine in Genoa. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning seafood and contemporary foodies seeking culinary excellence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Scurreria Beer & Bagel, known for its inviting atmosphere. La Lepre is another great option if you’re looking for a place to get the night started.

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 Genoa and Monza.

Begin your sightseeing with a visit to piazza De Ferrari. This extraordinary square is rated an average of 4.6 out of 5 stars by 34,312 visitors.

Next, make your way to Via Garibaldi. This top attraction is a sightseeing destination with an average rating of 4.6 out of 5 stars by 5,399 visitors.

We also recommend a visit to Aquarium of Genoa. Hosting 1,200,000 visitors every year, Aquarium of Genoa is one of the most popular places to visit in Genoa. This public aquarium is rated 4.5 out of 5 stars by 62,259 travelers.

Fasten your seatbelt and make your way to your next stop. Monza, 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 Genoa to Monza may take around 2 hours 9 min without traffic disruptions. Upon arrival in Monza, we highly recommend checking out some of the top attractions.

A top pick for your self-guided sightseeing tour today is Monza Circuit. Previous visitors have rated this motorsport racing track an average of 4.6 out of 5 stars in 14,877 reviews.

Monza Park is a local recommendation that you also can pay a visit today. This park is rated an average of 4.7 out of 5 stars in 34,629 reviews.

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.

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

If you’re not ready to end the night just yet, Nottingham Forest offers a perfect venue to relax and savor a drink. Similarly, Armani/Bamboo Bar is well-suited for those looking to unwind in a social setting. Mag Cafe is another excellent spot to enjoy a nightcap after a delightful meal.

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 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan and Sarzana. 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 Duomo di Milano Museum. This art museum is a popular stop on travelers’ itineraries in Milan, with an average rating of 4.8 out of 5 stars by 138,554 visitors. Around 341,609 people visit this attraction every year.

Galleria Vittorio Emanuele II is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 91,394 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Parco Sempione. Visitors have rated this park an average of 4.6 out of 5 stars in 72,914 reviews.

As you’ve unraveled the marvels of Milan, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Sarzana may take around 2 hours 44 min. Upon your arrival in Sarzana, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready to see some sights, Fortezza di Firmafede is a great place to start. This citadel is rated an average of 4.4 out of 5 stars by 1,796 visitors. Fortezza di Firmafede attracts more than 3,765 visitors every year.

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

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 Pisa for you, so you can check out the menus and make your reservation in advance.

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

Extend your evening after a delightful meal by visiting Bar Mocambo, which offers the perfect atmosphere for a night out. Moreover, Tree is another popular option for a drink or two. Likewise, Chupiteria also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 Pisa before saying goodbye.

As your final day in Italy unfolds, don’t miss the chance for a last-minute shopping spree in Pisa’s best shopping location. Your accommodation’s convenient location near the city’s shopping area offers the luxury of time, so you don’t have to limit yourself from leisurely strolling its streets amidst a collection of establishments.

Look for the perfect gift for your loved ones back home, or buy yourself a little keepsake to remind you of Italy. Keep the spirit of your trip to Italy alive with these special souvenirs.

Make the most of what's left of your luxury vacation and head out to the stunning “Tuttomondo” (Keith Haring). This extraordinary sightseeing destination and attraction is rated an average of 4.6 out of 5 stars in 1,937 reviews, and is an excellent choice for your last sightseeing in Pisa.

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

If you're in the mood to try something new, consider Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. , another top spot with a mouthwatering menu.

You will then say farewell to Pisa 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!