Luxury 4-Day Italy Road Trip from Pisa traveling west to 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!

Make Knights' Square your first stop of the day. Previous visitors have rated this square an average of 4.5 out of 5 stars in 9,051 reviews.

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

Continue the enjoyment post-dinner at JEFFER cocktails & friends, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Le Parisien Wine Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Las Volta cocktailbar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise a toast to the start of your 4-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 Pisa and Cascine Vecchie. 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 del Duomo, Pisa. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.

Next up, make your way to Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 reviews. Usually, around 3,200,000 people visit Leaning Tower of Pisa every year.

When you’re ready for your next sight of the day, continue to Pisa Cathedral. This cathedral has an average rating of 4.8 out of 5 stars from 8,361 visitors.

Start your sightseeing with a visit to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This park is rated an average of 4.4 out of 5 stars from 9,632 visitors.

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

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

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and modern foodies seeking culinary excellence.

Let the evening flow smoothly from dinner to drinks at Nottingham Forest, a top-rated bar in the area. For other recommendations, Armani/Bamboo Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Mag Cafe offers a memorable night with diverse drink options and excellent service.

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.

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

When you're ready to see some sights, Galleria Vittorio Emanuele II is a great place to start. This commercial gallery is rated an average of 4.7 out of 5 stars by 91,394 visitors.

Another popular attraction you can visit today is Sforzesco Castle Art Library. This library has an average rating of 4.6 out of 5 stars from 68,714 travelers.

We also recommend a stop at Parco Sempione. The park has been rated an average of 4.6 out of 5 stars by 72,914 visitors.

If you're keen to explore more, consider visiting Piazza Gae Aulenti. This square is a popular attraction with an average rating of 4.6 out of 5 stars from 30,398 reviews.

Duomo di Milano Museum is another easily accessible place to visit on this day of your trip. Stop by this art museum, rated 4.8 out of 5 stars in 138,554 reviews, to discover more of what makes it unique. This attraction gets 341,609 visitors every year.

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

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

Esteemed as a restaurant, it features an exceptional menu.

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

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.

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 Pisa before saying goodbye.

Make the most of your final day in Italy by visiting Pisa’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 “Tuttomondo” (Keith Haring). This extraordinary point of interest 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 eager to try something different, consider Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. , another top spot with a tantalizing 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!