Luxury 6-Day Italy Road Trip from Pisa to Milan, Bologna, and Rome and surrounding area

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

Seize the day by visiting some of the best attractions in the area, like Knights' Square. This extraordinary square has an average rating of 4.5 out of 5 stars from 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.

As a top-rated it is an ideal choice in the city.

Continue your evening by exploring the vibrant nightlife scene at JEFFER cocktails & friends, a prime destination for a thrilling night out. Also, don’t forget to check out Le Parisien Wine Bar, a bar that offers unique local touches. Likewise, Las Volta cocktailbar provides an excellent alternative for a fun evening.

Raise a toast to the start of your 6-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.

Take the opportunity to see Piazza del Duomo, Pisa. This attraction has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Leaning Tower of Pisa is another sightseeing hotspot in the area. This bell tower has been rated an average of 4.7 out of 5 stars by 116,882 travelers. Up to 3,200,000 people visit Leaning Tower of Pisa every year.

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.

Admire the views and listen to some good music as you drive in the direction of Cascine Vecchie.

Kick off the day at Parco Regionale Migliarino, San Rossore, Massaciuccoli, a top pick for today’s sightseeing. This park is rated an average of 4.4 out of 5 stars in 9,632 reviews.

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

Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Milan.

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Il Luogo Aimo e Nadia, a top-rated restaurant known for its outstanding menu. Known as a top-rated , it's a top choice for italian contemporary and modern cuisine in the city.

To truly maximize your evening out, consider visiting Nottingham Forest after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Armani/Bamboo Bar, another bar with an inviting ambiance. Similarly, Mag Cafe 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 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 Milan. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Seize the day by visiting some of the best attractions in the area, like Galleria Vittorio Emanuele II. This extraordinary commercial gallery has an average rating of 4.7 out of 5 stars from 91,394 visitors.

Next, make your way to Sforzesco Castle Art Library. This library is rated an average of 4.6 out of 5 stars in 68,714 reviews.

While in Milan, we also recommend a visit to Parco Sempione. This park has been rated an average of 4.6 out of 5 stars in 72,914 reviews.

If you’re keen to explore even more, then consider a visit to Piazza Gae Aulenti. With an average rating of 4.6 out of 5 stars by 30,398 travelers, this square is a highly recommended stop on your sightseeing around Milan.

Make your way to Duomo di Milano Museum, perhaps the most famous art museum in Milan. This attraction welcomes around 341,609 visitors annually and is rated an average of 4.8 out of 5 stars in 138,554 reviews.

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

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

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 fulfilling meal, continue your evening at Bar Freud e Squisito, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Osteria del Sole offers a welcoming atmosphere for easing into the nightlife. Similarly, Macondo - Cocktail Bar provides an excellent environment for a relaxed and enjoyable evening.

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

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 Rome, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Casalecchio di Reno and Roncobilaccio.

As you’ve unraveled the marvels of Bologna, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Casalecchio di Reno may take around 29 min. Upon your arrival in Casalecchio di Reno, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Journey into the unknown at Parco della Chiusa, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.6 out of 5 stars from 2,583 reviews.

When you’re ready to continue your sightseeing, Parco Talon is a recommended place to visit. This park is rated an average of 4.7 out of 5 stars in 2,343 reviews.

Fasten your seatbelt and make your way to your next stop. Roncobilaccio, 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 Casalecchio di Reno to Roncobilaccio may take around 49 min without traffic disruptions. Upon arrival in Roncobilaccio, we highly recommend checking out some of the top attractions.

Start your sightseeing with a visit to Sanctuary of Madonna of Bocca of Rio. This church is a popular stop on travelers’ itineraries in Roncobilaccio, with an average rating of 4.7 out of 5 stars by 1,828 visitors.

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

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

Dive into a culinary adventure like no other in Rome by booking a table at La Pergola. This popular restaurant holds , and offers an exceptional menu of mediterranean and contemporary cuisine. For another culinary dining option, venture to Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Enoteca La Torre, a top local restaurant known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Explore the vibrant nightlife at La Botticella of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Sant' Eustachio Caffè for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino 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.

Wake up to day 5 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Rome. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Begin your sightseeing with a visit to Roman Forum. This extraordinary square is rated an average of 4.7 out of 5 stars by 114,450 visitors.

Next, make your way to Colosseum. This top attraction is a roman amphitheatre with an average rating of 4.7 out of 5 stars by 328,821 visitors. Colosseum welcomes 7,400,000 yearly visitors.

We also recommend a visit to Trevi Fountain. This sculpture is rated 4.8 out of 5 stars by 343,494 travelers.

If you’re keen to keep exploring, visit Foro Italico. This highly recommended sightseeing destination has received an average rating of 4.6 out of 5 stars from 25,438 travelers.

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.

This renowned restaurant holds , and offers an exceptional menu of cuisine.

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

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 6-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.

Esteemed as a restaurant, it features an exceptional menu. If you're in the mood for something new, try Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. , another premier location with a delectable 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!