Luxury 9-Day Italy Road Trip from Pisa to Siena, Rome, Florence, Venice, and Milan and surrounding area

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!

Drop by the renowned Logge dei Banchi. This popular sightseeing destination has been rated an average of 4.2 out of 5 stars by 1,128 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.

In Pisa, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.

After your meal, keep the night alive at a bar like JEFFER cocktails & friends, known for its lively atmosphere. Le Parisien Wine Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Las Volta cocktailbar offers an excellent atmosphere for those looking to amp up the 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 Pisa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

When you’re ready for some sightseeing, make your way to Museo dell'Opera del Duomo. This much-appreciated museum is rated 4.6 out of 5 stars in 418 reviews.

Next up is Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 visitors. As one of the top places to visit in the city, Leaning Tower of Pisa welcomes 3,200,000 visitors annually.

Another top sightseeing recommendation is Pisa Cathedral. This cathedral has been rated 4.8 out of 5 stars in 8,361 reviews.

Piazza del Duomo, Pisa is another attraction you have the opportunity to visit today. This square has an average rating of 4.7 out of 5 stars from 104,550 reviews.

To continue your sightseeing, head over to Campo santo. This cemetery is rated an average of 4.6 out of 5 stars in 586 reviews.

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

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

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Fasten your seatbelt and make your way to your next stop. Vatican City, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Drop by the renowned Sistine Chapel. This popular chapel has been rated an average of 4.7 out of 5 stars by 52,083 visitors.

Another unforgettable place to experience is St. Peter's Basilica. Rated 4.8 out of 5 stars by 131,043 visitors, this major basilica deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Saint Peter's Square. This square has been rated an average of 4.8 out of 5 stars in 38,954 reviews.

Another favorite attraction in the area is Vatican Museums, drawing over 1,612,530 yearly visitors. This art museum and popular place of interest enjoys a rating of 4.6 out of 5 stars from 133,310 local and international travelers.

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

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

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended restaurant in Rome is Enoteca La Torre, a renowned restaurant , known for its delicious mediterranean and creative menu.

Round off your dining experience by visiting La Botticella of Poggi Giovanni, a prime location for a drink. Alternatively, explore the distinctive characteristics of Sant' Eustachio Caffè, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 4 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 1 night nights remaining.

Your sightseeing of the day begins at Colosseum, a remarkable roman amphitheatre where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 328,821 reviews. Each year, this popular place of interest welcomes approximately 7,400,000 visitors.

Next, satisfy your wanderlust at Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 travelers.

Pantheon is another must-visit attraction. This renowned roman temple offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 189,682 travelers and attracting 30,000,000 annual visitors, 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 Piazza Navona. This well-loved square boasts a 4.7 out of 5-star rating from 158,771 reviews.

When there’s still energy left for exploring, Castel Sant'Angelo awaits. If you’ve been interested in experiencing a museum, this is a top pick rated 4.7 out of 5 stars by 72,431 previous visitors. Each year, approximately 918,591 people travel to Rome to experience it.

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.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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

Make Altare della Patria one of your first sightseeing stops in Rome. Rated an average of 4.8 out of 5 stars by 49,843 travelers, a visit to this local attraction makes for a great introduction to the area. This architectural structure attracts 1,683,070 visitors every year.

Trevi Fountain is a worthwhile attraction you can visit next. This sculpture is a valued place of interest in the area, with an average rating of 4.8 out of 5 stars from 343,494 reviews.

Today is also the perfect opportunity to drop by Piazza di Spagna. This square has been rated an average of 4.7 out of 5 stars by 113,658 visitors.

If you’re keen to explore more, head to piazza del Popolo. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 89,807 previous visitors.

Another top place to visit is Villa Borghese. This urban zone of rome enjoys an average rating of 4.6 out of 5 stars from 69,749 local and international travelers.

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

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

Start your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds , 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. SE·STO on Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery 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 6 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Be one of the day’s first visitors at piazza della Signoria. This square is rated an average of 4.8 out of 5 stars by 66,956 visitors.

When you’re finished at piazza della Signoria, head to Cathedral of Santa Maria del Fiore. This one-of-a-kind church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza della Repubblica. This square is rated an average of 4.6 out of 5 stars by 22,356 visitors.

If you’re keen to explore more, then consider a visit to Ponte Vecchio. This deck arch bridge is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 118,099 visitors.

To round off your sightseeing experience, make your way to piazzale Michelangelo. This famous square 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 Venice.

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

Experience a taste of local culinary excellence while in Venice by securing a table at Local. Esteemed as a 1-star Michelin restaurant, it features an exceptional contemporary menu. For an alternative taste experience, visit Wistèria, famous for its scrumptious contemporary and venetian dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Quadri, a local favorite celebrated for its exquisite modern cuisine in Venice. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for modern cuisine lovers seeking top-notch culinary experiences.

Keep the excitement of the evening going by going to a bar or two. Al Parlamento is an excellent place to start. You could also check out Adagio, offering a different kind of charm. A last recommendation for the day is Il Mercante. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise a toast to another amazing day of your luxury holiday in Florence, 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.

Seize the day by visiting some of the best attractions in the area, like Rialto Bridge. This extraordinary stone bridge has an average rating of 4.7 out of 5 stars from 141,666 visitors.

Next, make your way to Piazza San Marco. This square is rated an average of 4.7 out of 5 stars in 152,982 reviews.

While in Venice, we also recommend a visit to St Mark's Basilica. This cathedral has been rated an average of 4.7 out of 5 stars in 18,439 reviews.

If you’re keen to explore even more, then consider a visit to Doge's Palace. This attraction gets around 318,104 yearly visitors. With an average rating of 4.7 out of 5 stars by 24,775 travelers, this palace is a highly recommended stop on your sightseeing around Venice.

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.

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated it is an ideal choice for italian contemporary and modern cuisine in the city.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Nottingham Forest, a well-loved spot among locals and tourists. Or, head to Armani/Bamboo Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Mag Cafe, 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 Pisa, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Milan and Genoa.

Your sightseeing of the day begins at Cathedral Square, a remarkable point of interest where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 7,539 reviews.

Next, satisfy your wanderlust at Galleria Vittorio Emanuele II. This commercial gallery has an average rating of 4.7 out of 5 stars from 91,394 travelers.

Duomo di Milano Museum is another must-visit attraction. This renowned art museum offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 138,554 travelers and attracting 341,609 annual visitors, it's one of the more popular places to see in the area.

Fasten your seatbelt and make your way to your next stop. Genoa, 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 Milan to Genoa may take around 1 hour 58 min without traffic disruptions. Upon arrival in Genoa, we highly recommend checking out some of the top attractions.

A top pick for your self-guided sightseeing tour today is Spiaggia Pubblica di Priaruggia. 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 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.

After enjoying a fulfilling meal, continue your evening at Bar Mocambo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tree offers a welcoming atmosphere for easing into the nightlife. Similarly, Chupiteria provides an excellent environment for a relaxed and enjoyable evening.

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 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 Pisa before saying goodbye.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Pisa’s celebrated shopping district. Thanks to your stay’s premier location, you can easily visit the city’s commercial hubs and wander through its diverse range of local shops without rushing.

Whether you’re on a hunt for an ideal present to give to your friends or family or looking for a personal memento to remind you of Italy, a variety of items are waiting for you. Hold onto the magic of Italy with these wonderful souvenirs, ensuring your memories never fade.

Make the most of what's left of your luxury vacation and head out to the stunning Knights' Square. This extraordinary square and attraction is rated an average of 4.5 out of 5 stars in 9,051 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.

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!