Luxury 11-Day Italy Road Trip from Pisa traveling east to Siena, Rome, and Florence

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!

Start your sightseeing with a visit to Knights' Square. This square is rated an average 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.

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

After enjoying a fulfilling meal, continue your evening at JEFFER cocktails & friends, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Le Parisien Wine Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Las Volta cocktailbar provides an excellent environment for a relaxed and enjoyable evening.

Raise a toast to the start of your 11-day luxury vacation in Italy and look forward to more fantastic days to come!

Wake up to day 2 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 Siena, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Pisa and Cascine Vecchie.

When you’re ready for some sightseeing, make your way to Leaning Tower of Pisa. This much-appreciated bell tower is rated 4.7 out of 5 stars in 116,882 reviews. Each year, 3,200,000 people visit this site to admire its unique features.

Next up is Angelo Caduto. This sightseeing destination has an average rating of 4.5 out of 5 stars from 150 visitors.

Another top sightseeing recommendation is Piazza del Duomo, Pisa. This square has been rated 4.7 out of 5 stars in 104,550 reviews.

Pisa Cathedral is another attraction you have the opportunity to visit today. This cathedral has an average rating of 4.8 out of 5 stars from 8,361 reviews.

Cascine Vecchie welcomes you with a multitude of unique vacation experiences.

When you’re ready for some sightseeing, make your way to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This much-appreciated park is rated 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 Siena.

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

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

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

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 3 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Siena. 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 Siena Cathedral. This domus is rated an average of 4.8 out of 5 stars by 21,656 visitors.

When you’re finished at Siena Cathedral, head to Opera delle Metropolitana. This one-of-a-kind museum is rated an average of 4.2 out of 5 stars in 879 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit piazza del Campo. This square is rated an average of 4.8 out of 5 stars by 64,175 visitors.

If you’re keen to explore more, then consider a visit to Tower of Mangia. This point of interest is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 673 visitors.

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

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

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

Let the evening flow smoothly from dinner to drinks at La Botticella of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Sant' Eustachio Caffè provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

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 4 nights nights remaining.

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

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

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.

Day 5 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 3 nights nights remaining.

Your sightseeing of the day begins at Piazza Navona, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 158,771 reviews.

Next, satisfy your wanderlust at Pantheon. This roman temple has an average rating of 4.8 out of 5 stars from 189,682 travelers. Given the site's popularity, it’s easy to understand why more than 30,000,000 people visit it every year.

Trevi Fountain is another must-visit attraction. This renowned sculpture offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 343,494 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 Piazza di Spagna. This well-loved square boasts a 4.7 out of 5-star rating from 113,658 reviews.

When there’s still energy left for exploring, Spanish Steps awaits. If you’ve been interested in experiencing a monumental staircase, this is a top pick rated 4.5 out of 5 stars by 57,211 previous visitors.

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

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

Day 6 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 2 nights nights remaining.

When you’re ready for some sightseeing, make your way to Roman Forum. This much-appreciated square is rated 4.7 out of 5 stars in 114,450 reviews.

Next up is Colosseum. This roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 visitors. As one of the top places to visit in the city, Colosseum welcomes 7,400,000 visitors annually.

Another top sightseeing recommendation is Basilica di Santa Maria Maggiore. This major basilica has been rated 4.8 out of 5 stars in 27,678 reviews.

Piazza del Popolo is another attraction you have the opportunity to visit today. This square has an average rating of 4.6 out of 5 stars from 89,807 reviews.

To continue your sightseeing, head over to Villa Borghese. This urban zone of rome is rated an average of 4.6 out of 5 stars in 69,749 reviews.

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

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 7 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.

Kick off the day at Circus Maximus, a top pick for today’s sightseeing. This circus is rated an average of 4.4 out of 5 stars in 44,741 reviews.

Today is also your chance to visit Altare della Patria. Altare della Patria is an architectural structure with an average rating of 4.8 out of 5 stars from 49,843 reviews. Attracting more than 1,683,070 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

Largo di Torre Argentina is another top attraction we highly recommend you visit today. This square is rated an average of 4.5 out of 5 stars by 30,433 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Campo de' Fiori. This square is rated an average of 4.4 out of 5 stars by 51,133 visitors.

Lastly, don’t miss out on Castel Sant'Angelo, a famous museum in Rome. This attraction welcomes 918,591 visitors annually and is rated an average of 4.7 out of 5 stars by 72,431 travelers.

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

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.

On day 8 of your luxury holiday in Italy, your road trip route will take you exploring the best of Orvieto. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Orvieto. This drive usually takes around 1 hour 38 min, without any stops or traffic disruptions.

An excellent attraction to start your day with is Orvieto Cathedral. This catholic cathedral is rated an average of 4.8 out of 5 stars in 15,057 reviews.

Continue your journey at Orvieto Underground. This archaeological site is rated 4.6 out of 5 stars by 1,517 travelers from near and far. Approximately 37,000 people come to this place of interest every year to enjoy a unique experience in Orvieto.

Set your GPS to Orvieto and hit the road. Expect a journey of approximately 1 hour 38 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Orvieto beckons with new experiences!

Journey into the unknown at Well of St. Patrick, a unique attraction awaiting your visit. This remarkable sightseeing destination has an average rating of 4.5 out of 5 stars from 14,274 reviews.

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

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

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its , this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to SE·STO on Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery 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 luxury holiday in Italy has plenty more in store for you.

Day 9 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.

Drop by the renowned Ponte Vecchio. This popular deck arch bridge has been rated an average of 4.7 out of 5 stars by 118,099 visitors.

Another unforgettable place to experience is Uffizi Gallery. Rated 4.7 out of 5 stars by 61,794 visitors, this national museum deserves a spot on today's sightseeing itinerary.

We also recommend a visit to piazza della Signoria. This square has been rated an average of 4.8 out of 5 stars in 66,956 reviews.

Another favorite attraction in the area is Basilica of Santa Croce in Florence. This church and popular place of interest enjoys a rating of 4.7 out of 5 stars from 28,544 local and international travelers.

If you’re keen to explore even more, then consider a visit to piazzale Michelangelo. With an average rating of 4.8 out of 5 stars from 77,744 travelers, this square is an attraction many avid travelers highly recommend visiting while in Florence.

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

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

Wake up to day 10 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 Florence.

Kick off the day at Cathedral of Santa Maria del Fiore, a top pick for today’s sightseeing. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Today is also your chance to visit Galleria dell'Accademia. Galleria dell'Accademia is a national museum with an average rating of 4.6 out of 5 stars from 34,429 reviews. Attracting more than 1,719,645 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

Central Market is another top attraction we highly recommend you visit today. This point of interest is rated an average of 4.4 out of 5 stars by 43,100 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Basilica di Santa Maria Novella, Firenze (FI). This archives is rated an average of 4.7 out of 5 stars by 23,075 visitors.

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 Bar Mocambo, known for its inviting atmosphere. Tree is another great option if you’re looking for a place to get the night started. Similarly, Chupiteria provides a great setting to enjoy the night away.

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

Today is the last day of your 11-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 Logge dei Banchi. This extraordinary point of interest and attraction is rated an average of 4.2 out of 5 stars in 1,128 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!