Luxury 10-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. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

When you're ready to see some sights, Knights' Square is a great place to start. This square is rated an average 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 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.

Extend your evening after a delightful meal by visiting JEFFER cocktails & friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise a toast to the start of your 10-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.

Begin your sightseeing with a visit to Santa Maria della Spina. This church building is rated an average of 4.5 out of 5 stars in 3,092 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 Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Pisa Cathedral. This cathedral is rated an average of 4.8 out of 5 stars by 8,361 visitors.

When you arrive in Cascine Vecchie, it's time to take a break from the road.

Take the opportunity to see Parco Regionale Migliarino, San Rossore, Massaciuccoli. This attraction has an average rating 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 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.

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

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.

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

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

A top pick for your self-guided sightseeing tour today is piazza del Campo. Previous visitors have rated this square an average of 4.8 out of 5 stars in 64,175 reviews.

Siena Cathedral is a local recommendation that you also can pay a visit today. This domus is rated an average of 4.8 out of 5 stars in 21,656 reviews.

Another attraction you won't want to miss is Fortezza Medicea (Siena). This fortress is rated an average of 4.5 out of 5 stars in 9,835 reviews.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Tivoli. Your travel time is around 2 hours 42 min.

Journey into the unknown at Villa d'Este, a unique attraction awaiting your visit. This remarkable giardino all'italiana has an average rating of 4.7 out of 5 stars from 25,000 reviews. Every year, Villa d'Este welcomes more than 139,855 curious 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 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 Rome for you, so you can check out the menus and make your reservation in advance.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds , and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Following your dinner, dive into the local bar culture at La Botticella of Poggi Giovanni. Alternatively, go to Sant' Eustachio Caffè, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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.

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 3 nights nights remaining.

Start your sightseeing with a visit to Circus Maximus. This circus is rated an average of 4.4 out of 5 stars from 44,741 visitors.

Colosseum is another popular attraction you could visit today. This roman amphitheatre has a rating of 4.7 out of 5 stars from 328,821 visitors. Colosseum attracts up to 7,400,000 visitors every year.

Roman Forum is also highly recommended by travelers. This square has a rating of 4.7 out of 5 stars from 114,450 visitors.

Capitoline Hill is an attraction you won’t want to miss. This hill is rated an average of 4.7 out of 5 stars in 19,557 reviews.

Another attraction you have the opportunity to visit today is Altare della Patria. This architectural structure has received an average rating of 4.8 out of 5 stars from 49,843 travelers. This local favorite gets around 1,683,070 visitors each year.

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.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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

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 2 nights nights remaining.

When you're ready to see some sights, Trevi Fountain is a great place to start. This sculpture is rated an average of 4.8 out of 5 stars by 343,494 visitors.

Another popular attraction you can visit today is Piazza di Spagna. This square has an average rating of 4.7 out of 5 stars from 113,658 travelers.

We also recommend a stop at Spanish Steps. The monumental staircase has been rated an average of 4.5 out of 5 stars by 57,211 visitors.

If you're keen to explore more, consider visiting piazza del Popolo. This square is a popular attraction with an average rating of 4.6 out of 5 stars from 89,807 reviews.

Villa Borghese is another easily accessible place to visit on this day of your trip. Stop by this urban zone of rome, rated 4.6 out of 5 stars in 69,749 reviews, to discover more of what makes it unique.

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.

Esteemed as a restaurant, it features an exceptional menu.

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 1 night nights remaining.

Journey into the unknown at Castel Sant'Angelo, a unique attraction awaiting your visit. This remarkable museum has an average rating of 4.7 out of 5 stars from 72,431 reviews. Every year, Castel Sant'Angelo welcomes more than 918,591 curious visitors.

When you’re ready to continue your sightseeing, Piazza Navona is a recommended place to visit. This square is rated an average of 4.7 out of 5 stars in 158,771 reviews.

Another must-see attraction in Rome is Pantheon. This spectacular roman temple gets over 30,000,000 visitors every year. Rated an average of 4.8 out of 5 stars by 189,682 travelers, this popular tourist destination in Rome offers an experience you will remember.

Largo di Torre Argentina is another popular stop on travelers' itineraries in Rome. This square promises memorable moments of exploring. Other travelers have rated this attraction 4.5 out of 5 stars in 30,433 reviews.

Lastly, don't miss out on Campo de' Fiori. Rated 4.4 out of 5 stars by 51,133 local and international travelers, it's a popular place to visit.

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.

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

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 7 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City and Otricoli. 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.

Journey into the unknown at Sistine Chapel, a unique attraction awaiting your visit. This remarkable chapel has an average rating of 4.7 out of 5 stars from 52,083 reviews.

When you’re ready to continue your sightseeing, Saint Peter's Square is a recommended place to visit. This square is rated an average of 4.8 out of 5 stars in 38,954 reviews.

Another must-see attraction in Vatican City is Vatican Museums. This spectacular art museum gets over 1,612,530 visitors every year. Rated an average of 4.6 out of 5 stars by 133,310 travelers, this popular tourist destination in Vatican City offers an experience you will remember.

Continue your road trip and head to your next destination, Florence. This car ride takes around 2 hours 21 min.

Make Ocriculum Archaeological Park your first stop of the day. Previous visitors have rated this park an average of 4.5 out of 5 stars in 228 reviews.

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

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

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, SE·STO on Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery 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 luxury holiday in Italy has plenty more in store for you.

Day 8 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 Basilica of Santa Croce in Florence. This popular church has been rated an average of 4.7 out of 5 stars by 28,544 visitors.

Another unforgettable place to experience is piazza della Signoria. Rated 4.8 out of 5 stars by 66,956 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Ponte Vecchio. This deck arch bridge has been rated an average of 4.7 out of 5 stars in 118,099 reviews.

Another favorite attraction in the area is Uffizi Gallery, drawing over 2,011,219 yearly visitors. This national museum and popular place of interest enjoys a rating of 4.7 out of 5 stars from 61,794 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.

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.

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

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 9 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.

Start your sightseeing with a visit to Cathedral of Santa Maria del Fiore. This church is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 76,359 visitors.

Galleria dell'Accademia is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 34,429 reviews gives you an idea of other visitors’ experience at this attraction. It’s estimated that around 1,719,645 people visit this national museum every year.

If it’s still bright and early, make your way to Central Market. Visitors have rated this point of interest an average of 4.4 out of 5 stars in 43,100 reviews.

Basilica di Santa Maria Novella, Firenze (FI) is another unique site you can experience today. This attraction is an archive rated an average of 4.7 out of 5 stars in 23,075 reviews.

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

Discover a world of culinary delights in Pisa, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

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

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 10-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.

On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Thanks to your accommodation’s strategic location, the city’s bustling commercial district is only a stone’s throw away, giving you ample time to leisurely explore the area, filled with local shops.

Take time to find the perfect present, reminding you of the charms of Italy. Each store here is brimming with unique finds. These souvenirs will help you treasure your memories of Italy forever.

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 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!