Luxury 9-Day Italy Road Trip from Pisa traveling south to Florence and Rome

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!

Journey into the unknown at Knights' Square, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.5 out of 5 stars from 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 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.

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

Unwind after your meal by stepping into JEFFER cocktails & friends. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Le Parisien Wine Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Las Volta cocktailbar, another top-rated bar in the area.

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.

Begin your sightseeing with a visit to “Tuttomondo” (Keith Haring). This extraordinary sightseeing destination is rated an average of 4.6 out of 5 stars by 1,937 visitors.

Next, make your way to Leaning Tower of Pisa. This top attraction is a bell tower with an average rating of 4.7 out of 5 stars by 116,882 visitors. Leaning Tower of Pisa welcomes 3,200,000 yearly visitors.

We also recommend a visit to Angelo Caduto. This point of interest is rated 4.5 out of 5 stars by 150 travelers.

If you’re keen to keep exploring, visit Piazza del Duomo, Pisa. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 104,550 travelers.

Today is also your chance to spend some time at Pisa Cathedral. This cathedral is rated an average of 4.8 out of 5 stars by 8,361 travelers.

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

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

Experience a harmony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Known for its 3-star Michelin status, Enoteca Pinchiorri offers a delightful variety of dishes highlighting its delicious italian contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Santa Elisabetta, a highly recommended restaurant known for its enticing creative and mediterranean cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Gucci Osteria da Massimo Bottura, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and international menu.

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.

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 3 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.

Journey into the unknown at Central Market, a unique attraction awaiting your visit. This remarkable sightseeing destination has an average rating of 4.4 out of 5 stars from 43,100 reviews.

When you’re ready to continue your sightseeing, Cathedral of Santa Maria del Fiore is a recommended place to visit. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Another must-see attraction in Florence is Galleria dell'Accademia. This spectacular national museum gets over 1,719,645 visitors every year. Rated an average of 4.6 out of 5 stars by 34,429 travelers, this popular tourist destination in Florence offers an experience you will remember.

Piazzale Michelangelo is another popular stop on travelers' itineraries in Florence. This square promises memorable moments of exploring. Other travelers have rated this attraction 4.8 out of 5 stars in 77,744 reviews.

Lastly, don't miss out on The Boboli Gardens. Rated 4.2 out of 5 stars by 25,341 local and international travelers, it's a popular place to visit.

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 Florence for you, so you can check out the menus and make your reservation in advance.

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

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 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 4 nights. The day's itinerary unfolds with a diverse array of experiences in Florence and Siena.

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 Uffizi Gallery. This one-of-a-kind national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. Every year, approximately 2,011,219 travelers come here to experience the national museum for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars by 118,099 visitors.

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 8 min.

When you’re ready for some sightseeing, make your way to piazza del Campo. This much-appreciated square is rated 4.8 out of 5 stars in 64,175 reviews.

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.

Continue your evening by exploring the vibrant nightlife scene at La Botticella of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Sant' Eustachio Caffè, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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 3 nights nights remaining.

An excellent attraction to start your day with is Circus Maximus. This circus is rated an average of 4.4 out of 5 stars in 44,741 reviews.

Continue your journey at Pantheon. This roman temple is rated 4.8 out of 5 stars by 189,682 travelers from near and far. Approximately 30,000,000 people come to this place of interest every year to enjoy a unique experience in Rome.

Rome is also the home of Piazza Navona. This square has an average rating of 4.7 out of 5 stars from 158,771 visitors.

You can continue your self-guided sightseeing tour at Campo de' Fiori. Rated 4.4 out of 5 stars by 51,133 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Castel Sant'Angelo. With an average rating of 4.7 out of 5 stars from 72,431 reviews, it’s hard to refuse the opportunity to see this museum. Approximately 918,591 people visit this attraction every year.

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.

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

After savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

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

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.

Your sightseeing of the day begins at Trevi Fountain, a remarkable sculpture where it’s easy to get lost in exploration. This top attraction is rated an average of 4.8 out of 5 stars in 343,494 reviews.

Next, satisfy your wanderlust at Piazza di Spagna. This square has an average rating of 4.7 out of 5 stars from 113,658 travelers.

Spanish Steps is another must-visit attraction. This renowned monumental staircase offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.5 out of 5 stars by 57,211 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 del Popolo. This well-loved square boasts a 4.6 out of 5-star rating from 89,807 reviews.

When there’s still energy left for exploring, Villa Borghese awaits. If you’ve been interested in experiencing an urban zone of rome, this is a top pick rated 4.6 out of 5 stars by 69,749 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 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.

When you’re ready for some sightseeing, make your way to largo di Torre Argentina. This much-appreciated square is rated 4.5 out of 5 stars in 30,433 reviews.

Next up is Altare della Patria. This architectural structure has an average rating of 4.8 out of 5 stars from 49,843 visitors. As one of the top places to visit in the city, Altare della Patria welcomes 1,683,070 visitors annually.

Another top sightseeing recommendation is Roman Forum. This square has been rated 4.7 out of 5 stars in 114,450 reviews.

Colosseum is another attraction you have the opportunity to visit today. This roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 reviews. This popular attraction gets 7,400,000 visits every year.

To continue your sightseeing, head over to Basilica di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars in 27,678 reviews.

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.

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

Vatican City welcomes you with a multitude of unique vacation experiences.

Be one of the day’s first visitors at Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Attracting more than 1,612,530 yearly visitors, it’s a top sight you don’t want to miss.

When you’re finished at Vatican Museums, head to Sistine Chapel. This one-of-a-kind chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 2 hours 39 min, without any stops or traffic disruptions.

Kick off the day at Well of St. Patrick, a top pick for today’s sightseeing. This sightseeing destination is rated an average of 4.5 out of 5 stars in 14,274 reviews.

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

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

Cap off your dinner by heading to Bar Mocambo, ideal for a leisurely evening with a drink in hand. Tree is another bar that offers an enjoyable setting. Similarly, Chupiteria 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 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.

Maximize your last day in Italy and go on a shopping spree in Pisa’s shopping center. This bustling commercial district is conveniently located near your lodging, granting you leisure time to roam and explore its assortment of establishments.

If you love the adrenaline rush of hunting for the best offers and deals in Italy, you’re in for a treat. A variety of goods and gifts await your discovery. Bring a bit of Italy home with you through these charming souvenirs.

Make the most of what's left of your luxury vacation and head out to the stunning Palazzo Gambacorti. This extraordinary palace and attraction is rated an average of 4.3 out of 5 stars in 309 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.

Dine in style at Sud, a top recommendation for dinner tonight. Or, for a change of pace, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Boasts a menu that's sure to impress.

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!