Luxury 14-Day Italy Road Trip from Pisa to Florence, Siena, Rome, Arezzo, Padua, and Venice

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!

Make Palazzo Gambacorti one of your first sightseeing stops in Pisa. Rated an average of 4.3 out of 5 stars by 309 travelers, a visit to this local attraction makes for a great introduction to the area.

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.

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.

This -awardee earns consistently high praises from guests. As a top-rated it is an ideal choice in the city.

After savoring a delicious meal, step into the vibrant nightlife at JEFFER cocktails & friends, where the evening is just getting started. In the same way, Le Parisien Wine Bar offers a unique charm perfect for experiencing the local bar scene in Pisa. Las Volta cocktailbar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise a toast to the start of your 14-day luxury vacation in Italy and look forward to more fantastic days to come!

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa and Tirrenia. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Florence’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 1 hour 30 min. Florence welcomes you with a multitude of unique vacation experiences.

A top pick for your self-guided sightseeing tour today is Leaning Tower of Pisa. Over 3,200,000 travelers visit this attraction every year. Previous visitors have rated this bell tower an average of 4.7 out of 5 stars in 116,882 reviews.

Pisa Cathedral is a local recommendation that you also can pay a visit today. This cathedral is rated an average of 4.8 out of 5 stars in 8,361 reviews.

Another attraction you won't want to miss is Piazza del Duomo, Pisa. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.

Campo santo is another outstanding experience in Pisa. Around 586 travelers have rated this cemetery an average of 4.6 out of 5 stars.

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

Take the opportunity to see Bagno degli Americani. This attraction has an average rating of 4.2 out of 5 stars from 2,992 visitors.

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.

Renowned as a restaurant, it offers an exceptional menu. This restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Nestled in the heart of the city, is an ideal choice for discerning foodies seeking culinary excellence.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, SE·STO on Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 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 Ponte Vecchio, a unique attraction awaiting your visit. This remarkable deck arch bridge has an average rating of 4.7 out of 5 stars from 118,099 reviews.

When you’re ready to continue your sightseeing, Uffizi Gallery is a recommended place to visit. This national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. Based on recent data, the attraction hosts 2,011,219 visitors per year.

Another must-see attraction in Florence is piazza della Signoria. Rated an average of 4.8 out of 5 stars by 66,956 travelers, this popular tourist destination in Florence offers an experience you will remember.

Central Market is another popular stop on travelers' itineraries in Florence. This point of interest promises memorable moments of exploring. Other travelers have rated this attraction 4.4 out of 5 stars in 43,100 reviews.

Lastly, don't miss out on Basilica di Santa Maria Novella, Firenze (FI). Rated 4.7 out of 5 stars by 23,075 local and international travelers, it's a popular place to visit.

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 local establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Known as a top-rated , it's a top choice in the city.

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

Wake up to day 4 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.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Siena. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 3 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Start your sightseeing with a visit to Cathedral of Santa Maria del Fiore. This church is rated an average of 4.8 out of 5 stars from 76,359 visitors.

Galleria dell'Accademia is another popular attraction you could visit today. This national museum has a rating of 4.6 out of 5 stars from 34,429 visitors. Galleria dell'Accademia attracts up to 1,719,645 visitors every year.

Basilica of Santa Croce in Florence is also highly recommended by travelers. This church has a rating of 4.7 out of 5 stars from 28,544 visitors.

Piazzale Michelangelo is an attraction you won’t want to miss. This square is rated an average of 4.8 out of 5 stars in 77,744 reviews.

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

Discover a world of culinary delights in Siena, 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.

This renowned restaurant holds , and offers an exceptional menu of cuisine. This acclaimed -recipient consistently leaves guests satisfied, making it a must-visit during your holiday. With a recognition, it guarantees an exceptional dining adventure.

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.

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

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 Rome, where you'll be staying for 3 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

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

Make Sistine Chapel one of your first sightseeing stops in Vatican City. Rated an average of 4.7 out of 5 stars by 52,083 travelers, a visit to this local attraction makes for a great introduction to the area.

St. Peter's Basilica is a worthwhile attraction you can visit next. This major basilica is a valued place of interest in the area, with an average rating of 4.8 out of 5 stars from 131,043 reviews. Up to 11,000,000 travelers visit this site every year to make their time in Vatican City special.

Today is also the perfect opportunity to drop by Saint Peter's Square. This square has been rated an average of 4.8 out of 5 stars by 38,954 visitors.

If you’re keen to explore more, head to Vatican Museums and find out why 1,612,530 people visit this spot every year. A trip to this popular art museum is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 133,310 previous visitors.

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

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

This -awardee earns consistently high praises from guests. As a top-rated it is an ideal choice in the city.

Continue your lively evening at La Botticella of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Sant' Eustachio Caffè is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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 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 to see some sights, Castel Sant'Angelo is a great place to start. This museum is rated an average of 4.7 out of 5 stars by 72,431 visitors. Castel Sant'Angelo attracts more than 918,591 visitors every year.

Another popular attraction you can visit today is Piazza Navona. This square has an average rating of 4.7 out of 5 stars from 158,771 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 di Spagna. This square is a popular attraction with an average rating of 4.7 out of 5 stars from 113,658 reviews.

Piazza del Popolo is another easily accessible place to visit on this day of your trip. Stop by this square, rated 4.6 out of 5 stars in 89,807 reviews, to discover more of what makes it unique.

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.

Renowned as a restaurant, it offers an exceptional menu. This restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Nestled in the heart of the city, is an ideal choice for discerning foodies seeking culinary excellence.

Following your dinner, dive into the local bar culture at The Apartment Bar Roma. Alternatively, go to Hotel Hassler Roma, the perfect place for those looking to experience the best of the nightlife.

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 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.

Make Villa Borghese your first stop of the day. Previous visitors have rated this urban zone of rome an average of 4.6 out of 5 stars in 69,749 reviews.

Next up, make a stop at Basilica di Santa Maria Maggiore. With an average rating of 4.8 out of 5 stars by 27,678 visitors, it's easy to understand why so many people visit this major basilica every year.

Colosseum is another attraction you can visit on this day of your vacation. This roman amphitheatre has an average rating of 4.7 out of 5 stars by 328,821 visitors. Up to 7,400,000 travelers come to Rome every year to see Colosseum with their own eyes.

When you’re finished at Colosseum, the perfect next stop is Roman Forum. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

If you’re keen to explore even more, then consider a visit to Trevi Fountain. This sculpture is a top place to visit, with a rating of 4.8 out of 5 stars from 343,494 reviews.

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

Renowned for its , this restaurant presents an outstanding menu of cuisine. This distinguished -recipient is a favorite among guests, making it a worthy addition to your holiday plans. With an 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 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 8 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

When you’re ready to jump back into the car and say goodbye to Rome, you’ll hit the road in the direction of Arezzo. This drive usually takes around 2 hours 28 min. When you arrive, enjoy some sightseeing.

Seize the day by visiting some of the best attractions in the area, like Altare della Patria. This extraordinary architectural structure has an average rating of 4.8 out of 5 stars from 49,843 visitors. Each year, around 1,683,070 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Pantheon. This roman temple welcomes around 30,000,000 visitors yearly and is rated an average of 4.8 out of 5 stars in 189,682 reviews.

While in Rome, we also recommend a visit to Campo de' Fiori. This square has been rated an average of 4.4 out of 5 stars in 51,133 reviews.

If you’re keen to explore even more, then consider a visit to largo di Torre Argentina. With an average rating of 4.5 out of 5 stars by 30,433 travelers, this square is a highly recommended stop on your sightseeing around Rome.

Make your way to Circus Maximus, perhaps the most famous circus in Rome. This attraction is rated an average of 4.4 out of 5 stars in 44,741 reviews.

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

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

This renowned restaurant holds , and offers an exceptional menu of cuisine. This acclaimed -recipient consistently leaves guests satisfied, making it a must-visit during your holiday. With a recognition, it guarantees an exceptional dining adventure.

Continue the enjoyment post-dinner at Liquid Bar, a cherished local gathering spot renowned for its welcoming atmosphere.

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

Wake up to day 9 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Set your GPS to Bologna and hit the road. Expect a journey of approximately 2 hours 4 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bologna beckons with new experiences!

Be one of the day’s first visitors at Palazzo Re Enzo. This palazzo is rated an average of 4.6 out of 5 stars by 2,072 visitors.

When you’re finished at Palazzo Re Enzo, head to Two Towers. This one-of-a-kind tower is rated an average of 4.7 out of 5 stars in 25,975 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza Santo Stefano. This square is rated an average of 4.8 out of 5 stars by 7,617 visitors.

If you’re keen to explore more, then consider a visit to Piazza Maggiore. This square is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 64,523 visitors.

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

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

Following your dinner, dive into the local bar culture at Il Gottino - Wine Bar. Alternatively, go to Lax, the perfect place for those looking to experience the best of the nightlife. Similarly, BarCode 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.

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 Venice, where you'll be staying for 3 nights. The day's itinerary unfolds with a diverse array of experiences in Padua.

Continue your road trip and head to your next destination, Venice. This car ride takes around 38 min.

Take the opportunity to see Piazza dei Signori, Padua. This attraction has an average rating of 4.7 out of 5 stars from 12,510 visitors.

Piazza della Frutta is another sightseeing hotspot in the area. This square has been rated an average of 4.6 out of 5 stars by 5,397 travelers.

Padua is also the home of Scrovegni Chapel. This chapel gets more than 9,387 visitors on an annual basis. Around 11,849 people have rated this chapel an average of 4.8 out of 5 stars.

Another place you’ll want to visit is The Basilica of St. Anthony. With an average rating of 4.8 out of 5 stars from a total of 38,852 reviews, a visit to this church is a great idea.

This day of your vacation in Padua is also your chance to admire prato della Valle. This must-visit square enjoys an average rating of 4.6 out of 5 stars from 47,576 reviews.

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

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

This -awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. This awardee is a highly recommended choice for an unforgettable meal.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of Adagio, a bar catering to every mood and preference. Il Mercante likewise offers a unique atmosphere, perfect for a memorable night out.

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 11 of your luxury road trip in Italy begins and concludes in the city of Venice. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Venice, where you still have 2 nights nights remaining.

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 Bridge of Sighs. This footbridge is rated an average of 4.6 out of 5 stars in 18,223 reviews.

While in Venice, we also recommend a visit to Doge's Palace. Hosting around 318,104 visitors every year, Doge's Palace is one of the best places to visit. This palace has been rated an average of 4.7 out of 5 stars in 24,775 reviews.

If you’re keen to explore even more, then consider a visit to St Mark's Basilica. With an average rating of 4.7 out of 5 stars by 18,439 travelers, this cathedral is a highly recommended stop on your sightseeing around Venice.

Make your way to Piazza San Marco, perhaps the most famous square in Venice. This attraction is rated an average of 4.7 out of 5 stars in 152,982 reviews.

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 Venice 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. This acclaimed -recipient consistently leaves guests satisfied, making it a must-visit during your holiday. With a recognition, it guarantees an exceptional dining adventure.

Round off your dining experience by visiting The Irish Pub Venezia, a prime location for a drink. Alternatively, explore the distinctive characteristics of Dolce Vita Venezia, a bar catering to every mood and preference. Devils Forest Pub likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 12 of your luxury road trip in Italy begins and concludes in the city of Venice. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Venice, where you still have 1 night nights remaining.

Be one of the day’s first visitors at Venetian Arsenal. This naval arsenal is rated an average of 4.6 out of 5 stars by 8,749 visitors.

When you’re finished at Venetian Arsenal, head to Gallerie dell'Accademia. This one-of-a-kind art museum is rated an average of 4.5 out of 5 stars in 7,950 reviews. Every year, approximately 210,149 travelers come here to experience the art museum for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Peggy Guggenheim Collection. This art museum is rated an average of 4.6 out of 5 stars by 10,128 visitors. Visiting Peggy Guggenheim Collection means you'll be one of 92,922 people who do so every year.

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

This -awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. This awardee is a highly recommended choice for an unforgettable meal.

Extend your evening after a delightful meal by visiting Bar Al Vecio Calice, which offers the perfect atmosphere for a night out.

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 13 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.

Fasten your seatbelt and make your way to your next stop. Pisa, 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 Venice to Pisa may take around 3 hours 37 min without traffic disruptions. Upon arrival in Pisa, we highly recommend checking out some of the top attractions.

Make Palazzo Contarini del Bovolo your first stop of the day. Previous visitors have rated this sightseeing destination an average of 4.5 out of 5 stars in 11,745 reviews.

Next up, make a stop at Teatro La Fenice. With an average rating of 4.7 out of 5 stars by 10,677 visitors, it's easy to understand why so many people visit this opera house every year.

Grand Canal is another attraction you can visit on this day of your vacation. This sightseeing destination has an average rating of 4.8 out of 5 stars by 3,806 visitors.

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.

Renowned for its , this restaurant presents an outstanding menu of cuisine. This distinguished -recipient is a favorite among guests, making it a worthy addition to your holiday plans. With an 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 Pisa.

Keep the evening going at Bar Mocambo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Tree, which offers a similarly pleasant setting and great drinks. Another option is Chupiteria, which provides an inviting environment for unwinding after a busy day out.

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

Today is the last day of your 14-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.

Treat yourself to a final feast. Savor the unique flavors of Pisa one last time before you head to the airport.

This local establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Known as a top-rated , it's a top choice in the city. Treat yourself to a delightful dinner at Sud, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. ? It's another excellent option with a diverse 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!