Luxury 14-Day Italy Road Trip from Perugia to Rome, Florence, Bologna, and Pisa and surrounding area

Your luxury holiday in Italy begins as soon as you reach the city of Perugia, 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 Piazza IV Novembre. This square is a popular stop on travelers’ itineraries in Perugia, with an average rating of 4.6 out of 5 stars by 9,189 visitors.

Tonight, you will be treated to a stay at one of the best luxury hotels in Perugia. 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 Perugia, 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.

Esteemed as a restaurant, it features an exceptional menu.

If you’re not ready to end the night just yet, Tommi Bar offers a perfect venue to relax and savor a drink. Similarly, Valentina is well-suited for those looking to unwind in a social setting. Caffe Dal Perugino is another excellent spot to enjoy a nightcap after a delightful meal.

Raise a toast to the start of your 14-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 Rome, where you'll be staying for 5 nights. The day's itinerary unfolds with a diverse array of experiences in Perugia.

Rome’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Perugia behind. This drive usually takes around 2 hours 19 min. Rome welcomes you with a multitude of unique vacation experiences.

Journey into the unknown at Carducci Gardens, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.5 out of 5 stars from 1,768 reviews.

When you’re ready to continue your sightseeing, Porta Marzia is a recommended place to visit. This city gate is rated an average of 4.6 out of 5 stars in 119 reviews.

Another must-see attraction in Perugia is Rocca Paolina. Rated an average of 4.7 out of 5 stars by 7,128 travelers, this popular tourist destination in Perugia offers an experience you will remember.

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.

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After your meal, keep the night alive at a bar like La Botticella of Poggi Giovanni, known for its lively atmosphere. Sant' Eustachio Caffè is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the 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.

Day 3 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.

A top pick for your self-guided sightseeing tour today is Villa Borghese. Previous visitors have rated this urban zone of rome an average of 4.6 out of 5 stars in 69,749 reviews.

Piazza del Popolo is a local recommendation that you also can pay a visit today. This square is rated an average of 4.6 out of 5 stars in 89,807 reviews.

Another attraction you won't want to miss is Piazza di Spagna. This square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

Spanish Steps is another outstanding experience in Rome. Around 57,211 travelers have rated this monumental staircase an average of 4.5 out of 5 stars.

If you long for more, Castel Sant'Angelo is not far away. This museum is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.7 out of 5 stars in 72,431 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.

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

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

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.

Piazza Navona is another popular attraction you could visit today. This square has a rating of 4.7 out of 5 stars from 158,771 visitors.

Campo de' Fiori is also highly recommended by travelers. This square has a rating of 4.4 out of 5 stars from 51,133 visitors.

Pantheon is an attraction you won’t want to miss. Around 30,000,000 people visit this place every year. This roman temple is rated an average of 4.8 out of 5 stars in 189,682 reviews.

Another attraction you have the opportunity to visit today is Trevi Fountain. This sculpture has received an average rating of 4.8 out of 5 stars from 343,494 travelers.

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.

Esteemed as a restaurant, it features an exceptional menu.

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 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.

Begin your sightseeing with a visit to Colosseum. This extraordinary roman amphitheatre is rated an average of 4.7 out of 5 stars by 328,821 visitors. Each year, around 7,400,000 people visit this site to learn more about it.

Next, make your way to Roman Forum. This top attraction is a square with an average rating of 4.7 out of 5 stars by 114,450 visitors.

We also recommend a visit to largo di Torre Argentina. This square is rated 4.5 out of 5 stars by 30,433 travelers.

If you’re keen to keep exploring, visit Altare della Patria. This highly recommended sightseeing destination has received an average rating of 4.8 out of 5 stars from 49,843 travelers. Around 1,683,070 people come to experience this place of interest every year.

Today is also your chance to spend some time at Basilica di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars by 27,678 travelers.

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.

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 1 night nights remaining.

Discover a world of culinary delights in Rome, 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.

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 Arezzo. 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 37 min. When you arrive, enjoy some sightseeing.

Start your sightseeing with a visit to San Francesco, Arezzo. This minor basilica is a popular stop on travelers’ itineraries in Arezzo, with an average rating of 4.6 out of 5 stars by 2,377 visitors. Around 20,939 people visit this attraction every year.

Piazza Grande is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 14,465 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Arezzo Cathedral. Visitors have rated this cathedral an average of 4.6 out of 5 stars in 2,450 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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. Esteemed as a 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

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.

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

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.

Start your sightseeing with a visit to piazzale Michelangelo. This square is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 77,744 visitors.

Uffizi Gallery is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 61,794 reviews gives you an idea of other visitors’ experience at this attraction. It’s estimated that around 2,011,219 people visit this national museum every year.

If it’s still bright and early, make your way to Ponte Vecchio. Visitors have rated this deck arch bridge an average of 4.7 out of 5 stars in 118,099 reviews.

Piazza della Signoria is another unique site you can experience today. This attraction is a square rated an average of 4.8 out of 5 stars in 66,956 reviews.

Make your way to the fantastic Basilica of Santa Croce in Florence, perhaps the most famous church in Florence. This attraction is rated 4.7 out of 5 stars by 28,544 travelers.

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

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

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

Continue your road trip and head to your next destination, Bologna. This car ride takes around 1 hour 24 min.

An excellent attraction to start your day with is Cathedral of Santa Maria del Fiore. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Continue your journey at Galleria dell'Accademia. This national museum is rated 4.6 out of 5 stars by 34,429 travelers from near and far. Approximately 1,719,645 people come to this place of interest every year to enjoy a unique experience in Florence.

Florence is also the home of Central Market. This point of interest has an average rating of 4.4 out of 5 stars from 43,100 visitors.

You can continue your self-guided sightseeing tour at Basilica di Santa Maria Novella, Firenze (FI). Rated 4.7 out of 5 stars by 23,075 visitors, a visit to this top sight is time well spent.

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

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

Start your culinary exploration in Bologna by securing a reservation at I Portici. This renowned restaurant holds , and offers an exceptional menu of creative and contemporary cuisine. For another dining delight, visit Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

Following your dinner, dive into the local bar culture at Bar Freud e Squisito. Alternatively, go to Osteria del Sole, the perfect place for those looking to experience the best of the nightlife. Similarly, Macondo - Cocktail Bar provides excellent drinks and a great atmosphere, ensuring 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 10 of your luxury road trip in Italy begins and concludes in the city of Bologna. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Bologna, where you still have 2 nights nights remaining.

An excellent attraction to start your day with is Palazzo Re Enzo. This palazzo is rated an average of 4.6 out of 5 stars in 2,072 reviews.

Continue your journey at Fountain of Neptune, Bologna. This fountain is rated 4.7 out of 5 stars by 3,952 travelers from near and far.

Bologna is also the home of Bologna Cathedral. This catholic cathedral has an average rating of 4.6 out of 5 stars from 3,852 visitors.

You can continue your self-guided sightseeing tour at Piazza Maggiore. Rated 4.7 out of 5 stars by 64,523 visitors, a visit to this top sight is time well spent.

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

After your meal, keep the night alive at a bar like Bar Senza Nome, known for its lively atmosphere. Bar Maurizio is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, BrewDog Bar Bologna offers an excellent atmosphere for those looking to amp up the evening.

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

Day 11 of your luxury road trip in Italy begins and concludes in the city of Bologna. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Bologna, where you still have 1 night nights remaining.

When you're ready to see some sights, Two Towers is a great place to start. This tower is rated an average of 4.7 out of 5 stars by 25,975 visitors.

Another popular attraction you can visit today is International Museum and Library of Music. This music museum has an average rating of 4.5 out of 5 stars from 742 travelers. Every year, 13,413 travelers come to experience this site to make the most of their time in Bologna.

We also recommend a stop at Piazza Santo Stefano. The square has been rated an average of 4.8 out of 5 stars by 7,617 visitors.

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

To truly maximize your evening out, consider visiting Kinotto Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Mio Bar, another bar with an inviting ambiance.

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 12 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 Bologna.

As you’ve unraveled the marvels of Bologna, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 2 hours 7 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready to see some sights, Chiesa del Santissimo Salvatore is a great place to start. This church building is rated an average of 4.6 out of 5 stars by 328 visitors.

Another popular attraction you can visit today is San Martino. This minor basilica has an average rating of 4.6 out of 5 stars from 320 travelers.

We also recommend a stop at La Piccola Venezia. The sightseeing destination has been rated an average of 4.2 out of 5 stars by 1,491 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.

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 another amazing day of your luxury holiday in Bologna, Italy and seize the opportunity to celebrate.

On day 13 of your luxury holiday in Italy, your road trip route will take you exploring the best of Siena and Pisa. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Embrace the thrill of the open road as you wave goodbye to Pisa 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 50 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Begin your sightseeing with a visit to Siena Cathedral. This domus is rated an average of 4.8 out of 5 stars in 21,656 reviews.

Next up, make your way to piazza del Campo. This square has an average rating of 4.8 out of 5 stars from 64,175 reviews.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 50 min. When you arrive in Siena, it's time to take a break from the road.

Start your sightseeing with a visit to Leaning Tower of Pisa. This bell tower is rated an average of 4.7 out of 5 stars from 116,882 visitors. Leaning Tower of Pisa welcomes around 3,200,000 visitors every year.

Piazza del Duomo, Pisa is another popular attraction you could visit today. This square has a rating of 4.7 out of 5 stars from 104,550 visitors.

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

Discover a world of culinary delights in Perugia, 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.

Round off your dining experience by visiting Caffè Fortebraccio, a prime location for a drink. Alternatively, explore the distinctive characteristics of Caffe Del Banco, a bar catering to every mood and preference. Dempsey's Perugia likewise offers a unique atmosphere, perfect for 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.

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 Perugia before saying goodbye.

Make the most of your final day in Italy by visiting Perugia’s iconic markets and shopping establishments. Your stay’s proximity to the city’s retail haven invites an unhurried and unforgettable exploration of its variety of stores and establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. Take home a piece of Italy with these souvenirs, keeping your adventures close.

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

If you're in the mood to try something new, consider Osteria a Priori, another top spot with a mouthwatering menu.

You will then say farewell to Perugia 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!