Luxury 14-Day Italy Road Trip from Rome traveling north to Siena, Bologna, Florence, and Perugia

Your luxury holiday in Italy begins as soon as you reach the city of Rome, where you'll be staying for 3 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

When you're ready to see some sights, Altare della Patria is a great place to start. This architectural structure is rated an average of 4.8 out of 5 stars by 49,843 visitors. Altare della Patria attracts more than 1,683,070 visitors every year.

Tonight, you will be treated to a stay at one of the best luxury hotels in Rome. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

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.

Experience a symphony of flavors at La Pergola in Rome by securing a reservation in advance. Renowned for its 3-star Michelin distinction, La Pergola delights its guests with its exceptional variety of meals showcasing delicious mediterranean and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Il Pagliaccio, acclaimed for its delectable creative and innovative specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Enoteca La Torre, a top-rated restaurant known for its outstanding menu. Known as a top-rated , it's a top choice for mediterranean and creative cuisine in the city.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Sant' Eustachio Caffè. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Caffè Portofino, another top-rated place in the area.

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

Day 2 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.

Kick off the day at Castel Sant'Angelo, a top pick for today’s sightseeing. Attracting approximately 918,591 visits every year, this attraction is a must-see. This museum is rated an average of 4.7 out of 5 stars in 72,431 reviews.

Today is also your chance to visit Piazza Navona. Piazza Navona is a square with an average rating of 4.7 out of 5 stars from 158,771 reviews.

Pantheon is another top attraction we highly recommend you visit today. This roman temple is rated an average of 4.8 out of 5 stars by 189,682 visitors. In a single year, this roman temple hosts approximately 30,000,000 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Roman Forum. This square is rated an average of 4.7 out of 5 stars by 114,450 visitors.

Lastly, don’t miss out on Colosseum, a famous roman amphitheatre in Rome. This attraction welcomes 7,400,000 visitors annually and is rated an average of 4.7 out of 5 stars by 328,821 travelers.

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.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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 1 night nights remaining.

Drop by the renowned Villa Borghese. This popular urban zone of rome has been rated an average of 4.6 out of 5 stars by 69,749 visitors.

Another unforgettable place to experience is piazza del Popolo. Rated 4.6 out of 5 stars by 89,807 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Spanish Steps. This monumental staircase has been rated an average of 4.5 out of 5 stars in 57,211 reviews.

Another favorite attraction in the area is Piazza di Spagna. This square and popular place of interest enjoys a rating of 4.7 out of 5 stars from 113,658 local and international travelers.

If you’re keen to explore even more, then consider a visit to Trevi Fountain. With an average rating of 4.8 out of 5 stars from 343,494 travelers, this sculpture is an attraction many avid travelers highly recommend visiting while in Rome.

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.

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

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 holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Vatican City. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Set your GPS to Vatican City and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Vatican City beckons with new experiences!

Journey into the unknown at St. Peter's Basilica, a unique attraction awaiting your visit. This remarkable major basilica has an average rating of 4.8 out of 5 stars from 131,043 reviews. Every year, St. Peter's Basilica welcomes more than 11,000,000 curious visitors.

When you’re ready to continue your sightseeing, Sistine Chapel is a recommended place to visit. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Another must-see attraction in Vatican City is Saint Peter's Square. Rated an average of 4.8 out of 5 stars by 38,954 travelers, this popular tourist destination in Vatican City offers an experience you will remember.

Vatican Museums is another popular stop on travelers' itineraries in Vatican City. This art museum promises memorable moments of exploring. Other travelers have rated this attraction 4.6 out of 5 stars in 133,310 reviews. Each year, approximately 1,612,530 people travel to visit Vatican Museums.

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

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

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

Following your dinner, dive into the local bar culture at Meet Life Cafè. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 Bologna, where you'll be staying for 4 nights. The day's itinerary unfolds with a diverse array of experiences in Siena.

Start your sightseeing with a visit to piazza del Campo. This square is rated an average of 4.8 out of 5 stars from 64,175 visitors.

Basilica of San Domenico is another popular attraction you could visit today. This minor basilica has a rating of 4.6 out of 5 stars from 3,290 visitors.

Siena Cathedral is also highly recommended by travelers. This domus has a rating of 4.8 out of 5 stars from 21,656 visitors.

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

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

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

Dive into a culinary adventure like no other in Bologna by booking a table at I Portici. This popular restaurant holds , and offers an exceptional menu of creative and contemporary cuisine. For another culinary dining option, venture to Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Trattoria di Via Serra, a top local restaurant known for its tantalizing emilian menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

Keep the excitement of the evening going by going to a bar or two. Bar Freud e Squisito is an excellent place to start. You could also check out Osteria del Sole, offering a different kind of charm. A last recommendation for the day is Macondo - Cocktail Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 6 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 3 nights nights remaining.

Seize the day by visiting some of the best attractions in the area, like Two Towers. This extraordinary tower has an average rating of 4.7 out of 5 stars from 25,975 visitors.

Next, make your way to International Museum and Library of Music. This music museum welcomes around 13,413 visitors yearly and is rated an average of 4.5 out of 5 stars in 742 reviews.

While in Bologna, we also recommend a visit to Piazza Santo Stefano. This square has been rated an average of 4.8 out of 5 stars in 7,617 reviews.

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

Esteemed as a restaurant, it features an exceptional menu.

Continue your evening by exploring the vibrant nightlife scene at Bar Senza Nome, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Maurizio, a bar that offers unique local touches. Likewise, BrewDog Bar Bologna provides an excellent alternative for a fun evening.

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

Day 7 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.

Start your sightseeing with a visit to Basilica of San Domenico. This church is a popular stop on travelers’ itineraries in Bologna, with an average rating of 4.7 out of 5 stars by 3,380 visitors.

Porta Castiglione is another popular place of interest you can visit today. The average rating of 4.4 out of 5 stars from 1,086 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Arco del Meloncello. Visitors have rated this arch an average of 4.6 out of 5 stars in 3,755 reviews.

Porta Santo Stefano is another unique site you can experience today. This attraction is a landmark rated an average of 4.3 out of 5 stars in 854 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 Bologna for you, so you can check out the menus and make your reservation in advance.

Keep the evening going at Kinotto Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Mio Bar, which offers a similarly pleasant setting and great drinks.

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 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.

Be one of the day’s first visitors at La Piccola Venezia. This sightseeing destination is rated an average of 4.2 out of 5 stars by 1,491 visitors.

When you’re finished at La Piccola Venezia, head to Ducati Museum. This one-of-a-kind industry museum is rated an average of 4.5 out of 5 stars in 4,028 reviews. Every year, approximately 7,600 travelers come here to experience the industry museum for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Botanical Garden and Herbarium. This museum is rated an average of 4.3 out of 5 stars by 680 visitors.

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

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

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

On day 9 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

A top pick for your self-guided sightseeing tour today is Palazzo d'Accursio. Previous visitors have rated this palazzo an average of 4.6 out of 5 stars in 969 reviews.

Torre dell'Orologio is a local recommendation that you also can pay a visit today. This sightseeing destination is rated an average of 4.7 out of 5 stars in 281 reviews.

Another attraction you won't want to miss is Palazzo Re Enzo. This palazzo is rated an average of 4.6 out of 5 stars in 2,072 reviews.

Piazza Maggiore is another outstanding experience in Bologna. Around 64,523 travelers have rated this square an average of 4.7 out of 5 stars.

If you long for more, Bologna Cathedral is not far away. This catholic cathedral is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.6 out of 5 stars in 3,852 reviews.

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

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience, Santa Elisabetta shines as one of the top destinations known for its delicious creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out SE·STO on Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

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

Day 10 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 2 nights nights remaining.

Start your sightseeing with a visit to Parco delle Cascine. This park is rated an average of 4.3 out of 5 stars from 14,875 visitors.

Pitti Palace is another popular attraction you could visit today. This art museum has a rating of 4.6 out of 5 stars from 23,445 visitors. Pitti Palace attracts up to 198,270 visitors every year.

The Boboli Gardens is also highly recommended by travelers. This park has a rating of 4.2 out of 5 stars from 25,341 visitors.

Central Market is an attraction you won’t want to miss. This point of interest is rated an average of 4.4 out of 5 stars in 43,100 reviews.

Another attraction you have the opportunity to visit today is Basilica di Santa Maria Novella, Firenze (FI). This archives has received an average rating of 4.7 out of 5 stars from 23,075 travelers.

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 Florence. 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.

Day 11 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.

Make Basilica of Santa Croce in Florence your first stop of the day. Previous visitors have rated this church an average of 4.7 out of 5 stars in 28,544 reviews.

Next up, make a stop at Cathedral of Santa Maria del Fiore. With an average rating of 4.8 out of 5 stars by 76,359 visitors, it's easy to understand why so many people visit this church every year.

Galleria dell'Accademia is another attraction you can visit on this day of your vacation. This national museum has an average rating of 4.6 out of 5 stars by 34,429 visitors. Up to 1,719,645 travelers come to Florence every year to see Galleria dell'Accademia with their own eyes.

When you’re finished at Galleria dell'Accademia, the perfect next stop is David. This statue is rated an average of 4.8 out of 5 stars in 10,476 reviews.

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.

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 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.

Seize the day by visiting some of the best attractions in the area, like piazza della Signoria. This extraordinary square has an average rating of 4.8 out of 5 stars from 66,956 visitors.

Next, make your way to Palazzo Vecchio. This palazzo is rated an average of 4.7 out of 5 stars in 19,049 reviews.

While in Florence, we also recommend a visit to Uffizi Gallery. Hosting around 2,011,219 visitors every year, Uffizi Gallery is one of the best places to visit. This national museum has been rated an average of 4.7 out of 5 stars in 61,794 reviews.

If you’re keen to explore even more, then consider a visit to Ponte Vecchio. With an average rating of 4.7 out of 5 stars by 118,099 travelers, this deck arch bridge is a highly recommended stop on your sightseeing around Florence.

Make your way to piazzale Michelangelo, perhaps the most famous square in Florence. This attraction 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 Perugia.

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

After your meal, keep the night alive at a bar like Tommi Bar, known for its lively atmosphere. Valentina is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffe Dal Perugino 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 luxury holiday in Italy has plenty more in store for you.

Wake up to day 13 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 1 night. The day's itinerary unfolds with a diverse array of experiences in Santa Maria degli Angeli.

Santa Maria degli Angeli’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Perugia behind. This drive usually takes around 32 min. Santa Maria degli Angeli welcomes you with a multitude of unique vacation experiences.

Be one of the day’s first visitors at Basilica of San Francesco d'Assisi. This papal basilica is rated an average of 4.9 out of 5 stars by 33,258 visitors.

When you’re finished at Basilica of San Francesco d'Assisi, head to Piazza del Comune. This one-of-a-kind sightseeing destination is rated an average of 4.6 out of 5 stars in 3,057 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Basilica di Santa Chiara. This minor basilica is rated an average of 4.7 out of 5 stars by 9,628 visitors.

Fasten your seatbelt and make your way to your next stop. Santa Maria degli Angeli, 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 Santa Maria degli Angeli to Santa Maria degli Angeli may take around 11 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

A top pick for your self-guided sightseeing tour today is Basilica of Santa Maria degli Angeli. Previous visitors have rated this papal basilica an average of 4.8 out of 5 stars in 19,258 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.

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 stress-free luxury holiday in Italy has plenty more in store for you.

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 Rome before saying goodbye.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Rome’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 Campo de' Fiori. This extraordinary square and attraction is rated an average of 4.4 out of 5 stars in 51,133 reviews, and is an excellent choice for your last sightseeing in Rome.

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

If you're in the mood to try something new, consider Bono Bottega Nostrana - Piazza Di Spagna, another top spot with a mouthwatering menu.

You will then say farewell to Rome 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!