Luxury 9-Day Italy Road Trip from Trieste traveling south to Venice, Florence, Rome, Arezzo, and Bologna

Your luxury holiday in Italy begins as soon as you reach the city of Trieste. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Make Giants' Stairway one of your first sightseeing stops in Trieste. Rated an average of 4.3 out of 5 stars by 955 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 Trieste. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

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

Enjoy an outstanding dining experience at Harry's Piccolo, a 2-star Michelin restaurant offering an exceptional creative menu.

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

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 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 1 night. The day's itinerary unfolds with a diverse array of experiences in Trieste and Miramare / Miramar.

Be one of the day’s first visitors at Piazza della Borsa. This square is rated an average of 4.5 out of 5 stars by 4,409 visitors.

When you’re finished at Piazza della Borsa, head to piazza Unità d'Italia. This one-of-a-kind square is rated an average of 4.8 out of 5 stars in 46,036 reviews.

Upon reaching Miramare / Miramar, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Make Miramare Castle one of your first sightseeing stops in Miramare / Miramar. Rated an average of 4.7 out of 5 stars by 21,372 travelers, a visit to this local attraction makes for a great introduction to the area. This giardino all'italiana attracts 79,218 visitors every year.

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

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

Get ready for an unforgettable culinary journey in Venice by reserving a table at Local. Renowned as a 1-star Michelin restaurant, it offers an exceptional contemporary menu. For a different taste experience, head to Wistèria, recognized for its delicious contemporary and venetian dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Quadri, a local favorite known for its delightful modern cuisine in Venice. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning modern foodies seeking culinary excellence.

Continue the enjoyment post-dinner at Al Parlamento, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Adagio offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Mercante. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 3 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.

Begin your sightseeing with a visit to Rialto Bridge. This stone bridge is rated an average of 4.7 out of 5 stars in 141,666 reviews.

Next up, make your way to Piazza San Marco. This square has an average rating of 4.7 out of 5 stars from 152,982 reviews.

When you’re ready for your next sight of the day, continue to St Mark's Campanile. This bell tower has an average rating of 4.7 out of 5 stars from 3,884 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Doge's Palace. This palace is rated an average of 4.7 out of 5 stars by 24,775 visitors. Visiting Doge's Palace means you'll be one of 318,104 people who do so every year.

If you’re keen to explore even more, then consider a visit to Bridge of Sighs. This footbridge is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 18,223 visitors.

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

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

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

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.

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

On day 4 of your luxury road trip in Italy, you’ll start and end your day in the city of Florence, but jump in the car to visit amazing attractions in the nearby area. After a day of sightseeing, you'll drive back to Florence, where you still have 1 night left.

Be one of the day’s first visitors at Cathedral of Santa Maria del Fiore. This church is rated an average of 4.8 out of 5 stars by 76,359 visitors.

When you’re finished at Cathedral of Santa Maria del Fiore, head to Ponte Vecchio. This one-of-a-kind deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit piazzale Michelangelo. This square is rated an average of 4.8 out of 5 stars by 77,744 visitors.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 1 hour 16 min.

When you're ready to see some sights, Piazza del Duomo, Pisa is a great place to start. This square is rated an average of 4.7 out of 5 stars by 104,550 visitors.

Another popular attraction you can visit today is Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 travelers. Every year, 3,200,000 travelers come to experience this site to make the most of their time in Pisa.

When you’ve completed everything you want to see and do, you will drive back to your luxury accommodation in Florence.

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.

Wake up to day 5 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Tivoli and Vatican City. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Fasten your seatbelt and make your way to your next stop. Tivoli, 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 Florence to Tivoli may take around 3 hours 7 min without traffic disruptions. Upon arrival in Tivoli, we highly recommend checking out some of the top attractions.

An excellent attraction to start your day with is Villa d'Este. This giardino all'italiana typically receives around 139,855 visitors every year and is rated an average of 4.7 out of 5 stars in 25,000 reviews.

Continue your journey at Viale delle Cento Fontane. This sightseeing destination is rated 4.8 out of 5 stars by 638 travelers from near and far.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Vatican City.

Kick off the day at Saint Peter's Square, a top pick for today’s sightseeing. This square is rated an average of 4.8 out of 5 stars in 38,954 reviews.

Today is also your chance to visit St. Peter's Basilica. St. Peter's Basilica is a major basilica with an average rating of 4.8 out of 5 stars from 131,043 reviews. Attracting more than 11,000,000 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

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

After a long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Rome for you, so you can check out the menus and make your reservation in advance.

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its , this restaurant presents an outstanding menu of mediterranean and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean and creative menu. With a 2-star Michelin 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to La Botticella of Poggi Giovanni, known for its inviting atmosphere. Sant' Eustachio Caffè is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

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 6 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 Arezzo, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Rome.

Start your sightseeing with a visit to Roman Forum. This square is rated an average of 4.7 out of 5 stars from 114,450 visitors.

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

Trevi Fountain is also highly recommended by travelers. This sculpture has a rating of 4.8 out of 5 stars from 343,494 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 Piazza Navona. This square has received an average rating of 4.7 out of 5 stars from 158,771 travelers.

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

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

Treat yourself to an extraordinary dining experience at Octavin, a 1-star Michelin restaurant offering an incredible creative menu. As a top-rated it is an ideal choice 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 Liquid Bar, a well-loved spot among locals and tourists.

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.

On day 7 of your luxury holiday in Italy, your road trip route will take you exploring the best of Arezzo and Siena. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Your sightseeing of the day begins at piazza Grande, a remarkable square where it’s easy to get lost in exploration. This top attraction is rated an average of 4.6 out of 5 stars in 14,465 reviews.

As you’ve unraveled the marvels of Arezzo, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Siena may take around 1 hour 10 min. Upon your arrival in Siena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Drop by the renowned piazza del Campo. This popular square has been rated an average of 4.8 out of 5 stars by 64,175 visitors.

Another unforgettable place to experience is Battistero di San Giovanni Battista. Rated 4.6 out of 5 stars by 616 visitors, this church deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Siena Cathedral. This domus has been rated an average of 4.8 out of 5 stars in 21,656 reviews.

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

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.

Experience a taste of local culinary excellence while in Bologna by securing a table at I Portici. Esteemed as a 1-star Michelin restaurant, it features an exceptional creative and contemporary menu. For an alternative taste experience, visit Ahimè, famous for its scrumptious country cooking dishes. This Bib Gourmand venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.

Keep the evening going at Bar Freud e Squisito, a great choice for enjoying the after-dinner hours with a drink. You could also go to Osteria del Sole, which offers a similarly pleasant setting and great drinks. Another option is Macondo - Cocktail Bar, which provides an inviting environment for unwinding after a busy day 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.

Wake up to day 8 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bologna and Padua. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Make Piazza Maggiore one of your first sightseeing stops in Bologna. Rated an average of 4.7 out of 5 stars by 64,523 travelers, a visit to this local attraction makes for a great introduction to the area.

Two Towers is a worthwhile attraction you can visit next. This tower is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 25,975 reviews.

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Padua. Expect your car journey to take a minimum of 1 hour 28 min. When you arrive in Padua, it's time to take a break from the road.

Start your sightseeing with a visit to prato della Valle. This square is rated an average of 4.6 out of 5 stars from 47,576 visitors.

The Basilica of St. Anthony is another popular attraction you could visit today. This church has a rating of 4.8 out of 5 stars from 38,852 visitors.

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

Discover a world of culinary delights in Trieste, 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.

Let the evening flow smoothly from dinner to drinks at coktail bar Trieste | La Preferita, a top-rated bar in the area. For other recommendations, "LIFE" New Bar Torinese Snc provides a perfect setting for rounding out your night with style and great drinks. Likewise, White Cafe offers a memorable night with diverse drink options and excellent service.

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

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 Trieste before saying goodbye.

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

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

Make the most of what's left of your luxury vacation and head out to the stunning Umberto Saba Statue. This extraordinary point of interest and attraction is rated an average of 4.4 out of 5 stars in 270 reviews, and is an excellent choice for your last sightseeing in Trieste.

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

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

You will then say farewell to Trieste 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!