Luxury 5-Day Italy Road Trip from Trieste traveling south to Bologna

Your luxury holiday in Italy begins as soon as you reach the city of Trieste, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

When you're ready to see some sights, Molo Audace is a great place to start. This landmark is rated an average of 4.7 out of 5 stars by 2,849 visitors.

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.

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

Experience a harmony of flavors at Harry's Piccolo in Trieste by securing a reservation in advance. Known for its 2-star Michelin status, Harry's Piccolo offers a delightful variety of dishes highlighting its delicious creative menu.

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

Raise a toast to the start of your 5-day luxury vacation in Italy and look forward to more fantastic days to come!

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Trieste and Miramare / Miramar. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

A top pick for your self-guided sightseeing tour today is Piazza della Borsa. Previous visitors have rated this square an average of 4.5 out of 5 stars in 4,409 reviews.

Piazza Unità d'Italia is a local recommendation that you also can pay a visit today. This square is rated an average of 4.8 out of 5 stars in 46,036 reviews.

Another attraction you won't want to miss is San Sabba Rice Mill National Monument and Museum. This museum is rated an average of 4.6 out of 5 stars in 5,204 reviews.

Continue your road trip and head to your next destination, Miramare / Miramar.

A top pick for your self-guided sightseeing tour today is Miramare Castle. Over 79,218 travelers visit this attraction every year. Previous visitors have rated this giardino all'italiana an average of 4.7 out of 5 stars in 21,372 reviews.

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

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 Bologna so you can check out the menus and make advance reservations.

Experience a symphony of flavors at I Portici in Bologna by securing a reservation in advance. Renowned for its 1-star Michelin distinction, I Portici delights its guests with its exceptional variety of meals showcasing delicious creative and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Ahimè, acclaimed for its delectable country cooking specialties. This local Bib Gourmand establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Trattoria di Via Serra, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for emilian cuisine in the city.

After your meal, keep the night alive at a bar like Bar Freud e Squisito, known for its lively atmosphere. Osteria del Sole is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Macondo - Cocktail Bar offers an excellent atmosphere for those looking to amp up the evening.

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

On day 3 of your luxurious vacation in Italy, you’ll start and end your day in Bologna, but spend most of the day exploring attractions outside of the city. After a long day of sightseeing, you'll drive back to Bologna, where you'll stay for 1 night more.

Fasten your seatbelt and make your way to your next stop. Senigallia, 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 Bologna to Senigallia may take around 2 hours 2 min without traffic disruptions. Upon arrival in Senigallia, we highly recommend checking out some of the top attractions.

Make Rocca Roveresca your first stop of the day. Previous visitors have rated this sightseeing destination an average of 4.5 out of 5 stars in 5,207 reviews.

Next up, make a stop at Piazza Garibaldi. With an average rating of 4.4 out of 5 stars by 1,563 visitors, it's easy to understand why so many people visit this point of interest every year.

San Germano’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Senigallia behind. This drive usually takes around 36 min. San Germano welcomes you with a multitude of unique vacation experiences.

Seize the day by visiting some of the best attractions in the area, like Grotte nel sottosuolo di Camerano - Biglietteria. This extraordinary sightseeing destination has an average rating of 4.6 out of 5 stars from 1,983 visitors.

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

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

Wake up to day 4 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Trieste, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Bologna and Padua.

Start your sightseeing with a visit to Piazza Maggiore. This square is rated an average of 4.7 out of 5 stars from 64,523 visitors.

Two Towers is another popular attraction you could visit today. This tower has a rating of 4.7 out of 5 stars from 25,975 visitors.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Padua. This drive usually takes around 1 hour 28 min, without any stops or traffic disruptions.

Make prato della Valle your first stop of the day. Previous visitors have rated this square an average of 4.6 out of 5 stars in 47,576 reviews.

Next up, make a stop at The Basilica of St. Anthony. With an average rating of 4.8 out of 5 stars by 38,852 visitors, it's easy to understand why so many people visit this church every year.

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

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

Keep the evening going at coktail bar Trieste | La Preferita, a great choice for enjoying the after-dinner hours with a drink. You could also go to "LIFE" New Bar Torinese Snc, which offers a similarly pleasant setting and great drinks. Another option is White Cafe, which provides an inviting environment for unwinding after a busy day 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 5-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.

Make the most of your final day in Italy by visiting Trieste’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.

Make the most of what's left of your luxury vacation and head out to the stunning Giants' Stairway. This extraordinary point of interest and attraction is rated an average of 4.3 out of 5 stars in 955 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 eager to try something different, consider Sbecolez Trieste, another top spot with a tantalizing 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!