Luxury 5-Day Italy Road Trip from Ancona traveling west to Rimini, and Bologna

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

Be one of the day’s first visitors at Lazzaretto Of Ancona. This building is rated an average of 4.4 out of 5 stars by 4,023 visitors.

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

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

Treat yourself to a delicious dinner at Playa Solero, an excellent option for tonight's dining. Looking for something different? Zucchero a Velò offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Il Giardino. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Ancona.

To truly maximize your evening out, consider visiting Posa Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Four Roses, another bar with an inviting ambiance. Similarly, Amarillo Beer Bar Ancona also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 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 Rimini, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Loreto, Serra San Quirico, San Vittore, and Senigallia.

Fasten your seatbelt and make your way to your next stop. Loreto, 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 Ancona to Loreto may take around 31 min without traffic disruptions. Upon arrival in Loreto, we highly recommend checking out some of the top attractions.

Start your sightseeing with a visit to Sanctuary Of The Holy House Of Loreto. This church is a popular stop on travelers’ itineraries in Loreto, with an average rating of 4.8 out of 5 stars by 19,100 visitors.

Fasten your seatbelt and make your way to your next stop. Serra San Quirico, 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 Loreto to Serra San Quirico may take around 54 min without traffic disruptions. Upon arrival in Serra San Quirico, we highly recommend checking out some of the top attractions.

Begin your sightseeing with a visit to Parco Naturale Regionale Gola Della Rossa E Di Frasassi. This park is rated an average of 4.6 out of 5 stars in 3,515 reviews.

Continue your road trip and head to your next destination, San Vittore. This car ride takes around 13 min.

Take the opportunity to see Frasassi Caves. This attraction has an average rating of 4.8 out of 5 stars from 20,728 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Rimini. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Set out on a gastronomic journey in Rimini by reserving a table at Guido. Renowned for its 1-star Michelin recognition, this restaurant presents an outstanding menu of seafood, and modern cuisine. For a different taste, head over to Abocar Due Cucine, renowned for its delectable creative, and international dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Osteria de Börg, a highly rated local gem known for its exquisite from romagna, and traditional menu. With a Bib Gourmand 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 Rimini.

Let the evening flow smoothly from dinner to drinks at Caffè Il Borgo, a top-rated bar in the area. For other recommendations, Primo Bacio Città Lounge Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Hobo's offers a memorable night with diverse drink options and excellent service.

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

Be one of the day’s first visitors at Arch Of Augustus. This triumphal arch is rated an average of 4.6 out of 5 stars by 12,375 visitors.

When you’re finished at Arch Of Augustus, head to Piazza Cavour. This one-of-a-kind point of interest is rated an average of 4.5 out of 5 stars in 11,447 reviews.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Ravenna. This drive usually takes around 43 min, without any stops or traffic disruptions.

When you’re ready for some sightseeing, make your way to Mirabilandia. This much-appreciated amusement park is rated 4.3 out of 5 stars in 43,418 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Bologna. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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.

Experience a harmony of flavors at I Portici in Bologna by securing a reservation in advance. Known for its 1-star Michelin status, I Portici offers a delightful variety of dishes highlighting its delicious creative, and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Ahimè, a highly recommended restaurant known for its enticing country cooking cuisine. This popular Bib Gourmand-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

Continue your evening by exploring the vibrant nightlife scene at Bar Freud E Squisito, a prime destination for a thrilling night out. Also, don’t forget to check out Osteria Del Sole, a bar that offers unique local touches. Likewise, Macondo - Cocktail Bar provides an excellent alternative for a fun evening.

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

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna, Gradara, and Pesaro. The day's journey will conclude in Ancona, a city that offers you comfort and relaxation for 1 night. 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 Piazza Maggiore. This square is rated an average of 4.7 out of 5 stars in 64,523 reviews.

Next up, make your way to Two Towers. This tower has an average rating of 4.7 out of 5 stars from 25,975 reviews.

When you’re ready for your next sight of the day, continue to Piazza Santo Stefano. This square has an average rating of 4.8 out of 5 stars from 7,617 visitors.

Set your GPS to Gradara and hit the road. Expect a journey of approximately 1 hour 34 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Gradara beckons with new experiences!

Make Gradara Castle one of your first sightseeing stops in Gradara. Rated an average of 4.6 out of 5 stars by 22,114 travelers, a visit to this local attraction makes for a great introduction to the area.

After soaking in Gradara’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pesaro. Expect your car journey to take a minimum of 8 min. When you arrive in Pesaro, it's time to take a break from the road.

Begin your sightseeing with a visit to Parco Naturale Monte San Bartolo. This extraordinary park is rated an average of 4.6 out of 5 stars by 12,733 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Ancona. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Prepare for an extraordinary culinary adventure in Ancona by booking a table at Sot'Ajarchi, a Bib Gourmand restaurant that boasts an exceptional seafood, and from the marches menu. If you're eager to try something different, consider Bontà delle Marche, another top spot with a tantalizing menu.

Continue the enjoyment post-dinner at Alla Tazza D'oro, a cherished local gathering spot renowned for its welcoming atmosphere.

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 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 Ancona before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Ancona’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Make the most of what's left of your luxury vacation and head out to the stunning Passetto. This extraordinary point of interest and attraction is rated an average of 4.5 out of 5 stars in 2,797 reviews, and is an excellent choice for your last sightseeing in Ancona.

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

You will then say farewell to Ancona 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!