4-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to Bologna

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Photo of the long staircase in the downtown of the beautiful ancient italian village.
Photo of San Vittore alle Chiuse. Roman Catholic abbey and church. The edifice is known from the year 1011. Ponte Romano. Roman bridge over a small river. Italy. Marche. Ancona.
Photo of Loreto, sacred place in the city of Ancona in the Marche, Italy where the basilica sanctuary of the Holy House is located
Photo of Wonderful view of Arch of Trajan and Cattedrale di San Ciriaco church on background. Sunny summer cityscape of Ancona town, Italy, Europe. Traveling concept background.
Photo of Panorama view of the port of Ancona, Italy.
San Rocco Temple inside the pentagonal 18th century building called Mole Vanvitelliana at dusk. Ancona, Marche Region, Italy.
Photo of Urbani Beach - Sirolo, Ancona, Marche, Italy, Europe.
Photo of Ancona beach, Italy.
Photo of The harbor of Ancona with the rows of the boats docked and city view.
Photo of Panoramic view of old town and port in Ancona.
photo of view of Tourism in Ancona, Italy. Back view of traveler woman enjoying view of Ancona city and seaport from terrace, Marche, Italy.
photo of view of Night view of cathedral of San Ciriaco behind Arco di Traiano in Ancona, Italy.
photo of view of Mole Vanvitelliana also known as the lazaretto of Ancona.
photo of view of  Mole Vanvitelliana also known as the lazaretto of Ancona
Medieval and Renaissance buildings and structures feature in Bologna, Italy
Photo of panoramic view of Bologna,Italy.
Photo of Channel river in Bologna Italy.
Photo of Fontana di Nettuno or Neptune fountain on Piazza Maggiore square at the morning dusk designed by Tommaso Laureti (1565).
Photo of Bologna main square aerial view from Asinelli tower.
Photo of ancient sanctuary of the Madonna di San Luca, old church on the hill.
Photo of quirky castle in the Emilian Apennines, Bologna, Italy.
Photo of Basilica of SantApolinare in Classe.
Photo of View of Basilica di San Petronio on sunrise.
Photo of Sunset view of a small lake located in a park in the center of Bologna, Italy.
Bologna, Italy. View of Basilica di San Petronio on sunrise
Palazzo Re Enzo. Splendid cityscape of Bologna, Italy.
photo of view of Bologna, Italy.
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Experience the freedom of the open road in Italy as you embark on an unforgettable 4-day road trip! This experience caters to every traveler, featuring destinations like Ancona, Senigallia, Bologna, and Rimini.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Ancona and 1 night in Bologna. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Ancona, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Piazza Maggiore and Two Towers are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Frasassi Caves, learn more about the unique Arch Of Augustus, and immerse yourself in the vibrant atmosphere of Piazza Cavour.

As you hit the open road and drive through Ancona, Senigallia, Bologna, and Rimini, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Lazzaretto of Ancona
PassettoCattedrale di San CiriacoFrasassi CavesRocca Roveresca
Piazza MaggioreTwo TowersParco Federico FelliniCavour SquareArco di Augusto
Piazza del Plebiscito

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Day 1

Day 1

  • Ancona - Arrival day
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  • Lazzaretto of Ancona
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Your road trip adventure in Italy begins as soon as you reach Ancona and pick up your car. You’ll stay in Ancona for 1 night and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Ancona is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Lazzaretto Of Ancona, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Ancona. Make yourself at home and enjoy some downtime before heading out again.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Ancona, it's often a good idea to reserve a table in advance.

Dine in style at Playa Solero, a top recommendation for dinner tonight. Or, for a change of pace, Zucchero a Velò boasts a menu that's sure to impress. Also, be sure to check out Ristorante Il Giardino. Known as a local hotspot, it’s a great choice for tonight in Ancona.

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

Raise a toast to the start of your 4-day road trip in Italy!

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Day 2

Day 2

  • Ancona
  • Bologna
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Drive 320 km, 4 hours 6 min

  • Passetto
  • Cattedrale di San Ciriaco
  • Frasassi Caves
  • Rocca Roveresca
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Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 3 vibrant destinations - Ancona, San Vittore, and Senigallia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Ancona is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Passetto, an increasingly popular monument that is worthwhile a visit in the city. Nearby, you’ll find Cathedral Basilica Of St. Cyriacus, enchanting visitors with its historic appeal. Continue your exploration at Frasassi Caves. This cave system is one of the city’s most interesting spots.

Enjoy the freedom of exploring Ancona at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Rocca Roveresca.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you explore more of Bologna, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Start your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-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 Al Bricco D'oro. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Freud E Squisito, the perfect place for those looking to experience the best of the nightlife. Similarly, Osteria Del Sole provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Head back to your accommodation in Bologna and get some rest in preparation for another magical day of your road trip in Italy!

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Day 3

Day 3

  • Bologna
  • Ancona
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Drive 240 km, 3 hours 10 min

  • Piazza Maggiore
  • Two Towers
  • Parco Federico Fellini
  • Cavour Square
  • Arco di Augusto
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Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Bologna and Rimini. At the end of the day, you will enjoy the comforts of a top-rated hotel in Ancona, which will be your home away from home for 1 night.

Savor the day by visiting some of the best places to see in Bologna, including a public square, a monument, and a park. Start your adventure at Piazza Maggiore. This extraordinary public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Two Towers located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Parco Federico Fellini. Its romantic features will captivate you. After the park, continue your tour of the city with a visit to Piazza Cavour. Visitors usually appreciate the visually striking features of this public square. Next up is Arch Of Augustus, a highly recommended monument.

At the end of the day, you will drive to Ancona, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Ancona. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Set out on a gastronomic journey in Ancona by reserving a table at Sot'Ajarchi. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of seafood and from the marches cuisine. Looking for something different? Bontà delle Marche offers a tantalizing alternative with its diverse menu. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Ancona.

After your meal, keep the night alive at a bar like Alla Tazza D'oro, known for its lively atmosphere.

Relax and recharge in preparation for another adventurous day in Italy!

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Day 4

Day 4

  • Ancona - Departure day
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  • Piazza del Plebiscito
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Day 4 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Ancona before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, begin at Piazza Del Plebiscito. This intriguing public square is a popular place to see in the city.

Maximize your last day in Italy and go on a shopping spree in Ancona’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Ancona.

Treat yourself to a delightful dinner at Pizzeria Pulcinella, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Donegal Irish Pub? It's another excellent option with a diverse menu.

You’ll then say farewell to Ancona. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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