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

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Explore the best of Italy on a 4-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Senigallia, Bologna, and Rimini. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

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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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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Welcome to Ancona, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night immersing yourself in Ancona's charm before embarking on the next leg of your journey.

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.

Find your way to your hotel in Ancona. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Make sure to reserve a table at Playa Solero, an iconic dining spot in Ancona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Zucchero a Velò, a popular restaurant in Ancona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Il Giardino, a hidden gem nestled in Ancona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Posa Bar, ideal for a leisurely evening with a drink in hand. Bar Four Roses is another bar that offers an enjoyable setting. Similarly, Amarillo Beer Bar Ancona is also a popular place to go on a night out, perfect for relaxing and socializing.

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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On day 2 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Ancona, San Vittore, and Senigallia. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the beloved Passetto, a history-steeped monument in Ancona. Next, go to Cathedral Basilica Of St. Cyriacus.

After visiting Passetto and Cathedral Basilica Of St. Cyriacus, have a stroll along Ancona's streets and take in the local charm. Continue your sightseeing by heading to Frasassi Caves. This instagrammable cave system offers a unique experience. Rocca Roveresca is another noteworthy attraction worthwhile a visit.

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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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.

Cap off your dinner by heading to Bar Al Bricco D'oro, ideal for a leisurely evening with a drink in hand. Bar Freud E Squisito is another bar that offers an enjoyable setting. Similarly, Osteria Del Sole is also a popular place to go on a night out, perfect for relaxing and socializing.

Get a good night's sleep and look forward to another great day on the road 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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Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Bologna and Rimini. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Ancona. You will spend 1 night here for some well-deserved relaxation.

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 impressive 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 enchanting features will captivate you. After the park, continue your tour of the city with a visit to Piazza Cavour. Visitors usually appreciate the enchanting features of this public square. Next up is Arch Of Augustus, a highly recommended monument.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Ancona's most popular restaurants, and connect with friendly locals for an authentic adventure.

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 enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Alla Tazza D'oro, a well-loved spot among locals and tourists.

Savor another day of unforgettable experiences 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 often recommended 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.

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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