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

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Escape the ordinary with this exciting 4-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

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.

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.

Treat yourself to a wonderful meal at Playa Solero, a top-rated dining spot in Ancona. If you're in the mood for something new, try Zucchero a Velò, another premier location with a delectable menu. You might also want to book a table at Ristorante Il Giardino. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.

Let the evening flow smoothly from dinner to drinks at Posa Bar, a top-rated bar in the area. For other recommendations, Bar Four Roses provides a perfect setting for rounding out your night with style and great drinks. Likewise, Amarillo Beer Bar Ancona offers a memorable night with diverse drink options and excellent service.

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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Dive into day 2 of your remarkable road trip in Italy. Today you will explore Ancona, San Vittore, and Senigallia, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna. You’ll stay here for 1 night.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Ancona. Begin your sightseeing with Passetto. This increasingly popular monument is one of the top attractions in the city. Proceed to Cathedral Basilica Of St. Cyriacus, another must-visit attraction.

As you wander through the inviting streets of Ancona, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Frasassi Caves. This popular cave system is a traveler-favorite. Not far away, you’ll find Rocca Roveresca, another key site on your sightseeing itinerary.

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.

After a day of adventure, treat yourself to an exquisite dinner at one of Bologna's best restaurants.

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

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.

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.

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most impressive attractions included on the itinerary is Piazza Maggiore. This visually striking public square will help you start your sightseeing on top. Then, take a leisurely stroll to Two Towers and learn what makes this culturally significant monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the interesting Parco Federico Fellini. After exploring the park, head to Piazza Cavour. This notable public square is a highlight in Bologna. As your day continues, stop by Arch Of Augustus, known for its eye-catching features.

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.

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

Get ready for an unforgettable culinary journey in Ancona by reserving a table at Sot'Ajarchi. Renowned as a Bib Gourmand restaurant, it offers an exceptional seafood and from the marches menu. If you're in the mood to try something new, consider Bontà delle Marche, another top spot with a mouthwatering menu.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Alla Tazza D'oro stands out as an excellent choice for a post-dinner cocktail.

Raise your glass and celebrate another amazing day of your road trip 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, we recommend visiting Piazza Del Plebiscito, a romantic public square before you head out.

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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