4-Day Italy Road Trip from Ancona to Bologna

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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, Serra San Quirico, 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.

As you hit the open road and drive through Ancona, Serra San Quirico, 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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Day 1

Day 1 – Ancona - arrival day

  • Ancona - Arrival day
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  • Mole Vanvitelliana
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Say hello to Ancona! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Ancona for 1 night before you continue your adventure!

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 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 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.

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.

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, Serra San Quirico, San Vittore, Senigallia, and Bologna

  • Bologna
  • Serra San Quirico
  • Senigallia
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Drive 323 km, 4 hours 1 min

  • Parco Naturale Regionale Gola della Rossa e di Frasassi
  • Frasassi Caves
  • Rocca Roveresca
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Dive into day 2 of your remarkable road trip in Italy. Today you will explore Serra San Quirico, 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.

Embrace the thrill of the open road as you wave goodbye to Ancona and set your GPS to Serra San Quirico. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 51 min. Upon reaching Serra San Quirico, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready to see some sights, Parco Naturale Regionale Gola Della Rossa E Di Frasassi is a great place to start. This park is rated an average of 4.6 out of 5 stars by 3,515 visitors.

When you’ve had your share of Serra San Quirico, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of San Vittore. Your travel time is around 13 min.

When you’re ready for some sightseeing, make your way to Frasassi Caves. This much-appreciated show cave is rated 4.8 out of 5 stars in 20,728 reviews.

When you’re done exploring for the day, you’ll drive to Bologna, where you'll have a hotel waiting for you. Check in and spend some time relaxing before you head out to explore the city.

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

Discover the culinary delights of Bologna by securing a reservation at Ahimè. Esteemed for its a Bib Gourmand award, this restaurant offers a remarkable selection of country cooking cuisine. For an alternative dining experience, try I Portici, renowned for its delicious creative, and contemporary dishes. This esteemed 1-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Trattoria di Via Serra, a highly recommended local eatery celebrated for its mouthwatering emilian menu. With its Bib Gourmand recognition, it offers an unforgettable dining adventure.

Unwind after your meal by stepping into Bar Freud E Squisito. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Osteria Del Sole offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Macondo - Cocktail Bar, another top-rated bar in the area.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 3

Day 3 – Bologna, Rimini, and Ancona

  • Ancona
  • Bologna
  • Rimini
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Drive 237 km, 3 hours 4 min

  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • Arco di Augusto
  • Cavour Square
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Bologna, and Rimini. When you’re not sightseeing, take time to relax at your selected hotel in Ancona, where you’ll be staying for 1 night.

When you’re ready for some sightseeing, make your way to Piazza Maggiore. This much-appreciated square is rated 4.7 out of 5 stars in 64,523 reviews.

Next up is Two Towers. This tower has an average rating of 4.7 out of 5 stars from 25,975 visitors.

Another top sightseeing recommendation is Piazza Santo Stefano. This square has been rated 4.8 out of 5 stars in 7,617 reviews.

As you’ve unraveled the marvels of Bologna, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Rimini may take around 1 hour 24 min. Upon your arrival in Rimini, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Journey into the unknown at Arch Of Augustus, a unique attraction awaiting your visit. This remarkable triumphal arch has an average rating of 4.6 out of 5 stars from 12,375 reviews.

When you’re ready to continue your sightseeing, Piazza Cavour is a recommended place to visit. This point of interest is rated an average of 4.5 out of 5 stars in 11,447 reviews.

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.

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

Treat yourself to an extraordinary dining experience at Sot'Ajarchi, a Bib Gourmand restaurant offering an incredible seafood, and from the marches menu. Alternatively, if your taste buds call for something different, Bontà delle Marche is another top choice with a popular menu.

Keep the evening going at Alla Tazza D'oro, a great choice for enjoying the after-dinner hours with a drink.

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

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Day 4

Day 4 – Ancona - departure day

  • Ancona - Departure day
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  • Passetto
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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.

Make the most of your final day in Italy by visiting Ancona’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

Be one of the day’s first visitors at Passetto. This sightseeing destination is rated an average of 4.5 out of 5 stars by 2,797 visitors.

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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