5-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling north to Bologna and Padua

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Photo of the long staircase in the downtown of the beautiful ancient italian village.
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Explore the best of Italy on a remarkable 5-day road trip! Combine exploration with relaxation on a self-drive tour featuring Ancona, Serra San Quirico, Senigallia, Bologna, Verona, Padua, and Rimini.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Ancona, 1 night in Bologna, and 1 night in Padua. 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 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. Verona Arena and Piazza Maggiore are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Prato Della Valle, learn more about the unique Two Towers, and immerse yourself in the vibrant atmosphere of Frasassi Caves.

As you hit the open road and drive through Ancona, Serra San Quirico, Senigallia, Bologna, Verona, Padua, 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, accommodations, 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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Pick-up: 10:00
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Day 1

Day 1

  • Ancona - Arrival day
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  • Lazzaretto of Ancona
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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 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.

Keep the evening going at Posa Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Four Roses, which offers a similarly pleasant setting and great drinks. Another option is Amarillo Beer Bar Ancona, which provides an inviting environment for unwinding after a busy day out.

Raise a toast to the start of your 5-day road trip in Italy!

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Day 2

Day 2

  • Ancona
  • Bologna
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Drive 325 km, 4 hours 12 min

  • Parco Naturale Regionale Gola della Rossa e di Frasassi
  • Frasassi Caves
  • Rocca Roveresca
  • Piazza Garibaldi
  • More

Dive into day 2 of your remarkable road trip in Italy. Today you'll explore 3 destinations, including Serra San Quirico, San Vittore, and Senigallia. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna, where you'll spend 1 night.

Your adventure in Ancona is only getting started when you visit Parco Naturale Regionale Gola Della Rossa E Di Frasassi, a curiosity-inducing local hot spot. Another notable attraction to explore is Frasassi Caves. This captivating cave system is known for its picturesque appeal.

After soaking in the highlights of these sights, take some time to wander Ancona's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Rocca Roveresca. This culturally significant castle offers a fascinating experience that many visitors find memorable. Piazza Garibaldi is also worth visiting.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Bologna, it's often a good idea to reserve a table in advance.

Begin 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.

Extend your evening after a delightful meal by visiting Bar Al Bricco D'oro, which offers the perfect atmosphere for a night out. Moreover, Bar Freud E Squisito is another popular option for a drink or two. Likewise, Osteria Del Sole also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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
  • Padua
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Drive 229 km, 3 hours 22 min

  • Two Towers
  • Piazza Maggiore
  • Castelvecchio Museum
  • Castelvecchio Bridge
  • Verona Arena
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Your itinerary for day 3 of your road trip in Italy includes 2 stops and features some of the highlights of Bologna and Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Padua, where you'll spend 1 night.

Two Towers leaves a lasting impression. This monument is one of the most captivating places to visit in Bologna. Next, head to Piazza Maggiore, a spectacular public square, known for its symbolic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Castelvecchio Museum. This historic museum is a highly recommended experience. Nearby, you'll also find Castelvecchio Bridge and Verona Arena. Visit these for an interesting touch to your journey.

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

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

Treat yourself to a wonderful meal at Veganda, a top-rated dining spot in Padua. If you're in the mood for something new, try Osteria Ai Scarponi, another premier location with a delectable menu. You might also want to book a table at Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C). Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Padua.

If you’re not ready to end the night just yet, Il Gottino - Wine Bar offers a perfect venue to relax and savor a drink. Similarly, Brutal is well-suited for those looking to unwind in a social setting. Al Buscaglione is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 4

Day 4

  • Padua
  • Ancona
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Drive 347 km, 4 hours 6 min

  • Piazza dei Signori, Padua
  • Prato della Valle
  • Arco di Augusto
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On day 4 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Padua and Rimini are on today's agenda. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Catch Piazza Dei Signori, Padua before the crowds roll in. This history-steeped public square is sure to ignite your curiosity. Next, dive into the enchanting features of Prato Della Valle, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Arch Of Augustus, a well-known monument.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. Check in and relax 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 a true cultural experience.

Enjoy an outstanding dining experience at Sot'Ajarchi, a Bib Gourmand restaurant offering an exceptional seafood and from the marches menu. Alternatively, experience a taste of Ancona at Bontà delle Marche, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated.

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.

Say good night to Ancona and look forward to another great day of your road trip in Italy!

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Day 5

Day 5

  • Ancona - Departure day
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  • Piazza del Plebiscito
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Day 5 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 locally appreciated public square is a hotspot among locals.

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

If you're eager to try something different, consider Donegal Irish Pub, another top spot with a tantalizing 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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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
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Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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