3-Day Italy Self-Drive Road Trip With Itinerary Starting in Ancona

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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
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Explore the best of Italy on a 3-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Urbino, and Gradara. 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. 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. Gradara Castle and Palazzo Ducale are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Cathedral Basilica Of St. Cyriacus, learn more about the unique Piazza Del Plebiscito, and immerse yourself in the vibrant atmosphere of Casa Santi.

As you hit the open road and drive through Ancona, Urbino, and Gradara, 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
Piazza del Plebiscito
Parco della ResistenzaCasa Natale di RaffaelloPalazzo DucaleGradara Castle
Cattedrale di San Ciriaco

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Day 1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
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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 2 nights 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 Piazza Del Plebiscito, 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.

Continue your evening by exploring the vibrant nightlife scene at Posa Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Four Roses, a bar that offers unique local touches. Likewise, Amarillo Beer Bar Ancona provides an excellent alternative for a fun evening.

Raise a toast to the start of your 3-day road trip in Italy!

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Day 2

Day 2

  • Ancona
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Drive 245 km, 3 hours 34 min

  • Parco della Resistenza
  • Casa Natale di Raffaello
  • Palazzo Ducale
  • Gradara Castle
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Greet day 2 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Ancona for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Urbino and Gradara.

Today’s route brings fun adventures, romantic experiences, and natural wonders. The first attraction of today is Parco Della Resistenza. This curiosity-inducing park is a romantic place to see in Ancona. Continue your discovery at Casa Santi, a historic museum with stories to tell.

As you stroll around Ancona, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Palazzo Ducale. This captivating palace offers a standout encounter with Ancona. Next, make your way to Gradara Castle to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Ancona.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Ancona.

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

Savor the flavors at Amarcord, a top pick for dinner tonight. Alternatively, Bontà delle Marche beckons with its unique menu offerings. Also, consider Ristorante Pizzeria Da Romano. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.

Keep the excitement of the evening going by visiting a bar or two. Alla Tazza D'oro is an excellent place to start.

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

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Day 3

Day 3

  • Ancona - Departure day
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  • Cattedrale di San Ciriaco
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Day 3 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 Cathedral Basilica Of St. Cyriacus, a picture-perfect church before you head out.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Ancona's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

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 in the mood to try something new, consider Donegal Irish Pub, another top spot with a mouthwatering 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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