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

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Photo of Bright summer view from flying drone of Cattedrale di San Ciriaco church and San Gregorio Illuminatore - Catholic church. Stunning morning cityscape of Ancona town, Italy, Europe.

Photo of the long staircase in the downtown of the beautiful ancient italian village.

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

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Escape the ordinary with this exciting 3-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

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. 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. Gradara Castle and Palazzo Ducale are just a couple of the bucket-list attractions that await your discovery.

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, 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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Day1

Day 1

Ancona - Arrival day
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Piazza del Plebiscito
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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 2 nights discovering what to see in Ancona 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 Piazza Del Plebiscito. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Ancona. Make yourself at home and unwind before heading 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 Ancona, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Playa Solero, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Zucchero a Velò? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Il Giardino as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Ancona.

After savoring a delicious meal, step into the vibrant nightlife at Posa Bar, where the evening is just getting started. In the same way, Bar Four Roses offers a unique charm perfect for experiencing the local bar scene in Ancona. Amarillo Beer Bar Ancona is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day2

Day 2

Ancona
Urbino
Gradara
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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 have 1 night to stay in Ancona, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Urbino and Gradara.

As you explore Urbino’s charming streets, take in the lively atmosphere and get to know the character of the town.

Embrace the thrill of the open road as you wave goodbye to Ancona and set your GPS to Urbino. 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 1 hour 23 min. Upon reaching Urbino, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Parco Della Resistenza, a locally appreciated park that everyone visiting Urbino should see. Next, head to Casa Santi. This historic museum is one of the most often recommended attractions in the region.

If you're keen to see more, don’t miss out on Palazzo Ducale, an UNESCO world heritage-designated palace popular among locals as well as travelers.

Embrace the thrill of the open road as you wave goodbye to Urbino and set your GPS to Gradara. 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 47 min. Upon reaching Gradara, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

One of our top recommendations for your sightseeing is Gradara Castle. Spend some time admiring the enchanting features of the castle before you continue to your next stop.

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

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

Treat yourself to a delightful dinner at Amarcord, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bontà delle Marche? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Pizzeria Da Romano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Ancona.

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

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Day3

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, begin at Cathedral Basilica Of St. Cyriacus. This intriguing church 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.

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!

How it works

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Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

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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.

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.

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.

We guarantee

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

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