5-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling east to Ancona and Perugia

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Photo of Aerial view on Rimini. Italian cityscape from above. Lighthouse on water sea canal. Rimini city. Summer vacation.
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Experience the freedom of the open road in Italy as you embark on an unforgettable 5-day road trip! This experience caters to every traveler, featuring destinations like Rimini, Viserbella, Ancona, Loreto, Senigallia, Perugia, Santa Maria degli Angeli, Pesaro, and Gradara.

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 Rimini, 1 night in Ancona, and 1 night in Perugia. 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 Rimini, 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. Basilica Of San Francesco D'assisi and Gradara Castle are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Frasassi Caves, learn more about the unique Basilica Of Santa Maria Degli Angeli, and immerse yourself in the vibrant atmosphere of Sanctuary Of The Holy House Of Loreto.

As you hit the open road and drive through Rimini, Viserbella, Ancona, Loreto, Senigallia, Perugia, Santa Maria degli Angeli, Pesaro, 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
Arco di Augusto
Parco Federico FelliniSpiaggia liberaItalia in miniatura
PassettoLazzaretto of AnconaSanctuary of the Holy House of LoretoRocca RoverescaFrasassi Caves
Basilica of Santa Maria degli AngeliBasilica of San Francesco d'AssisiParco Naturale Monte San BartoloGradara Castle
Cavour Square

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Day 1

Day 1

  • Rimini - Arrival day
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  • Arco di Augusto
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Say hello to Rimini! 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 Rimini for 1 night before you continue your adventure!

Rimini 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 Arch Of Augustus, 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 Rimini. 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 Rimini, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Giusti, an iconic dining spot in Rimini. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bar Lento, a popular restaurant in Rimini. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Amorimini, a hidden gem nestled in Rimini. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your meal, keep the night alive at a bar like Sunflower Beach Backpacker Hostels & Bar, known for its lively atmosphere. Caffè Il Borgo is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Primo Bacio Città Lounge Bar offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 2

Day 2

  • Rimini
  • Ancona
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Drive 133 km, 1 hour 52 min

  • Parco Federico Fellini
  • Spiaggia libera
  • Italia in miniatura
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Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Rimini and Viserbella. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Ancona. You will spend 1 night here for some well-deserved relaxation.

Rimini is brimming with adventures. Today’s wonderful stops include a park, a beach, and an amusement park. Begin your sightseeing adventure at the captivating Parco Federico Fellini and allow yourself time to explore. Just a short distance away you'll find your next stop, Spiaggia Libera, a mesmerizing beach that draws visitors from far and near.

Continue your journey to Italia In Miniatura, one of the city’s most interesting spots that you shouldn’t miss.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Ancona. Ancona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Set out on a gastronomic journey in Ancona by reserving a table at Sot'Ajarchi. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of seafood and from the marches cuisine. Looking for something different? Zucchero a Velò offers a tantalizing alternative with its diverse menu. With its reputation for pleasing customers, it’s a fantastic choice for tonight 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.

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

  • Ancona
  • Perugia
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Drive 238 km, 3 hours 27 min

  • Passetto
  • Lazzaretto of Ancona
  • Sanctuary of the Holy House of Loreto
  • Rocca Roveresca
  • Frasassi Caves
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Dive into day 3 of your remarkable road trip in Italy. Today you will explore Ancona, Loreto, Senigallia, and San Vittore, 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 Perugia. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Ancona, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Passetto, a curiosity-inducing monument in the city. Then, head to Lazzaretto Of Ancona and soak in the ambiance of this respected museum.

There are many interesting places to see in Ancona, and when you are ready for more, go to Sanctuary Of The Holy House Of Loreto. This is one of the city’s most notable stunning spots of interest. After exploring the church, visit the locally appreciated Rocca Roveresca. Not far away, you'll also find Frasassi Caves. This cave system is a scenic highlight in Ancona.

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

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

Have a fantastic dining experience at Ristorante Settimo Sigillo, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffè Baglioni offers an enticing alternative with its varied menu. Additionally, Bar Pellas is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Perugia.

After your meal, keep the night alive at a bar like Tommi Bar, known for its lively atmosphere. Valentina is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffe Dal Perugino offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!

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Day 4

Day 4

  • Perugia
  • Rimini
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Drive 218 km, 3 hours 33 min

  • Basilica of Santa Maria degli Angeli
  • Basilica of San Francesco d'Assisi
  • Parco Naturale Monte San Bartolo
  • Gradara Castle
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On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Santa Maria degli Angeli, Pesaro, and Gradara. When you’re not sightseeing, take time to relax at your selected hotel in Rimini, where you’ll be staying for 1 night.

Perugia is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and picturesque spots! Start at Basilica Of Santa Maria Degli Angeli, a popular church that is worthwhile a visit in the village. Nearby, you’ll find Basilica Of San Francesco D'assisi, enchanting visitors with its UNESCO world heritage-designated appeal. Continue your exploration at Parco Naturale Monte San Bartolo. This nature reserve is one of the village’s most popular spots.

Enjoy the freedom of exploring Perugia at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Gradara Castle.

When you’re done exploring for the day, you’ll drive to your hotel in Rimini. Check in and spend some time relaxing before you head out to tour the city.

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

Enjoy an outstanding dining experience at Osteria de Börg, a Bib Gourmand restaurant offering an exceptional from romagna and traditional menu. Alternatively, if you're in the mood for something different, consider the nearby 1-star Michelin-awardee, Guido, known for its delicious seafood and modern cuisine. Another highly-recommended place to eat in Rimini is Abocar Due Cucine, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious creative and international menu.

Keep the excitement of the evening going by visiting a bar or two. Hobo's is an excellent place to start. You could also check out Sunflower City Backpacker, offering a different kind of charm. A last recommendation for the day is Bar Capogiro. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 5

Day 5

  • Rimini - Departure day
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  • Cavour Square
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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 Rimini 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 Cavour, a visually striking public square before you head out.

Make the most of your final day in Italy by visiting Rimini’s iconic markets and shopping establishments in the buzzing Rimini Centro. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. You can also browse through boutiques for stylish fashion choices.

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

You’ll then say farewell to Rimini. 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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