4-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Siena

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Photo of Aerial view on Rimini. Italian cityscape from above. Lighthouse on water sea canal. Rimini city. Summer vacation.
Photo of Rimini cityscape. Tiberius bridge famous sightseeing in Rimini at dawn. Summer sunrise in Rimini historic center.
Photo of Umbrellas and chaise lounges on the beautiful beach of Rimini in Italy.
Photo of aerial view of umbrellas and chaise lounges on the beautiful beach of Rimini in Italy.
Photo of Bridge on Rimini canal port with boats, modern buildings and old houses.
Photo of Scenic spring view of pier with ancient and modern buildings, ships, yachts and other boats in Rimini, Italy.
Photo of Woman and child outdoors. Mother and daughter going to rest on beach. Rimini, Italy.
Photo of Piazza Tre Martiri Three Martyrs square with traditional buildings with clock and bell tower in old historical touristic city centre Rimini with blue sky background, Emilia-Romagna, Italy
Photo of Umbrellas and chaise lounges on the beautiful beach of Rimini in Italy.
Photo of Blue umbrellas and chaise lounges on the beach of Rimini in Italy.
Photo of Boat in blue water near pier and stone arch Tiberius bridge (Ponte di Tiberio, Augustus Bridge) over Marecchia river in historical city centre Rimini with blue sky white clouds, Emilia-Romagna, Italy.
photo of view of     Bridge of Tiberius, Ponte di Tiberio in Rimini, Italy.
photo oof view of Spectacular morning view of Arch of Augustus. Splendid summer cityscape of Rimini town, Italy, Europe. Traveling concept background.
photo of view of A view down a colourful street in the village area of San Giuliano in Rimini, Italy in summertime
Photo of Siena in Italy by SimonRei
Photo of Siena cathedral against a bright blue sky in Italy.
Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
photo of view of Stylish woman walks on background of cityscape of Siena old town. Concept of travel famous cities in Tosacny region of Italy
photo of view of  Aerial view of Montepulciano, a medieval and Renaissance hill town in the Italian province of Siena in southern Tuscany, Italy
photo of view of Facade decoration of the cathedral of Siena, Italy.
photo of view of historic buildings and landmarks in magnificent medieval Siena,Tuscany, Italy.
photo of view of Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view of Cathedral of the City of Siena in Tuscany region of Italy at sunset.
photo of view of Beautiful traveler girl exploring the historic city of Siena in Tuscany. Young tourist woman smiling at camera in Siena Cathedral square, Tuscany, Italy.
photo of view ofYoung woman having lunch with pizza and wine, sitting with dog at outdoor restaurant with beautiful view on the old town of Siena. Concept of italian cuisine and travel
photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view ofBeautiful view of campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Siena province, Italy
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Escape the ordinary with this exciting 4-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

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 and 1 night in Siena. 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. Piazza Del Campo and Siena Cathedral are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Grande, learn more about the unique Arch Of Augustus, and immerse yourself in the vibrant atmosphere of Piazza Cavour.

As you hit the open road and drive through Rimini, Siena, and Arezzo, 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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Days
Destination
Attractions
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Day
City & Overnight
Attractions
Cavour Square
Malatestiano TempleArco di AugustoParco Federico FelliniLa Ruota PanoramicaSpiaggia libera
piazza del CampoSiena CathedralFortezza Mediceapiazza Grande
Parco XXV Aprile

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Day 1

Day 1

  • Rimini - Arrival day
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  • Cavour Square
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Your road trip adventure in Italy begins as soon as you reach Rimini and pick up your car. You’ll stay in Rimini for 1 night 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.

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 Piazza Cavour, 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.

Don’t miss out on dining at Giusti, a top-rated dining destination in Rimini. If you're in the mood to try something new, consider Bar Lento, another top spot with a mouthwatering menu. You might also want to secure a reservation at Amorimini. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rimini this evening.

Cap off your dinner by heading to Sunflower Beach Backpacker Hostels & Bar, ideal for a leisurely evening with a drink in hand. Caffè Il Borgo is another bar that offers an enjoyable setting. Similarly, Primo Bacio Città Lounge Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise a toast to the start of your 4-day road trip in Italy!

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Day 2

Day 2

  • Rimini
  • Siena
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Drive 233 km, 3 hours 39 min

  • Malatestiano Temple
  • Arco di Augusto
  • Parco Federico Fellini
  • La Ruota Panoramica
  • Spiaggia libera
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Dive into day 2 of your remarkable road trip in Italy. Today you will explore Rimini, 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 Siena. You’ll stay here for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rimini allows for both. Start by heading to Malatestiano Temple. This underrated church provides an insightful glimpse into the city's identity. Next, discover Arch Of Augustus, a heritage-rich monument, promising a delightful encounter.

Continue your sightseeing with a visit to Parco Federico Fellini, a well-known park. When you’re done, don’t forget to make a stop at the up-and-coming La Ruota Panoramica. Round off your day at Spiaggia Libera, another gem in Rimini with romantic features to discover.

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

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

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 3

Day 3

  • Siena
  • Rimini
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Drive 243 km, 4 hours 2 min

  • piazza del Campo
  • Siena Cathedral
  • Fortezza Medicea
  • piazza Grande
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and Arezzo. When you’re not sightseeing, take time to relax at your selected hotel in Rimini, where you’ll be staying for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the impressive Piazza Del Campo, a respected public square in Siena. Next, go to Siena Cathedral.

After visiting Piazza Del Campo and Siena Cathedral, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Fortezza Medicea (siena). This respected monument offers a unique experience. Piazza Grande is another noteworthy attraction worthwhile a visit.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Rimini. 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.

Set out on a gastronomic journey in Rimini by reserving a table at Osteria de Börg. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of from romagna and traditional cuisine. For a different taste, head over to Guido, renowned for its delectable seafood and modern dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Abocar Due Cucine, a highly rated local gem known for its exquisite creative and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rimini.

Unwind after your meal by stepping into Hobo's. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Sunflower City Backpacker offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Capogiro, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

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Day 4

Day 4

  • Rimini - Departure day
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  • Parco XXV Aprile
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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 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 Parco Xxv Aprile, a peaceful park before you head out.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Rimini's best shopping area, Rimini Factory Outlet. 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 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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