4-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena

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Photo of Christmas in Assisi, Saint Francis Basilica with the Christmas Crib. Province of Perugia, Umbria, Italy.
Photo of Aerial view of Perugia from Rocca Paolina, Italy.
Photo of Panoramic view of the Saint Francis Basilica in Assisi, in the Province of Perugia, in the Umbria region of Italy.
photo of view of Sunset panorama view of Italian town Perugia.
photo of view of   Perugia beautiful historical center from Appia Street
photo of view  ofPerugia, Italy town skyline in the morning.
photo  of view  of Perugia, Italy on the medieval Aqueduct Street in the morning.
photo of view of Perugia, Italy. View of Chiesa di San Michele Arcangelo 5th century church known for its circular shape
photo of view of Religious Architecture of The Basilica of Saint Francis of Assisi (Basilica di San Francesco d’Assisi) in Umbria, Perugia Province, Italy. (Part I).
photo of view of  Porta Sole, one of the oldest access point to Perugia, Italy.
photo  of view  ofcourtyard of the convent of San Domenico in Perugia, Italy.
photo  of view of Basilica of San Domenico in Perugia, Umbria, Italy.
photo  of view of Perugia, Italy on the medieval Aqueduct Street in the morning.
photo of view of A glimpse of the ancient Basilica of San Francesco, Assisi, Perugia, Italy
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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Explore the best of Italy on a 4-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Perugia, Santa Maria degli Angeli, Spello, Siena, and Florence. 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 Perugia 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 Perugia, 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. Ponte Vecchio and Piazzale Michelangelo are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Del Campo, learn more about the unique Uffizi Gallery, and immerse yourself in the vibrant atmosphere of Basilica Of San Francesco D'assisi.

As you hit the open road and drive through Perugia, Santa Maria degli Angeli, Spello, Siena, and Florence, 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
Piazza IV Novembre
Basilica of San Francesco d'AssisiPorta ConsolareFortezza MediceaSiena CathedralPubblico Palacepiazza del Campo
Villa Calcinaia - Conti Capponipiazzale MichelangeloBasilica of Santa Croce in FlorenceUffizi GalleryPonte Vecchio
Rocca Paolina

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Day 1

Day 1

  • Perugia - Arrival day
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  • Piazza IV Novembre
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Welcome to Perugia, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night immersing yourself in Perugia's charm before embarking on the next leg of your journey.

Perugia 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 Iv Novembre, 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 Perugia. 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 Perugia, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Ristorante Settimo Sigillo, a highly-rated dining destination in Perugia. If you're eager to try something different, consider Caffè Baglioni, another top spot with a tantalizing menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Perugia this evening.

Continue the enjoyment post-dinner at Tommi Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Valentina offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffe Dal Perugino. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 2

Day 2

  • Perugia
  • Siena
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Drive 181 km, 2 hours 58 min

  • Basilica of San Francesco d'Assisi
  • Porta Consolare
  • Fortezza Medicea
  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
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Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 3 stops and experience some of the highlights of Santa Maria degli Angeli, Spello, and Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Today's adventure in Perugia promises more breathtaking discoveries and enriching experiences! Begin at Basilica Of San Francesco D'assisi. This UNESCO world heritage-designated church is a highlight of any visit in the town. Then, enjoy Porta Consolare, another history-steeped attraction that never fails to captivate visitors. Next, head over to Fortezza Medicea (siena), one of the town’s most increasingly popular attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This history-steeped church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Pubblico Palace, an often recommended palace, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Campo before you head back to your hotel.

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

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

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Day 3

Day 3

  • Siena
  • Perugia
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Drive 253 km, 4 hours 5 min

  • Villa Calcinaia - Conti Capponi
  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
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Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Greti and Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

A blend of fun adventures, romantic experiences, and scenic views await you in Siena on today’s itinerary. First up is the locally appreciated winery, Villa Calcinaia - Conti Capponi. Afterward, continue to Piazzale Michelangelo, an observation deck every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the hamlet. Next, make your way to Basilica Of Santa Croce In Florence. This locally renowned church is an essential stop. Following that, head to Uffizi Gallery, another must-visit site that will enhance your experience. Don’t forget to stop by Ponte Vecchio, a globally renowned historical landmark in the hamlet.

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

As you explore more of Perugia, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Treat yourself to a delightful dinner at La Taverna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante del Sole? It's another excellent option with a diverse menu. Consider reserving a table at Al Mangiar Bene as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

Following your dinner, dive into the local bar culture at Caffè Fortebraccio. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Caffe Del Banco, the perfect place for those looking to experience the best of the nightlife. Similarly, Dempsey's Perugia provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 4

Day 4

  • Perugia - Departure day
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  • Rocca Paolina
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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 Perugia 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 Rocca Paolina, a heritage-rich historical landmark before you head out.

Maximize your last day in Italy and go on a shopping spree in Perugia’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

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

You’ll then say farewell to Perugia. 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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