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
Overnight
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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Your road trip adventure in Italy begins as soon as you reach Perugia and pick up your car. You’ll stay in Perugia 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.

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.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Perugia. Make yourself at home and enjoy some downtime 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 Perugia, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Perugia tonight.

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.

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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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 3 vibrant destinations - Santa Maria degli Angeli, Spello, and Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of fun adventures, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Basilica Of San Francesco D'assisi. This captivating church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Porta Consolare, one of the town’s best highlights.

Next, check out Fortezza Medicea (siena), one of the most up-and-coming places to see in Perugia. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Siena Cathedral. Wander around and soak in the visually striking atmosphere this church offers. Then, head to Pubblico Palace, a top-rated palace that adds another dimension to your day. Finally, visit the impressive Piazza Del Campo, the last of our attraction recommendations for today.

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.

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

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists. Or, head to Maudit Pub. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Impero Siena, another top-rated place in the area.

Raise your glass and celebrate another amazing day 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
  • More

On day 3 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Greti and Florence. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most underrated attractions included on the itinerary is Villa Calcinaia - Conti Capponi. This respected winery will help you start your sightseeing on top. Then, take a leisurely stroll to Piazzale Michelangelo and learn what makes this visually striking observation deck unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the notable Basilica Of Santa Croce In Florence. After exploring the church, head to Uffizi Gallery. This widely recognized art gallery is a highlight in Siena. As your day continues, stop by Ponte Vecchio, known for its visually striking features.

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 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.

Make sure to reserve a table at La Taverna, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante del Sole, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Al Mangiar Bene, a hidden gem nestled in Perugia. 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 Caffè Fortebraccio, known for its lively atmosphere. Caffe Del Banco is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Dempsey's Perugia offers an excellent atmosphere for those looking to amp up the evening.

Celebrate another amazing day of your road trip adventure in Italy!

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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, begin at Rocca Paolina. This worthwhile historical landmark is a popular place to see in the city.

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.

If you're eager to try something different, consider Elfo Pub Perugia, another top spot with a tantalizing menu.

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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