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.
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Experience the freedom of the open road in Italy as you embark on an unforgettable 4-day road trip! This experience caters to every traveler, featuring destinations like Perugia, Santa Maria degli Angeli, Spello, Siena, and Florence.

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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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.

As afternoon approaches, head to your chosen hotel in Perugia. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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 top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Tommi Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Valentina offers an ideal atmosphere to enjoy the pleasures of the night. Caffe Dal Perugino is also a great option that provides a perfect setting for a relaxing 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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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.

Savor the day by visiting some of the best places to see in Perugia, including a church, a monument, a palace, a public square and much more! Start your adventure at Basilica Of San Francesco D'assisi. This well-known church is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta Consolare located in Perugia for another exciting encounter.

Next, immerse yourself in the setting of Fortezza Medicea (siena). Its breathtaking features will captivate you. After the monument, continue your tour of the town with a visit to Siena Cathedral. Visitors usually appreciate the history-steeped features of this church. Next up is Pubblico Palace, a highly recommended palace. For a change of pace, head to Piazza Del Campo. As one of the most extraordinary attractions in Perugia, this public square is the perfect place to end your self-guided sightseeing tour.

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.

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

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

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

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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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Dive into day 3 of your remarkable road trip in Italy. Today you will explore Greti and Florence, 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.

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

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

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Perugia. Perugia 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 Perugia's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a delicious meal at La Taverna, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Ristorante del Sole, another top spot with a mouthwatering menu. You might also want to secure a reservation at Al Mangiar Bene. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

Let the evening flow smoothly from dinner to drinks at Caffè Fortebraccio, a top-rated bar in the area. For other recommendations, Caffe Del Banco provides a perfect setting for rounding out your night with style and great drinks. Likewise, Dempsey's Perugia offers a memorable night with diverse drink options and excellent service.

Head back to your accommodation in Perugia and get some rest in preparation for another magical day of your road trip 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, we recommend visiting Rocca Paolina, a photogenic 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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