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

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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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Itinerary summary

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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.

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.

Make sure to reserve a table at Ristorante Settimo Sigillo, 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 Caffè Baglioni, 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 Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you’re not ready to end the night just yet, Tommi Bar offers a perfect venue to relax and savor a drink. Similarly, Valentina is well-suited for those looking to unwind in a social setting. Caffe Dal Perugino is another excellent spot to enjoy a nightcap after a delightful meal.

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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Perugia allows for both. Start by heading to Basilica Of San Francesco D'assisi. This captivating church provides an insightful glimpse into the town's identity. Next, discover Porta Consolare, a photogenic monument, promising a delightful encounter.

Continue your sightseeing with a visit to Fortezza Medicea (siena), an underrated monument. When you’re done, don’t forget to make a stop at the well-known Siena Cathedral. Not far away from the church, you will find the history-steeped Piazza Del Campo, perfect for a quick visit. Round off your day at Pubblico Palace, another gem in Perugia with culturally significant features to discover.

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.

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.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Take some time to reflect on your day and savor another beautiful night 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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Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Greti and Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 1 night.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the often recommended Villa Calcinaia - Conti Capponi, a visually striking winery in Siena. Next, go to Piazzale Michelangelo.

After visiting Villa Calcinaia - Conti Capponi and Piazzale Michelangelo, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of Santa Croce In Florence. This culturally significant church offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Ponte Vecchio, one of the most visually striking places to visit in Siena.

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.

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

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Caffè Fortebraccio, known for its inviting atmosphere. Caffe Del Banco is another great option if you’re looking for a place to get the night started. Similarly, Dempsey's Perugia provides a great setting to enjoy the night away.

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

On your last day in Italy, take time to indulge in shopping at Perugia’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

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 in the mood to try something new, consider Elfo Pub Perugia, another top spot with a mouthwatering 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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