5-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling south to Siena and Viterbo

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Experience the freedom of the open road in Italy as you embark on an unforgettable 5-day road trip! This experience caters to every traveler, featuring destinations like Pisa, Siena, Orvieto, and Viterbo.

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 Pisa, 1 night in Siena, and 1 night in Viterbo. 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 Pisa, 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. Leaning Tower Of Pisa and Piazza Del Duomo, Pisa 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 Siena Cathedral, and immerse yourself in the vibrant atmosphere of Orvieto Cathedral.

As you hit the open road and drive through Pisa, Siena, Orvieto, and Viterbo, 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
Overnight
Day
City & Overnight
Attractions
Knights' Square
Palazzo BluLeaning Tower of PisaPiazza del Duomo, PisaPisa CathedralParco Regionale Migliarino, San Rossore, Massaciuccoli
piazza del CampoSiena CathedralFortezza MediceaOrvieto CathedralWell of St Patrick
Piazza del PlebiscitoTerme dei papiPalazzo dei Papi di ViterboIl Paese delle Fiabe
“Tuttomondo” (Keith Haring)

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Day 1

Day 1

  • Pisa - Arrival day
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  • Knights' Square
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Say hello to Pisa! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Pisa for 1 night before you continue your adventure!

Pisa 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 Knights' Square, 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 Pisa. 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 Pisa, it's often a good idea to reserve a table in advance.

Don’t miss out on dining at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Unwind after your meal by stepping into Jeffer Cocktails & Friends. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Le Parisien Wine Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Las Volta Cocktailbar, another top-rated bar in the area.

Raise a toast to the start of your 5-day road trip in Italy!

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Day 2

Day 2

  • Pisa
  • Siena
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Drive 133 km, 2 hours 27 min

  • Palazzo Blu
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
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On day 2 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 Pisa and Cascine Vecchie. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Get ready to discover some of the most iconic wonders in Pisa, including an art gallery, a monument, a public square, a church, a nature reserve and much more! Start your day at Palazzo Blu. This standout art gallery is a worthwhile place to see in Pisa. Then, wander over to Leaning Tower Of Pisa. If culturally significant sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Del Duomo, Pisa. This picture-perfect public square is a favorite among visitors.

Pisa offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pisa Cathedral is an increasingly popular spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the mesmerizing Parco Regionale Migliarino, San Rossore, Massaciuccoli. Take a moment to appreciate the fascinating details of this curiosity-inducing nature reserve.

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.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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
  • Viterbo
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Drive 172 km, 3 hours 6 min

  • piazza del Campo
  • Siena Cathedral
  • Fortezza Medicea
  • Orvieto Cathedral
  • Well of St Patrick
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Dive into day 3 of your remarkable road trip in Italy. Today you will explore Siena and Orvieto, 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 Viterbo. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Piazza Del Campo is the perfect place to start. This public square is one of the most impressive places to visit in Siena. Next, head to Siena Cathedral, an interesting church, known for its majestic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Fortezza Medicea (siena). This picture-perfect monument is a highly recommended experience. Nearby, you'll also find Orvieto Cathedral and Well Of St. Patrick. Visit these for an interesting touch to your journey.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Viterbo. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

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Day 4

Day 4

  • Viterbo
  • Pisa
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Drive 304 km, 3 hours 53 min

  • Piazza del Plebiscito
  • Terme dei papi
  • Palazzo dei Papi di Viterbo
  • Il Paese delle Fiabe
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On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Viterbo and Sant'Angelo. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Today’s route brings fun adventures, romantic experiences, and picturesque spots. The first attraction of today is Piazza Del Plebiscito. This underrated public square is a romantic place to see in Viterbo. Continue your discovery at Terme Dei Papi, a romantic spa with stories to tell.

As you stroll around Viterbo, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Palazzo Dei Papi Di Viterbo. This beloved palace offers a standout encounter with Viterbo. Next, make your way to Il Paese Delle Fiabe to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Viterbo.

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

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

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

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

Relax and recharge in preparation for another adventurous day in Italy!

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Day 5

Day 5

  • Pisa - Departure day
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  • “Tuttomondo” (Keith Haring)
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Day 5 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Pisa 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 “tuttomondo” (keith Haring), a detailed art installation before you head out.

On your last day in Italy, take time to indulge in shopping at Pisa’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 Pisa.

If you're in the mood to try something new, consider Ristorante alle Bandierine, another top spot with a mouthwatering menu.

You’ll then say farewell to Pisa. 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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