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

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Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina
Blue hour twilight with Duomo and world famous Leaning Tower travel background in Tuscany.
Landscape with Pisa old town and Arno river, Tuscany, Italy.
 Tourists and locals enjoy a sunny day on the Corso Italia, the main shopping and dining street through the Tuscan city of Pisa, Italy.
Gothic church of Santa Maria della Spina, built around 1230 in the Pisan Gothic style.
Building in botanical garden of Pisa (Orto botanico di Pisa) in Italy
Photo of Tourists at the Primatial Metropolitan Cathedral of the Assumption of Mary in Pisa.
Carriage with horse in front of the leaning tower of Pisa
San Miniato, Pisa, Tuscany, Italy: the ancient catholic theological seminary in the picturesque old town.
Piazza Vittorio Emanuele square in the centre of Pisa city in Tuscany, Italy
Beautiful building of University on Piazza dei Cavalieri (Palazzo della Carovana) decorated with sgraffiti and sculptures of Grand Dukes of Tuscany. The statue depicts Cosimo I de' Medici. Pisa, Italy
The Cittadella Nuova now called the Giardino di Scotto or Giardino Scotto is an old fortress in Pisa, Italy
Piazza dei Cavalieri, Palazzo della Carovana, Palazzo dell'Orologio in Pisa, Italy. Architecture and landmark of Pisa. Cityscape of Pisa
Pisa, Italy. Leaning Tower of Pisa. Panoramic view in the evening. Aerial view
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
View of the valley and town of Civita di Bagnoregio with stone houses on a high cliff in the province of Viterbo, Lazio region, Italy
Scenic lakes of Italy - beautiful Bolsena. aerial view of Capodimonte medieval village. Viterbo province, Lazio region
Viterbo, Italy
Parco dei Mostri,Viterbo, northern Lazio, Italy
Aerial view of the Villa Farnese, a pentagonal mansion in Caprarola, near Viterbo, Italy. It is a massive Renaissance and Mannerist construction. It is built on a five-sided plan in reddish gold stone
The Papal Palace and Cathedral complex in the medieval town of Viterbo, Viterbo northern Lazio, Italy
View at the Catedral of Saint Lawrwnce in the streets of Viterbo in Italy
Orcus mouth sculpture at famous Parco dei Mostri (Park of the Monsters), also named Sacro Bosco (Sacred Grove) or Gardens of Bomarzo in Bomarzo, province of Viterbo, northern Lazio, Italy
San Pellegrino medieval district in Viterbo, Lazio (Italy).
Aerial view of The Villa Farnese (in italian Palazzo Farnese), a mansion in the town of Caprarola, near Viterbo, Northern Lazio, Italy. Birds eye of the ancient village of Caprarola, in Tuscia.
Scenic sight in the natural monument "Forre di Corchiano", near the village of Corchiano, in the Province of Viterbo, Lazio, Italy.
Tuscania, Viterbo, Lazio. A glimpse of the ancient medieval village of Tuscania, city of the Etruscans. The ancient Romanesque church of San Pietro with the large central arch and rose window.
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Escape the ordinary with this exciting 5-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

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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Welcome to Pisa, 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 Pisa's charm before embarking on the next leg of your journey.

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.

Find your way to your hotel in Pisa. 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 Pisa, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal 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.

Continue the enjoyment post-dinner at Jeffer Cocktails & Friends, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Le Parisien Wine Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Las Volta Cocktailbar. 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 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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Dive into day 2 of your remarkable road trip in Italy. Today you will explore Pisa and Cascine Vecchie, 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 Siena. You’ll stay here for 1 night.

Get ready for a day filled with family-friendly attractions, picturesque spots, and historic treasures in the charming city of Pisa. Your adventure starts at Palazzo Blu, an up-and-coming local hot spot. Another notable attraction to explore is Leaning Tower Of Pisa. This world-famous monument is known for its photogenic appeal.

After soaking in the highlights of these sights, take some time to wander Pisa's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Del Duomo, Pisa. This breathtaking public square offers a fascinating experience that many visitors find memorable. Pisa Cathedral is also worth visiting, along with Parco Regionale Migliarino, San Rossore, Massaciuccoli. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

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.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

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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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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 Siena and Orvieto. In the evening, you’ll end up in Viterbo, where you will stay for 1 night.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Piazza Del Campo. This top-rated public square is an enchanting place to see in Siena. Continue your discovery at Siena Cathedral, a majestic church with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Fortezza Medicea (siena). This intriguing monument offers a breathtaking encounter with Siena. Next, make your way to Orvieto Cathedral to add another highlight to your day. After that, visit Well Of St. Patrick, a captivating monument that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

At the end of the day, you will drive to Viterbo, 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 Viterbo's most popular restaurants, and connect with friendly locals for an authentic adventure.

Take some time to reflect on your day and savor another beautiful night 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
  • More

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Viterbo and Sant'Angelo. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Set out on a day brimming with fun adventures, romantic experiences, and photo-friendly spots. Start at the underrated Piazza Del Plebiscito, a romantic public square in Viterbo. Next, go to Terme Dei Papi.

After visiting Piazza Del Plebiscito and Terme Dei Papi, have a stroll along Viterbo's streets and take in the local charm. Continue your sightseeing by heading to Palazzo Dei Papi Di Viterbo. This breathtaking palace offers a unique experience. Il Paese Delle Fiabe is another noteworthy attraction worthwhile a visit.

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.

As you explore more of Pisa, 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.

Enjoy a lovely dining experience at Ristorante Capodimonte Pisa, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at La Locanda Dei Pisani Doc Pisa, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Baribaldi Pisa. It’s yet another ideal choice to enhance your time in Pisa tonight.

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

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, begin at “tuttomondo” (keith Haring). This worthwhile art installation is a popular place to see in the city.

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.

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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