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Road trips in Italy

4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence

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Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina

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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 Pisa, Florence, Siena, and San Gimignano. 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 Pisa and 1 night in Florence. 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. Ponte Vecchio and Leaning Tower Of Pisa are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Del Duomo, Pisa, learn more about the unique Cathedral Of Santa Maria Del Fiore, and immerse yourself in the vibrant atmosphere of Piazza Del Campo.

As you hit the open road and drive through Pisa, Florence, Siena, and San Gimignano, 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

Day 1

Knights' Square

Day 2

Leaning Tower of Pisa•Piazza del Duomo, Pisa•Basilica of Santa Croce in Florence•Uffizi Gallery•Ponte Vecchio•Cathedral of Santa Maria del Fiore

Day 3

Fortezza Medicea•piazza del Campo•Siena Cathedral•Porta San Giovanni•Villa Calcinaia - Conti Capponi

Day 4

Palazzo Blu

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Day 1

Pisa - Arrival day
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Knights' Square
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Your road trip adventure in Italy begins as soon as you reach Pisa and pick up your car. You’ll stay in Pisa 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.

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.

As afternoon approaches, head to your chosen hotel in Pisa. 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 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 highly-rated dining destination in Pisa. If you're eager to try something different, consider il Mercante, another top spot with a tantalizing menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Pisa this evening.

After enjoying a fulfilling meal, continue your evening at Jeffer Cocktails & Friends, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Le Parisien Wine Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Las Volta Cocktailbar provides an excellent environment for a relaxed and enjoyable evening.

Raise a toast to the start of your 4-day road trip in Italy!

Day 2

Pisa
Florence
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Drive 91 km, 2 hours 6 min

Leaning Tower of Pisa
Piazza del Duomo, Pisa
Basilica of Santa Croce in Florence
Uffizi Gallery
Ponte Vecchio
Cathedral of Santa Maria del Fiore
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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 Florence. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the timeless Leaning Tower Of Pisa, a historic monument in Pisa. Next, go to Piazza Del Duomo, Pisa.

After visiting Leaning Tower Of Pisa and Piazza Del Duomo, Pisa, have a stroll along Pisa's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of Santa Croce In Florence. This photogenic 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 history-steeped places to visit in Pisa. If you still have some time left for sightseeing, we also recommend stopping by Cathedral Of Santa Maria Del Fiore.

At the end of the day, you will drive to Florence, 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Get a good night's sleep and look forward to another great day on the road in Italy!

Day 3

Florence
Pisa
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Drive 266 km, 4 hours 32 min

Fortezza Medicea
piazza del Campo
Siena Cathedral
Porta San Giovanni
Villa Calcinaia - Conti Capponi
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Siena, San Gimignano, and Greti. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This historic monument is sure to impress. Next on your list is Piazza Del Campo, another must-visit landmark and spectacular public square renowned for its UNESCO world heritage-designated features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Siena Cathedral. This enchanting church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Porta San Giovanni, an underrated monument. Nearby, you'll also find Villa Calcinaia - Conti Capponi, ready to add charm 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 Pisa. Pisa 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 Pisa. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Keep the evening going at Bar Mocambo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Tree, which offers a similarly pleasant setting and great drinks. Another option is Chupiteria, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!

Day 4

Pisa - Departure day
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Palazzo Blu
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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 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 Palazzo Blu, a historic art gallery before you head out.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Pisa's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

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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