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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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Experience the freedom of the open road on an unforgettable 4-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Pisa, Florence, Siena, and San Gimignano.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. 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 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, accommodations, 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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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 here for 1 night and explore what to see in Pisa, 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.

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.

Have a fantastic dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a highly recommended choice for tonight's dinner. If you're looking to mix things up, il Mercante offers an enticing alternative with its varied menu. Additionally, La Ghiotteria is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

Explore the vibrant nightlife at Jeffer Cocktails & Friends after your meal, a hub for lively evenings and memorable moments. Or, head to Le Parisien Wine Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Las Volta Cocktailbar is perfect for those looking to extend their night with a touch of local flavor.

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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Your itinerary for day 2 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 1 night.

Leaning Tower Of Pisa brings Pisa's character to life. This breathtaking monument is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another stunning attraction that never fails to captivate visitors. Next, head over to Basilica Of Santa Croce In Florence, one of the city’s most well-known attractions, known for its photogenic features.

If you’re looking for more, spend time soaking in the atmosphere of Uffizi Gallery. This picture-perfect art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Ponte Vecchio, a wondrous historical landmark, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Cathedral Of Santa Maria Del Fiore before you head back to your hotel.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for a true cultural experience.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

Celebrate another amazing day of your road trip adventure 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, including Siena, San Gimignano, and Greti. When you’re not sightseeing, take time to relax at your chosen hotel in Pisa, where you’ll be staying for 1 night.

Awaiting your discovery is the intriguing Fortezza Medicea (siena), a culturally significant monument in Florence. Next, go to Piazza Del Campo.

After visiting Fortezza Medicea (siena) and Piazza Del Campo, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Siena Cathedral. This majestic church offers a unique experience. Porta San Giovanni is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Villa Calcinaia - Conti Capponi, one of the most romantic places to visit in Florence.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Don’t miss out on dining at Ristorante Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider La Locanda Dei Pisani Doc Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

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.

Head back to your accommodation in Pisa and get some rest to prepare for another magical day of your road trip 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, begin at Palazzo Blu. This locally appreciated art gallery is a hotspot among locals.

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!

How it works

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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

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