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
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
Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
photo of view of Florence,Italy.
photo of view of Florence,Italy.
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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 Pisa, Florence, Siena, and San Gimignano.

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
Overnight
Day
City & Overnight
Attractions
Knights' Square
Leaning Tower of PisaPiazza del Duomo, PisaBasilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioCathedral of Santa Maria del Fiore
Fortezza Mediceapiazza del CampoSiena CathedralPorta San GiovanniVilla Calcinaia - Conti Capponi
Palazzo Blu

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Day 1

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.

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.

Treat yourself to a delightful dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try il Mercante? It's another excellent option with a diverse menu. Consider reserving a table at La Ghiotteria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

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!

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Day 2

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
  • More

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Pisa and Florence, 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 Florence. You’ll stay here for 1 night.

Pisa is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Leaning Tower Of Pisa, a globally renowned monument that is worthwhile a visit in the city. Nearby, you’ll find Piazza Del Duomo, Pisa, enchanting visitors with its culturally significant appeal. Continue your exploration at Basilica Of Santa Croce In Florence. This church is one of the city’s most interesting spots.

Enjoy the freedom of exploring Pisa at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Uffizi Gallery. After exploring the art gallery, head to the iconic Ponte Vecchio. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Cathedral Of Santa Maria Del Fiore, a place of history-steeped interest in Pisa.

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.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 3

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
  • More

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, San Gimignano, and Greti. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

A blend of family-friendly attractions, scenic views, and photo-friendly spots await you in Florence on today’s itinerary. First up is the often recommended monument, Fortezza Medicea (siena). Afterward, continue to Piazza Del Campo, a public square every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Siena Cathedral. This popular church is an essential stop. Following that, head to Porta San Giovanni, another must-visit site that will enhance your experience. Don’t forget to stop by Villa Calcinaia - Conti Capponi, an underrated winery in the city.

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.

Dine in style at Ristorante Capodimonte Pisa, a top recommendation for dinner tonight. Or, for a change of pace, La Locanda Dei Pisani Doc Pisa boasts a menu that's sure to impress. Also, be sure to check out Baribaldi Pisa. Known as a local hotspot, it’s a great choice for tonight in Pisa.

To truly maximize your evening out, consider visiting Bar Mocambo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Tree, another bar with an inviting ambiance. Similarly, Chupiteria also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 4

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 history-steeped 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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