5-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence and surrounding area

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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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Explore the best of Italy on a 5-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Pisa, Florence, Siena, San Gimignano, Monterosso al Mare, Vernazza, and Corniglia. 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 2 nights 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 Piazzale Michelangelo, and immerse yourself in the vibrant atmosphere of Piazza Del Campo.

As you hit the open road and drive through Pisa, Florence, Siena, San Gimignano, Monterosso al Mare, Vernazza, and Corniglia, 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 Gallerypiazzale MichelangeloPonte Vecchio
piazza del CampoSiena CathedralBasilica of San DomenicoFortezza MediceaPorta San GiovanniPiazza del Duomo, San Gimignano
Parrocchia di S. Giovanni BattistaChurch of St. Margaret of AntiochRuins of Doria TowerCinque Terre National Park
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 wonderful meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining spot in Pisa. If you're in the mood for something new, try il Mercante, another premier location with a delectable menu. You might also want to book a table at La Ghiotteria. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

Following your dinner, dive into the local bar culture at Jeffer Cocktails & Friends. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Le Parisien Wine Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Las Volta Cocktailbar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 2

Day 2

  • Pisa
  • Florence
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Drive 94 km, 2 hours 36 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • piazzale Michelangelo
  • Ponte Vecchio
  • More

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Bring your curiosity for today’s adventure around Pisa. Some of the city’s most loved attractions await! Leaning Tower Of Pisa is the perfect place to start. This monument is one of the most iconic places to visit in Pisa. Next, head to Piazza Del Duomo, Pisa, a wondrous public square, known for its stunning 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 Basilica Of Santa Croce In Florence. This culturally significant church is a highly recommended experience. Nearby, you'll also find Uffizi Gallery and Piazzale Michelangelo. Visit these for an interesting touch to your journey. Finish the day with a visit to Ponte Vecchio, a history-steeped historical landmark in Pisa.

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

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

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

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

  • Florence
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Drive 183 km, 3 hours 38 min

  • piazza del Campo
  • Siena Cathedral
  • Basilica of San Domenico
  • Fortezza Medicea
  • Porta San Giovanni
  • Piazza del Duomo, San Gimignano
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On day 3 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and breathtaking views. Start at Piazza Del Campo, a top-rated public square in the city. Then, head to Siena Cathedral and soak in the ambiance of this enchanting church.

There are many interesting places to see in Florence, and when you are ready for more, go to Basilica Of San Domenico. This is one of the city’s most curiosity-inducing stunning spots of interest. After exploring the church, visit the often recommended Fortezza Medicea (siena). Not far away, you'll also find Porta San Giovanni. This monument is a picture-perfect highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazza Del Duomo, a frequently visited public square in the city.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 4

Day 4

  • Florence
  • Pisa
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Drive 304 km, 5 hours 28 min

  • Parrocchia di S. Giovanni Battista
  • Church of St. Margaret of Antioch
  • Ruins of Doria Tower
  • Cinque Terre National Park
  • More

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 3 vibrant destinations - Monterosso al Mare, Vernazza, and Corniglia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Today, you'll explore some of the most beautiful places in Florence, including a church, a monument, and a national park. Start your day with a visit to Parrocchia Di S. Giovanni Battista. This intriguing church is a must-visit in the village. When you’re ready for your next discovery, continue to Church Of St. Margaret Of Antioch, which may be one of the most breathtaking places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Ruins Of Doria Tower, an up-and-coming monument in the village. If you’re up for more discoveries, don’t forget to reserve some time for Cinque Terre National Park.

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.

Indulge in a memorable dining experience at one of Pisa's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a wonderful meal at Ristorante Capodimonte Pisa, a top-rated dining spot in Pisa. If you're in the mood for something new, try La Locanda Dei Pisani Doc Pisa, another premier location with a delectable menu. You might also want to book a table at Baribaldi Pisa. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

Extend your evening after a delightful meal by visiting Bar Mocambo, which offers the perfect atmosphere for a night out. Moreover, Tree is another popular option for a drink or two. Likewise, Chupiteria also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

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Day 5

Day 5

  • Pisa - Departure day
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  • Palazzo Blu
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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 Palazzo Blu. This worthwhile art gallery is a popular place to see in the city.

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 for something new, try Ristorante alle Bandierine, another premier location with a delectable 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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