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

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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 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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Say hello to Pisa! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Pisa for 1 night before you continue your adventure!

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.

Savor the flavors at Anima di Grano Pizzeria Napoletana Pisa Italy, a top pick for dinner tonight. Alternatively, il Mercante beckons with its unique menu offerings. Also, consider La Ghiotteria. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 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 2 nights.

Get ready for an exciting day in Pisa. Today’s sightseeing agenda includes a monument, a public square, a church, an art gallery, an observation deck, a historical landmark and much more! Begin your adventure at Leaning Tower Of Pisa. This is a wondrous monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a globally renowned public square in Pisa.

When you’re ready for the next sight, head to Basilica Of Santa Croce In Florence. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s top-rated attractions. We recommend continuing your self-guided tour at Piazzale Michelangelo, an enchanting place of interest in the city. If time allows, add Ponte Vecchio to your itinerary. This globally renowned historical landmark offers the perfect finishing touch to your day 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.

As you explore more of Florence, 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.

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.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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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
  • More

On day 3 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Siena and San Gimignano. You still have 1 night left in Florence.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the widely recognized Piazza Del Campo, an enchanting public square in Florence. Next, go to Siena Cathedral.

After visiting Piazza Del Campo and Siena Cathedral, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of San Domenico. This grand church offers a unique experience. Fortezza Medicea (siena) is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Porta San Giovanni, one of the most UNESCO world heritage-designated places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Piazza Del Duomo.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

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 Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Say good night to Florence and look forward to another great day of your road trip 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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 3 stops and experience some of the highlights of Monterosso al Mare, Vernazza, and Corniglia. 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.

Today’s agenda in Florence includes a church, a monument, and a national park. Parrocchia Di S. Giovanni Battista is must-visit church and a great starting point for the day. Next, continue your journey to Church Of St. Margaret Of Antioch, a frequently visited church, located just a leisurely stroll away. Next, head to Ruins Of Doria Tower, a history-steeped monument, also available for your discovery today.

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

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.

Continue your evening by exploring the vibrant nightlife scene at Bar Mocambo, a prime destination for a thrilling night out. Also, don’t forget to check out Tree, a bar that offers unique local touches. Likewise, Chupiteria provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences 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, we recommend visiting Palazzo Blu, a standout 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 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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