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

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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, and Lucca. 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, 1 night in Florence, and 1 night in Siena. 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 Cathedral Of Santa Maria Del Fiore.

As you hit the open road and drive through Pisa, Florence, Siena, San Gimignano, and Lucca, 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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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 Vecchiopiazza della Signoria
Cathedral of Santa Maria del FioreDavidpiazzale MichelangeloSiena Cathedralpiazza del Campo
Chiesa di Sant'AgostinoPiazza dell'AnfiteatroGuinigi TowerSt Martin CathedralPiazza NapoleoneWalls of Lucca
“Tuttomondo” (Keith Haring)

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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.

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.

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Jeffer Cocktails & Friends, a great choice for enjoying the after-dinner hours with a drink. You could also go to Le Parisien Wine Bar, which offers a similarly pleasant setting and great drinks. Another option is Las Volta Cocktailbar, which provides an inviting environment for unwinding after a busy day 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
  • More

Drive 91 km, 1 hour 57 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • piazza della Signoria
  • More

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Get ready for an exciting day in Pisa. Today’s sightseeing agenda includes a monument, a public square, a church, an art gallery, 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 timeless 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 famous attractions. We recommend continuing your self-guided tour at Ponte Vecchio, a visually striking place of interest in the city. If time allows, add Piazza Della Signoria to your itinerary. This famous public square offers the perfect finishing touch to your day 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 day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 3

Day 3

  • Florence
  • Siena
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Drive 78 km, 1 hour 36 min

  • Cathedral of Santa Maria del Fiore
  • David
  • piazzale Michelangelo
  • Siena Cathedral
  • piazza del Campo
  • 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 Florence and Siena. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Cathedral Of Santa Maria Del Fiore. This history-steeped church is a highlight of any visit in the city. Next, head over to Piazzale Michelangelo, one of the city’s most top-rated attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This symbolic church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Campo, a widely recognized public square, and take a stroll around the area.

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

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!

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Day 4

Day 4

  • Siena
  • Pisa
  • More

Drive 152 km, 3 hours 15 min

  • Chiesa di Sant'Agostino
  • Piazza dell'Anfiteatro
  • Guinigi Tower
  • St Martin Cathedral
  • Piazza Napoleone
  • Walls of Lucca
  • More

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, San Gimignano and Lucca. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Bring your curiosity for today’s adventure around Siena. Some of the village’s most loved attractions await! Chiesa Di Sant'agostino is the perfect place to start. This church is one of the most curiosity-inducing places to visit in Siena. Next, head to Piazza Dell'anfiteatro, an interesting public square, known for its awe-inspiring 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 Guinigi Tower. This majestic monument is a highly recommended experience. Nearby, you'll also find St Martin Cathedral and Piazza Napoleone. Visit these for an interesting touch to your journey. Finish the day with a visit to Mura Di Lucca, a respected historical landmark in Siena.

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 you explore more of Pisa, 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 Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Locanda Dei Pisani Doc Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Baribaldi Pisa, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Bar Mocambo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Tree is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Chupiteria ensures a night out tailored to your taste.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 5

Day 5

  • Pisa - Departure day
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  • “Tuttomondo” (Keith Haring)
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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 “tuttomondo” (keith Haring). This beloved art installation is a popular place to see in the city.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Pisa.

Enjoy a lovely meal at Restaurant -Pizzeria Il Mio Capriccio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante alle Bandierine is another top choice with a popular 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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