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

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Hotel
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Description

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, 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, Pisapiazzale MichelangeloBasilica of Santa Croce in FlorenceUffizi GalleryPonte Vecchiopiazza della Signoria
Cathedral of Santa Maria del FioreCentral MarketThe Boboli GardensSiena Cathedralpiazza del Campo
Porta San GiovanniPiazza dell'AnfiteatroGuinigi TowerSan Michele in ForoPiazza NapoleoneSt Martin Cathedral
“Tuttomondo” (Keith Haring)

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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.

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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Jeffer Cocktails & Friends, known for its inviting atmosphere. Le Parisien Wine Bar is another great option if you’re looking for a place to get the night started. Similarly, Las Volta Cocktailbar provides a great setting to enjoy the night away.

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 93 km, 2 hours 12 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • piazzale Michelangelo
  • 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.

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 world-famous places to visit in Pisa. Next, head to Piazza Del Duomo, Pisa, a globally renowned public square, known for its UNESCO world heritage-designated 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 Piazzale Michelangelo. This enchanting observation deck offers a unique experience that is highly recommended. Meanwhile, Basilica Of Santa Croce In Florence adds its own distinct charm to your journey. Finish your day with a visit to Uffizi Gallery, a historic art gallery 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.

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.

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.

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.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 3

Day 3

  • Florence
  • Siena
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Drive 79 km, 1 hour 41 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • The Boboli Gardens
  • Siena Cathedral
  • piazza del Campo
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Florence and Siena, 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 Siena. You’ll stay here for 1 night.

Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Cathedral Of Santa Maria Del Fiore. This spectacular church is an inviting place to see in Florence. Continue your discovery at Central Market, a visually striking food market with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to The Boboli Gardens. This locally renowned botanical garden offers a visually striking encounter with Florence. Siena Cathedral is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 Siena's best restaurants.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 4

Day 4

  • Siena
  • Pisa
  • More

Drive 147 km, 3 hours 11 min

  • Porta San Giovanni
  • Piazza dell'Anfiteatro
  • Guinigi Tower
  • San Michele in Foro
  • Piazza Napoleone
  • St Martin Cathedral
  • More

On day 4 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 San Gimignano and Lucca. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Get ready to discover some of the most iconic wonders in Siena, including a monument, a public square, and a church. Start your day at Porta San Giovanni. This culturally significant monument is a curiosity-inducing place to see in Siena. Then, wander over to Piazza Dell'anfiteatro. If visually striking sites excite you, this public square will be right up your alley. Nearby, you’ll also find Guinigi Tower. This visually striking monument is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, San Michele In Foro is an often recommended spot in the village that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the instagrammable Piazza Napoleone. Take a moment to appreciate the fascinating details of this captivating public square in Siena.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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 and reflect on the day's adventures.

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 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.

Say good night to Pisa and look forward to another great day of your road trip in Italy!

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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, we recommend visiting “tuttomondo” (keith Haring), a detailed art installation before you head out.

Maximize your last day in Italy and go on a shopping spree in Pisa’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

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

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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