4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence

1 / 46
Aerial view at tower of Pisa in Italy on a sunny day.
Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina
4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
4-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence
Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
From A to Z
Travel agent
24/7 fast service

Description

Escape the ordinary with this exciting 4-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. 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 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.

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, accommodations, 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!

Read more

Travel details

Set your travel details to find the best price

Flights

Round trip
Round trip
Travel dates

Travelers

Rooms

Flights

Compare and choose from the best flights to Pisa

Car

Choose from the best car rental deals or see all options

Driver’s age is 30 - 65
I live in
Pick-up: 10:00
Drop-off: 10:00

Personalize your itinerary

Customize tours under each day and destination

Day1

Day 1

  • Pisa - Arrival day
  • More
  • Knights' Square
  • More

Welcome to Pisa, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night discovering what to see in Pisa before embarking on the next leg of your journey.

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. Taking a stroll in the city center is a great alternative. 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.

Enjoy a delicious meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

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 4-day road trip in Italy!

Read more
Day2

Day 2

  • Pisa
  • Florence
  • More

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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Pisa and Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 1 night.

Leaning Tower Of Pisa brings Pisa's character to life. This breathtaking monument is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another breathtaking attraction that never fails to captivate visitors.

Florence’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 1 hour 23 min. Florence welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Basilica Of Santa Croce In Florence. Spend some time admiring the culturally significant features of the church before you continue to your next stop. Then, head to Uffizi Gallery. This top-rated art gallery is a traveler-favorite in the city.

If you're keen to see more, continue to Ponte Vecchio. Feed your curiosity by learning something new about the historical landmark. Next, take your journey to Cathedral Of Santa Maria Del Fiore, an astonishing church.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

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

Read more
Day3

Day 3

  • Florence
  • Siena
  • San Gimignano
  • Pisa
  • More

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, your travel plans include 3 stops at the most scenic, wondrous, and interesting places in the region. Siena, San Gimignano, and Greti are on today's agenda. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 10 min.

Fortezza Medicea (siena) is a curiosity-inducing monument we recommend visiting today. Discover its historic features before continuing your self-guided tour to Piazza Del Campo, an UNESCO world heritage-listed public square that’s well-regarded in the area.

Next, stop by Siena Cathedral, a history-steeped church.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: San Gimignano. Expect your car journey to take a minimum of 42 min. When you arrive in San Gimignano, it's time to take a break from the road.

For a more meaningful self-guided tour of the city's best attractions, visit Porta San Giovanni, an increasingly popular monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’ve had your share of San Gimignano, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Greti. Your travel time is around 51 min.

When you're ready for some sights, head to Villa Calcinaia - Conti Capponi, a locally appreciated winery in Greti. Explore its romantic features at your own pace before you continue your journey.

At the end of the day, you will drive to Pisa, 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 Pisa. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

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

Read more
Day4

Day 4

  • Pisa - Departure day
  • More
  • Palazzo Blu
  • More

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, begin at Palazzo Blu. This underrated art gallery is a hotspot among locals.

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!

Read more

How it works

Book your journey with Europe’s biggest travel platform—expert itineraries, instant confirmation, and full flexibility with 24/7 support.

Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.