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Tuscany 2 Day Itinerary

Tuscany 2 Day Itinerary From Pisa:
How To Spend 2 Perfect Days

Tuscany 2 Day Itinerary

If you’re planning a trip to Italy, you don’t want to miss the Tuscan countryside. You could easily book a guided tour from Florence to Tuscany, it is a popular option.

However the tours are pretty pricey (often $200) and don’t afford you much freedom. It is a good option though if you want a quick hassle free way to get out of the city and see this side of Italy.

But if you are able to drive manual, renting a car in Pisa is as cheap as 30 euros a day!

Take the train from Florence to Pisa

Many trips to Tuscany start in Florence since it’s such a large city. But we found that driving from Pisa was shorter, easier and allowed us to visit the Leaning Tower of Pisa as well!

And depending on which train you take, it’s only about 50 minutes to 90 minutes and as cheap as 8 euros.

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Rent a car in Pisa

We rented with Target Rent at the Pisa Airport. It was 30 euros a day pre-insurance for a Fiat Panda. (They had the best prices in Pisa!)

These cars are tiny so if you’re a family or a group of friends with a lot of luggage, it might not be a good fit. However for 2 people to rent with a small amount of luggage, it was perfect!


Drive 1 hour & 15 minutes to San Gimignano

Hit the road and enjoy the Tuscan countryside! Once you get out of Pisa the roads wind through some seriously beautiful landscapes.

We visited in late October so there were quite a lot of fall colors as well which made the landscape extra spectacular!

Tuscany 2 Day Itinerary

As you draw closer to San Gimignano, you’ll see the iconic view of the skyline, full of historic towers. Hop out of your car to soak in the views and capture some pictures before heading into town!

Tuscany 2 Day Itinerary


Parking

Once you arrive in town, you’ll most likely have to pay for parking. We paid 10 euros for the day at a little lot on the back side of town. (Many of the lots when you first pull in are for residents only!) Be mindful of parking signs and just be ready to pay for a spot if need be.

Sample wines, chocolates, truffles, gelato and pizza

Once you have parked, head into town! San Gimignano is spectacularly beautiful. And as you stroll the mainstreet, you’ll see many signs offering free tastings for wine, truffles, chocolates etc. I suggest you take advantage of these! It’s a fun way to chat with the shop owners and get to sample a wide variety of the local cuisine.

Then go ahead and shop! We bought fantastic bottles of local wine for just 6 euros each and a huge block of aged local cheese for 10 euros. The prices are surprisingly low considering their value!

Tuscany 2 Day Itinerary

And don’t miss a chocolate tasting at Nino & Friend’s.
This chocolate shop is located at the end of the main road near RiccaPizza, where we had lunch! There is a huge chocolate fountain at the front of the store, you can’t miss it. They make a great variety of chocolate desserts using Italian truffles or “tartufo.” Italian truffles grow in the forest and are located using pigs or dogs that sniff them out! They are a more expensive delicacy but get used in many dips, seasonings, recipes or even desserts.

This PBS episode does a great job explaining truffle hunting in Italy!

Climb the bell tower: Torre Grossa

After you’ve had lunch and sampled plenty of food, climb of the bell tower for views over San Gimignano.

Open: Monday to Sunday from 10:00 am to 6:00 pm

Panoramic Viewpoint: Punto Panoramico

One of my favorite spots in town was the panoramic viewpoint overlooking the Tuscan countryside. You’ll see signs in town pointing towards “Punto Panoramico.” Otherwise type it into Google Maps and you’ll be able to find it easily. We took a bottle of local wine and some cheese for a picnic on the cobblestone ledge at golden hour. I highly recommend you do the same! Otherwise there is also a little cafe along the street where you can sit and soak in the views as well.

It’s a popular picture spot so you’ll see tourists coming and going to get a great shot overlooking the valley!

Tuscany 2 Day Itinerary

Spend the night at Antica Dimora

Just 12 minutes away from San Gimignano there is a tiny little bed and breakfast with stunning views overlooking Tuscany. It ranges from about 75-80 euros. (May be slightly higher on weekends during peak season.)

But was a fantastic place to stay, especially for the price! The rooms feel like you’ve just stepped onto the movie set of Under the Tuscan Sun. It is truly a dreamy stay.

Sunrise over Tuscany

In the morning, be sure to set your alarm. The sunrise from Antica Dimora is beautiful.

Walk past the little farm area with goats and donkeys, go past the garden patch (where you may see some meandering cats) and you’ll find a perfect place to see the sun come up over Tuscany.

If you only have one day, I recommend you do the route from Pisa or Florence to San Gimignano and skip Volterra and Collodi.

Day 2: Volterra

After sunrise, enjoy a leisurely morning around Antica Dimora before setting off to the next Tuscan village of Volterra.

Drive 25 minutes

Just a short 25-30 minute drive away, you can either have breakfast across the street from the hotel or wait until you arrive in Volterra.

We opted to do lunch in the charming hilltop town and of course, had more pizza and pasta!

If you’re a fan of the Twilight series, this town is where Edward Cullen goes in New Moon to meet the Volturi. Although for filming, the town of Montepulciano was actually used instead.

Key Sights in Volterra

  • Visit Piazza dei Priori (the main square)
  • Visit the Duomo
  • The Guarnacci Etruscan Museum
  • Admire the Roman Amphitheater and its Archaeological Area
  • The Pinacoteca – Art Gallery

Collodi: the Pinocchio Village

After a fantastic afternoon of wine tastings, scenic overlooks and wandering the winding streets of Volterra, I suggest heading to Collodi. Although there are a lot of little Tuscan villages you could choose from, we decided to head to the birthplace of Pinocchio.

Drive 1 hour and 30 minutes

After a 90 minute drive, you’ll find yourself in the being welcomed to Collodi by a towering Pinocchio statue and several painted murals of the beloved fairytale.

This medieval village dates back to the 12th century. And when you pull into town, it can be pretty confusing where to go.

The picturesque village is only accessible by foot after a steep climb

Park nearby the pizza place Ristorante pizzeria da geppetto located at Piazza Carlo Collodi, 2, 51012 Collodi PT, Italy.

From there, head towards the right. There is a cobblestone footpath that will lead you up into the village. You’ll see it leading up towards the buildings tucked in the hills. And you’ll pass the magnificent Villa Garzoni.

It is a steep climb but worth the views!

Tuscany 2 Day Itinerary
Making the steep ascent through the village of Collodi

As you continue along the path, you’ll eventually reach the residential area of the village which is very quiet and quaint. It’s a lovely place to walk around and take pictures.

Just remember, actual people are living in these homes so be respectful. It isn’t a tourist-y stop at all but very charming and authentic!

Tuscany 2 Day Itinerary
Tuscany 2 Day Itinerary
Tuscany 2 Day Itinerary

If you can time your visit with sunset, I highly recommend watching it from the top of the village. You’ll have great views over the towns below as well.

In town you can also visit the Pinocchio Park in town.

We arrived after it had closed because we didn’t want to cut our time short in Volterra but if you’re interested in exploring the park, I suggest starting your day as early as possible in Volterra then arriving late afternoon to walk around the park.

Drive 45 back to Pisa to drop off the rental car

Once you’ve finished watching sunset, hop in the car and head back towards Pisa. It’s a 45 min drive. We dropped off the key rental car using the key drop box since it was after hours. Either catch a train out of Pisa or plan to spend the night.

We stayed near the city centre but keep in mind, it is difficult to get taxis at night in Pisa. So we actually wound up walking from the rental car place to our accommodation for the night.

Overall, the two days we spent in Tuscany were a dream. Im so thankful I got to see this beautiful part of the country. You’re going to love Tuscany, enjoy!

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Emily Rose

Hi, I'm Emily Rose! In 2018, I sold all my stuff and moved into my suitcase to travel full time and work around the world! Follow along for the best travel jobs, photos to fuel your wanderlust and epic adventures!

2 Comments

  • Marie says:

    Hi there! My husband and I are planning to go to Italy next year October 2022. We are going first to Rome and then next in Florence/Tuscany. We are also planning to drive in Tuscany region and will stay there for 2 days to get the taste of a country side living. My question is, from Rome where do you think is the best way to take the route that is closer to Tuscan region. I want to visit Pisa, Sienna and San Gimignano and ofcourse to do wine tasting. After in Tuscany we are heading to Florence for another 2 days. Hope my queries makes sense to you. Thanks

    • Emily Rose says:

      Hi Marie!! Wow sounds like you will have a wonderful trip 🙂 I’m sure you’re going to fall in love with Tuscany!

      The train system in Italy is so fantastic, affordable and easy to use. If I were you, I would probably take the train from Rome to Florence. It’s an hour and 45 minutes. Then after your time in Florence (which is incredible!! We spent 3 days there) take the train to Pisa. It’s a little over an hour if you take the fast train or 90 minutes for less expensive train.

      Renting a car in Pisa was super affordable and made for easy access to Tuscany! You could of course have a rental car for the entire time, we just found the trains easy to use 🙂

      Have an amazing trip!! Xx

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