Tuscany Itinerary: Pisa, Florence and Siena in 4 Days
Planning a trip to Tuscany and wondering how to see the highlights without feeling rushed? This 4 day Tuscany itinerary covers three of the region’s most iconic destinations — Pisa, Florence, and Siena — in a way that balances sightseeing with time to slow down and soak up the atmosphere.
With excellent train connections and short travel distances between these three destinations, we found it surprisingly easy to explore multiple cities in one trip. Whether you’re travelling as a couple, solo or with family, this itinerary is designed to help you experience Tuscany without the stress.
Tuscany Itinerary Overview
The itinerary is planned to give you 4 full days in Tuscany with 1 night in Pisa and 3 nights in Florence. Day 5 is a travel day back home.
Day 1: Fly Into Pisa and explore the city. Overnight in Pisa.
Days 2-3: Travel to Florence. Explore Florence over 2 days.
Day 4: Day trip to Siena from Florence. Overnight in Florence or Pisa.
Day 5 : Fly back from Pisa or Florence.
Our section just below on How to Travel around Tuscany gives information on getting between these places.
Who this Itinerary is Perfect for
- Couples looking for a cultural European break
- Mid-life travellers who prefer a slower pace
- First-time visitors to Tuscany
- Travellers who want a mix of iconic sights and relaxed exploring
How to travel around Tuscany
Getting between Pisa, Florence and Siena is straightforward. For this itinerary, trains are the easiest option, as there is no worry about driving or parking in these major cities.
- Pisa → Florence: 50 minutes by train
- Florence → Siena: 1–1.5 hours by train
Italian Trains are cheap and reliable. And if you need to change your train time, most tickets are flexible so you can change for no extra cost!
🎒Our Tip: Download the Trenitalia App which will allow you to buy tickets, view schedules and use digital tickets on your phone or just buy from their website.
🔍 Click Here to Book Italian Train Tickets
Day 1 – Exploring Pisa
We start our Tuscany itinerary in Pisa which is a city that’s easy to explore. Upon arrival at Pisa airport, it’s a 10 minutes journey into the city. The main highlights can be seen in half a day.
Highlights :
- Leaning Tower of Pisa
- Piazza dei Miracoli
- A walk along the River Arno
🎒Our Tip: Flights to Pisa are much cheaper than Florence so it makes sense to fly in and out of Pisa. You will save quite a lot of money this way.
The best way to see Pisa is to walk. Join a locally guided walking tour such as this one Pisa City Walking Tour.
The river Arno, runs through Pisa. Ponte di Mezzo also known as ‘Middle Bridge’ links the north and south side and of course it is more or less in the centre of the city.
If you stay in the North side, like we did, you will cross this bridge. Along this bank you will find Palazzo Blu (Clue Palace) which houses the Museum of Art and Culture in Pisa with over 300 works of art.
There are many palaces in Pisa. I really liked the Palazzo della Carovana palace which stands on Knight’s Square. In fact, in this square there are many beautiful buildings. The Palazzo del Consiglio dei Dodici (Council of the Twelve Palace) of renaissance style is also here.
It’s really easy just to wander around here, admire the buildings and stop for a coffee, drink or a pizza – we did all three!. Did you know that the great scientist Galileo’s hometown was Pisa?
Does the Tower really Lean?
The Leaning Tower of Pisa is such an iconic landmark. I’ve seen it in travel brochures, on children’s jigsaws; on travel shows, so I was really excited about going to the square it is situated on and finally seeing it myself.
After St. Peter’s Square in Rome, it is the most visited square in Europe.
In addition to the tower are four key buildings said to represent the four stages of human life: the Pisa Baptistery (birth); the Duomo di Pisa (Cathedral -life); the Hospital of the Holy Spirit (illness) and the Monumental Cemetery(death).
🎒Our Tip: Buy your ticket in advance and choose your time slot. The office is just across the lawned area and well signposted.
There are cafes around and tourist shops to potter in. Closer to that time – around 20 minutes before – you could start queueing to get in. Last time we only queued for 15 minutes.
You are not allowed to take rucksacks in – only cameras or phones seem to be allowed. Ticket prices vary depending upon which buildings you want to explore. Check the link for prices.
Facts About the Tower of Pisa
It really does lean! A few facts curtesy of Wikipedia : the height of the tower is 55.86 metres on the low side and 56.67 on the high side creating a tilt of 3.97 degrees. It underwent a lot of stabilization work in the 1990s as the tilt was increasing over 5 degrees.
There are 297 steps to climb to get to the top and it really does feel weird when you first stand inside. Believe it or not, you do feel the lean!
The climb doesn’t take long but of course the marble steps are winding and steep. From the top there are wonderful views of the city and the tower bell is most impressive.
Unfortunately, rain arrived as we entered the tower but it didn’t deter us. The tower climb/entry slot time is around 45 minutes in total.
Overall, we spent a couple of hours here in the square so it’s perfectly doable if you are here for a day. You definitely need good walking shoes though as the marble on the steps have no grip on them.
After a busy day exploring, enjoying a bottle of chianti and fresh bruschetta with pasta was well deserved. I really enjoyed Pisa and would certainly recommend you spend a day here.
Day 2 – Exploring Florence
The following morning, we continued on our Pisa Florence and Siena 4 Day Itinerary by catching the train to Florence; the destination station is Firenze Santa Maria Novella. Within the hour, we arrived.
🎒Our Tip: Use google maps to locate your hotel from the station and follow those directions.
We recommend the Rapello Hotel in Florence. This is a small boutique style hotel with 26 rooms. Location wise it is excellent; also clean and breakfasts are delicious.
Florence is an incredible city. In fact, some call it the jewel of the Renaissance. Dominating the skyline is the iconic Duomo cathedral which really is breath-taking no matter how many times you see it.
Its gothic appearance is memorizing; its scale and attention to detail, just incredible. You can climb to the top for panoramic views of the city and surrounding countryside but do be prepared to for crowds at peak times.
🎒Our Tip: Purchase a Firenze City Card in advance if you intend to visit a number of museums and galleries.
Day 3 – Florence
There are so many museums and art galleries to visit, roof top terraces and numerous squares to sit and watch the world go by. We came here just wanting to soak up all the atmosphere and that is what we did.
It is very easy to walk around; cobbled streets lead onto more incredible buildings, bustling cafes, pizzerias and markets selling leather goods especially bags!
- Florence Cathedral (Cattedrale di Santa Maria del Fiore)
- Giotto’s Bell Tower (Campanile di Giotto)
- Dante House-Museum (Casa di Dante)
- Bargello National Museum / Palazzo del Popolo
- Piazza della Signoria (Signoria Square)
- Palazzo Vecchio (Old Palace)
- Uffizi Gallery
- Ponte Vecchio (Old Bridge)
- Palazzo Pitti
- Fort Belvedere (Forte di Belvedere)
- Piazzale Michelangelo
- San Miniato al Monte
Best Bridge Views in Florence
If you like shopping, there are plenty of big-name fashion stores as well as smaller independent shops tucked away in the narrow maze around the Duomo and surrounding squares.
Quaint jewellery shops lie on either side of the beautiful Ponte Vecchio bridge. It’s a great photo spot especially at the sun sets with the bridges of the city all in the background.
Another great place for both sunset and city view photos is Piazzzale Michelangelo. This is about a 15 minute walk uphill from the centre. At each turn, the view gets better.
At the top, stalls selling your typical souvenirs sit on the square (very reasonable prices considering the location). We walked up one morning, had an excellent cup of coffee there and marvelled at the view before us.
Pizza, Pasta, Prosseco
Let’s face it – you’re in Italy so there is no point in trying to count calories during your time in Pisa Florence and Siena!
Faced with so many restaurants on every Florence street corner to choose from, wine bars, cocktails, ice-creams… you are not going to go hungry.
We found prices reasonable – certainly cheaper than in the UK for a meal with starters, main course and wine. The choice is yours so take a good look around and you will definitely find something to whet your appetite. We really enjoyed the pizzas!
Day 4 – Trip to Siena From Florence
Siena is only 90 minutes by train from Florence so it’s a great choice for a side trip. We booked tickets online (20 euros return).
Siena’s historical centre is a UNESCO World Heritage Site and as soon as I saw it, I could see why. It is a medieval city with these incredible passage ways and walls right around it.
It’s appearance is very gothic and quite a contrast to the renaissance splendor of Florence. The day we went, it absolutely poured – I mean torrential! The rain only added to the gothic atmosphere.
We along with many others sought refuge at one of the many cafes and restaurants in the main square and we whiled away the hours with a prefect glass of Chianti!
Fly to Pisa or Florence Airport?
However, with the city of Florence being the main draw, flights to this airport can be pricey even out of season. A great alternative is to fly to the city of Pisa.
You can then combine the two cities using the efficient Italian rail service to link you between them. We did just that visiting Pisa, Florence and Sienna over 4 days.
Flying into Pisa is easy from the UK with frequent daily flights from both London and regional airports. Our tickets with Ryanair which included 10KG baggage, priority boarding and specific seat reservations cost less than £70 each.
I booked them about 5 weeks in advance. A comparison for the same dates, baggage etc to Florence would have cost £200 each – you do the maths! We arrived within 2 hours from London, Stansted.
Pisa Airport to City Centre
Once in Pisa airport, you can buy a ticket for the Pisa Mover Shuttle Train to take you into the city centre. This train platform is just a few minutes walk from outside the airport – it’s very well signposted. You can purchase the ticket on the shuttle platform for 5euros one way or double that for a return.
It is then only a 5 minute journey into Pisa Centrale. If you want to go straight to Florence, you can buy your onward ticket via trainline. It will cost you less than 10 euros. Trains generally run every hour and take around 1 hour. It really is very easy and a huge saving.
We however, decided to stay a night in Pisa. It makes sense if you are flying into the city to at least look around and of course, you can’t go to Pisa and not visit the famous leaning tower!!
I wasn’t sure exactly what to expect of Pisa; I had read that it’s was a bit run down and that there wasn’t much to do. However, we tend to feel it’s good to give a place a go and make up your own mind.
Where to Stay in Pisa
We stayed in a great central hotel called Hotel Bologna – less than 10 minutes from the station. Our room was really comfortable and breakfast the next morning was excellent with a fabulous choice of both hot and cold food, fruit, cakes, pastries and of course Italian coffee.
Staff were both friendly and helpful. They also offered an airport taxi collection – an alternative if you don’t want to take the PisaMover. There are lots of hotels around but this one was a perfect base to explore from and very reasonably priced.
See More of Italy
From our many trips to Italy, we feel that if you are limited for time, consolidate your trip in one region.
However, if you have more time here is our Italy by Train Itinerary for a 2 week trip from Venice to Capri to consider.
An alternative is to combine Tuscany with the sparkling island of Sicily at the south of Italy. Plan a trip here with our 6 days in Sicily Guide covering the 2 main cities of Taormina and Palermo.
Buon viaggio!
