TUSCANY BY TRAIN : 3-day itinerary
Tuscany by train : 3-day itinerary
In this 3-day Tuscany itinerary, you'll find everything you need for a perfect trip: transportation details, interesting facts about each destination, a list of things to do, the cost of each activity, suggestions for where to eat and stay, and a selection of great activities I've handpicked for you on GetYourGuide!
DAY 1 : FLORENCE - CERTALDO - POGGIBONSI
Start your journey from Florence in the morning and head to Certaldo. In the afternoon continue to Poggibonsi, where you will spend the night.
Train:
Florence SMN - Certaldo : the journey takes 52 minutes and the ticket costs €6,90.
Certaldo Alto, also known as 'Castello' is a beautifully preserved medieval village nestled in the Tuscan countryside. From Certaldo Alto, you can spot a glimpse of San Gimignano, a future stop on this itinerary. Certaldo is a perfect place to immerse yourself in the authentic Tuscan atmosphere. The village is still relatively undiscovered by mass tourism, making it a peaceful and pleasant sport for a leisurely stroll!
The small village is famous for its narrow cobbled streets, panoramic views and its rich history, including the birthplace of Giovanni Boccaccio, one of the most famous author in Italy!
The best way to get to Certaldo Alto, the historic center, is by taking the funicular. The round-trip ticket costs €1,70. I suggest you taking it because, even if it's a short ride, it's something worth trying here as it offer great views! Alternatively, for those who prefer walking, you can hike up via Costa Alberti, via del Castello or via Costa Vecchia.
What to do in Certaldo?
- Palazzo Pretorio
- Boccaccio's House
- Museum of Sacred Art
- Church of Saints Jacopo and Filippo
- Stroll through the streets to admire the view
Where to eat?
Look for a traditional trattoria where you can try the local speciality, the onion soup!
In the afternoon, take the train to reach the second stop : Poggibonsi! The journey takes just over 10 minutes and costs €2,80.
What to do in Poggibonsi?
- Poggio Imperiale Fortress
- Fonte delle Fate
- Archeodrome
Where to eat?
In the evening you can relax at a restaurant and enjoy a traditional ribollita, a Tuscan soup! If you already tried it for lunch, opt for a platter of local cold cuts and chesses instead! You won't be disappointed!!
Where to stay?
I stayed in a lovely Airbnb near Piazza Fratelli Rosselli, just 5 minutes from the train station. It cost around €70,00 per night for an entire apartment. But if you prefer a hotel, you can find one for around €100,00 per night.
DAY 2 : POGGIBONSI - SAN GIMIGNANO - SIENA
Depart Poggibonsi in the morning for San Gimignano and travel to Siena in the late afternoon to spend the night there.
To go to San Gimignano from Poggibonsi you need to take the bus 130 near the train station. The ticket costs around €3,00 and the journey lasts about 20 minutes! The bus will stops at Piazzale Montemaggio, near Porta San Giovanni, one of the main entrances to the historic center and from here you can already enjoy a breathtaking view of the Tuscan hills!
San Gimignano is a medieval fortified village known for its iconic skyline of towers that once symbolized the wealth and power of its noble families. The "Manhattan of the Middles Ages" originally boasted 72 towers and only 14 remain today! It's located in the heart of Tuscany and is also renowned for its charming streets, historic piazzas, and world-class gelato. I really love to come back here!
What to do in San Gimignano?
- Piazza del Duomo : Collegiate Church of Santa Maria Assunta, Palazzo Comunale and Torre Grossa (which houses the Municipal Art Gallery)
- Piazza della Cisterna
- Torre dei Becci
- Via degli Innocenti
- Medieval Fountains
- Church of Sant'Agostino
I recommend getting the San Gimignano Pass, which gives you access to the Cathedral and Civic Museums for €17,00. It includes entry to several must-see sites, such as the Cathedral, Museum of Sacred Art, Torre Grossa, Archaeological Museum and more!
Panoramic points:
- Piazzale Montemaggio
- Porta San Matteo (parking area)
- Via degli Innocenti
Where to eat?
For lunch, I ate at a restaurant called "Ristorante la Griglia" which offers a stunning view of the hills! I had a risotto for €15,00, prices are reasonable and I highly recommend it for the view!
Trip to Siena :
Take Bus 130 back to Poggibonsi train station, then a train to Siena which lasts 25 minutes and costs €3,90.
Where to stay?
DAY 3 : SIENA -FLORENCE
Explore Siena in the morning and afternoon. Return to Florence in the evening.
Siena is a medieval city steeped in rich history. At its heart lies the iconic Piazza del Campo, a shell-shaped square that comes alive during the Palio, the horse race held twice a year. Siena also houses one of the most beautiful Duomos in Italy! It's a city I've visited many times and every time I visit, I discover something new and I can't help but fall in love with it all over again! Siena is a must-see when visiting Tuscany!
What to do in Siena?
- Piazza del Duomo : Siena Cathedral, Museo dell'Opera del Duomo, Facciatone (for panoramic views)
- Piazza del Campo : Torre del Mangia, Palazzo Pubblico
- Medici Fortress
- Basilica of San Domenico
- Basilica of San Francesco
Where to eat?
- Osteria Pizzeria Il Vicolo : it's a restaurant I really enjoyed, where I had the famous Bistecca alla Fiorentina!
- Re Artù, just a few meters from Piazza del Campo, serves delicious risottos!
If you prefer to eat a focaccia, there are plenty of nice sandwich shops throughout the historic center!
Train :
Siena – Florence : the journey takes a few more than 1.5 hours and it costs €10.20.
I’ve selected some activities to do in San Gimignano and Siena on GetYourGuide that I find interesting and that can enhance your experience in Tuscany. You can book them directly through the links below ⬇️
Step into the past with a visit to the Campatelli Home and Tower ! This beautifully tower house offers a unique glimpse into the life of a noble Tuscan family !
Explore San Gimignano on a 2-hour private walking tour with a local expert ! Stroll through Porta San Giovanni, Piazza della Cisterna, Piazza Duomo, where you can visit the Town Hall, Picture Gallery and Great Tower (optional with an extra fee).
Discover the legend of the Devil’s Tower, admire the panoramic views from Rocca di Montestaffoli and treat yourself to a world-famous gelato in the heart of the city ! A must-do experience to uncover the history, secrets and charm of this medieval gem !
Discover Siena’s history and architecture on a 2-hour guided walking tour in English with a local ! Visit the Basilica of San Domenico and the city’s UNESCO-listed historic center, learn about St. Catherine, the Palio horse race and Siena’s traditions. And skip the lines to explore Siena Cathedral or Duomo !
Discover Siena on a guided walking tour in English, with skip-the-line access to the Cathedral! Enhance your experience with the OPA SI Pass, which gives you access to the entire Cathedral Complex, including the Crypt and Museum.
Save time and skip the line to visit Siena Cathedral and Piccolomini Library ! This ticket includes an audio guide !
With this ticket you can enter the Palazzo Pubblico, located in the main square, and visit the Civic Museum !
Make the most of your visit to Siena’s Cathedral Complex with the OPA SI PASS which includes entry to the Duomo, Baptistery, Crypt, Piccolomini Library, Museo dell’Opera and access to the Facciatone viewpoint.
Total cost of the trip :
- transportation : €31,50 (train, bus, funicular)
- accommodation : Around €160 (price may vary depending on your choice of lodging)
Total for Transportation and Accommodation: Around €190.00
Optional Expenses (Activities):
- Museums in Certaldo: €7.00 (for Palazzo Pretorio + Boccaccio's House + Sacred Art Museum)
- San Gimignano Pass: €17.00 (includes access to several attractions)
- GetYourGuide Activities: prices vary depending on the activities you choose.
If you decide to visit some museums and monuments, you can expect to spend around €50.00.
Total Approximate Cost for the Trip (without food): €240.00
Food: the total cost for meals is not included, as this will depend on your personal preferences and where you choose to eat.
I’m Carla, a travel photographer and content creator !
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