Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Relaxation, Nature, and Foodie Train Trip through Tuscany

Viewed by 82 travelers

Day 1: Exploring the Charm of Siena

Siena, Italy

8:00AM

Breakfast at La Vecchia Latteria

Start your day with a delightful breakfast at La Vecchia Latteria, known for its delicious pastries and cappuccinos.
It is located in the heart of Siena, just a short walk from Piazza del Campo.
€10, 1 hour

10:00AM

Visit Siena Cathedral

Explore the stunning Siena Cathedral with its intricate Gothic architecture and exquisite artwork.
Located in Piazza del Duomo at the center of the city.
€15, 2 hours

1:00PM

Lunch at Osteria Le Logge

Indulge in a traditional Tuscan meal at Osteria Le Logge, known for its authentic cuisine and charming ambiance.
Located in Piazza del Lupa, a quaint square in Siena.
€30, 1.5 hours

3:00PM

Explore Piazza del Campo

Stroll around the iconic Piazza del Campo, one of the most famous medieval squares in the world.
Central location, easily accessible on foot.
Free, 1 hour

5:00PM

Travel to Pisa

Board a train to Pisa, enjoying the scenic journey through the Tuscan countryside.
Head to Siena Train Station and take a direct train to Pisa Centrale.
€20, 2 hours

7:30PM

Dinner at Ristorante Il Peperoncino

Relish a sumptuous dinner at Ristorante Il Peperoncino, offering a variety of Italian dishes with a modern twist.
Conveniently located near the Leaning Tower of Pisa.
€40, 2 hours
Find Hotels in Siena

Day 2: Discovering the Beauty of San Gimignano

San Gimignano, Italy

8:30AM

Breakfast at Gelateria Dondoli

Start your day with a refreshing breakfast at Gelateria Dondoli, known for its award-winning gelato and pastries.
Located in the heart of San Gimignano's historic centre.
€8, 1 hour

10:00AM

Visit Collegiate Church of Santa Maria Assunta

Explore the Collegiate Church of Santa Maria Assunta, adorned with beautiful frescoes and offering panoramic views of the town.
Located in Piazza del Duomo in the centre of San Gimignano.
€6, 1.5 hours

1:00PM

Lunch at Ristorante Dorando

Enjoy a delightful lunch at Ristorante Dorando, known for its traditional Tuscan dishes and warm hospitality.
Located near Piazza della Cisterna, a charming square in San Gimignano.
€25, 1.5 hours

3:00PM

Explore San Gimignano's Towers

Take a leisurely stroll through the medieval streets of San Gimignano and admire the iconic tower houses that dot the skyline.
Just wander around the town centre to discover the towers.
Free, 1 hour

5:00PM

Travel to Asciano

Hop on a train to Asciano, enjoying the scenic journey through the rolling hills of Tuscany.
Head to Poggibonsi-San Gimignano train station and take a train to Asciano.
€15, 2 hours

7:30PM

Dinner at Osteria dell'Acquacheta

Savour a delicious dinner at Osteria dell'Acquacheta, known for its rustic Tuscan cuisine and friendly atmosphere.
Located in the heart of Asciano, close to the train station.
€35, 2 hours
Find Hotels in San Gimignano

Day 3: Exploring the Enchanting Town of Asciano

Asciano, Italy

9:00AM

Breakfast at Bar Il Cassero

Start your day with a traditional Italian breakfast at Bar Il Cassero, a local favourite known for its pastries and espresso.
Located near the historic centre of Asciano.
€5, 1 hour

10:00AM

Visit Museo d'Arte Sacra

Explore the Museo d'Arte Sacra, housed in the former Church of Saints James and Christopher, featuring religious art and artefacts.
Located in Piazza del Grano in Asciano.
€7, 1.5 hours

1:00PM

Lunch at Osteria del Borgo

Indulge in a traditional Tuscan lunch at Osteria del Borgo, known for its homemade pasta and regional specialities.
Situated in the historic centre of Asciano, offering a cosy and authentic setting.
€20, 1.5 hours

3:00PM

Explore Asciano's Countryside

Take a leisurely bike ride or walk through the picturesque countryside surrounding Asciano, known for its rolling hills and vineyards.
Rent a bike from one of the local shops or simply enjoy a leisurely stroll through the countryside.
€10, 2 hours

6:00PM

Travel to Pienza

Board a train to Pienza, enjoying the scenic views of the Val d'Orcia region along the way.
Head to Asciano train station and take a train to Pienza.
€10, 1.5 hours

8:00PM

Dinner at Latte di Luna

Enjoy a gourmet dinner at Latte di Luna, offering a modern twist on traditional Tuscan cuisine with stunning views of the Val d'Orcia.
Located in the heart of Pienza, overlooking the picturesque landscape.
€50, 2 hours
Find Hotels in Asciano

Day 4: Immersing in the Beauty of Pienza

Pienza, Italy

8:30AM

Breakfast at La Buca di Enea

Start your day with a delicious breakfast at La Buca di Enea, a charming cafe known for its freshly baked pastries and artisanal coffee.
Located near Pienza's main square, offering a quaint setting to start your day.
€7, 1 hour

10:00AM

Visit Palazzo Piccolomini

Explore the Renaissance architecture of Palazzo Piccolomini, a UNESCO World Heritage Site known for its elegant gardens and panoramic views.
Located in Piazza Pio II in the heart of Pienza.
€8, 1.5 hours

1:00PM

Lunch at Ristorante Dal Falco

Indulge in a gourmet lunch at Ristorante Dal Falco, offering creative interpretations of traditional Tuscan dishes with a focus on seasonal ingredients.
Situated in a historic building in Pienza, providing a unique dining experience.
€40, 1.5 hours

3:00PM

Admire the Views from Pienza's Walls

Stroll along the ancient walls of Pienza and enjoy panoramic views of the Val d'Orcia countryside, a UNESCO World Heritage Site.
Follow the path along the walls for breathtaking views of the surrounding landscape.
Free, 1 hour

5:00PM

Departure to Next Destination

Bid farewell to the enchanting town of Pienza as you head to your next destination, filled with memories of the beauty of Tuscany.
Head to Pienza train station for your onward journey.
€10, 2 hours
Find Hotels in Pienza
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed

Plan Your siena pisa san gimignano asciano pienze Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go