How to Spend the Perfect Day in Siena, Italy

Siena, Italy: The Ultimate Guide to the Medieval Tuscan Town

Like you, my head spins at the shear volume of travel recommendations out there.

Here’s what I mean:

The first time I traveled to Siena, Italy, I did a Google search on things to do in Siena.

Google returned a hefty 24,000,000 results worth of Siena, Italy travel recommendations.

Siena Italy Travel Recommendation Search Term

The thing is:

None of them had all three things I was looking: food, wine, and hiking or walking.

So, I made my own Siena travel itinerary and spent an amazing few days in Siena. Keep reading for the best things to do in Siena for the perfect day.

Why You Should Visit Siena, Italy

Siena, Italy is a mid-sized town in the heart of Tuscany. It is surrounded by the Chianti wine region which produces some of the most recognizable and food friendly wine in the country. The walled, medieval town with a pedestrian only town center is compact, lively, and perfect for exploring by foot.

Go to see medieval architecture. And go to taste and smell traditional Tuscan food and Chianti wine.

Piazza del Campo in Siena
The Piazza del Campo in Siena, Italy.

The Palio is a famous horse race held in the town square (Piazza del Campo) twice a year on July 2 and August 16 between representatives of each contrada (city ward). If go in the months leading up to the race you may see and hear contrada bands marching around town to stir up excitement.

Siena Italy Contrade
A marching contrada stirring up interest for the Palio.

My wife and I loved exploring the city on foot while sampling porchetta, glasses of house wine (which was always Chianti), and hearty plates of pasta. When we needed a break, we found quiet, relaxing green spaces around the town.

If this sounds good to you, keep reading for a complete daily agenda with things to do in Siena and an interactive map of where to eat, drink, walk and sight see.

How to Get to Siena, Italy

The closest airports to Siena are Florence and Pisa. Alternatively, you may be driving through Tuscany to Siena from Rome – a truly worthwhile experience. Keep reading below for bus, train, and driving options for each city.

Getting to Siena By Car

Siena is a walled city with a pedestrian town center. Parking lots near the pedestrian zone are pricey (25-35 Euros/day). Park at the Train Station Car Park for just 2 Euros/day.

From the car park, take the mobile escalator to just outside of the city walls. Click below for more details on parking in Siena.

Siena Parking Facilities Map

Tip: Check with your lodging or hotel about their parking options. Some hotels in Siena offer a discounted parking rate.

Approximate Driving Times to Siena:

  • From Florence – 1 hour

  • From Pisa – 1.5 hours

  • From Rome – 2 hours and 45 minutes taking the direct highway route; 4 hours minutes taking countryside roads through Tuscany.

Getting to Siena, Italy From Florence by Public Transit

If you are taking the bus or train to Siena from Florence, the first thing you will need to do is get to the Santa Maria Novella train station. There is a direct tram (T2) that operates from 5 am to 12:30 am (2 am on Fridays and Saturdays) between the airport and the train station.

The ride takes about 20 minutes, costs 1.50 Euros, and runs every 4-18 minutes depending on the time of day. More information on the tram can be found by clicking the link below.

Tram information and tickets here

By Train

There are two trains every hour from Florence to Siena. The direct train takes 1 hour 30 minutes while the other takes 1 hour and 45 minutes. You can use the Trenitalia link below to view train times and purchase tickets.

Train tickets and schedule

By Bus

The 131R bus run by Tiemme departs from the Florence bus station (Firenze Autostazione) near the train station and arrives at the Siena bus stations (Siena-Via Tozzi). The trip is only 1 hour and 15 minutes and costs 8.40 Euros each way if you purchase ahead of time. Tickets are more expense if you purchase on the bus.

You can purchase tickets and view the bus schedule on the Tiemme website below. Remember to validate your ticket in the stamping machine before getting on the bus.

Tiemme bus tickets and schedule

Getting to Siena, Italy From Pisa by Public Transit

The train is the best option to get to Siena from Pisa.

There are two trains every hour from Pisa Centrale train station to Siena. From the airport, take the 5 minute Pisa Mover shuttle to Pisa Centrale. Single tickets are 5 Euros. Tickets and shuttle information can be found at the link below.

Pisa Mover shuttle tickets and info

The train ride is between 1 hour 30 minutes and 1 hour and 50 minutes depending on the train. You will have a changeover at Empoli. You can use the Trenitalia link below to view train times and purchase tickets.

Train tickets and schedule

Getting to Siena, Italy From Rome by Public Transit

There are multiple different options for getting to Siena from Rome airport. Each option will take about 3 hours and 45 minutes. All train tickets can be purchased from the Trenitalia website below.

Train tickets and schedule

Option 1: Train to Siena

Take the train from Rome Fiumicino aiport to Roma Termini. Then take the train to Siena. There will be a changeo Chiusi.

Approximate Length: 3 hours, 45 minutes

Option 2: Train to Florence, then train or bus to Siena

Take the train from Rome Fiumicino aiport to Roma Tiburtina. Take the 1.5 hour train to Florence Santa Maria Novella from Roma Tiburtina. Then see above for directions on getting to Siena from Florence.

Where to Say in Siena

Stay inside of the town walls. The town is extremely walkable (I mean, the center of town is literally pedestrian only) and compact. As long as you are in or near that zone, you will be close to everything.

A few options to consider:

Budget: B&B Il Corso

Splurge: Residenza d’Epoca Campo Regio Relais

Airbnb: Libery Siena Flat

What to Eat in Siena

The food in Siena and throughout Tuscany is incredible. During my first visit to Siena, I had a delicious, juicy pork chop that changed everything I thought pork chops (which was that they are dry, tough, and tasteless – turns out that’s not true!).

Here are a few regional foods not to miss:

Wild boar (cinghiale) sauce – Tuscan version of ragu using wild boar. Get this over a plate of Pici pasta.

Porchetta – Pork loin with spices and herbs, wrapped in pork belly, and slow roasted. Fatty, crispy, and juicy goodness that is amazing on a sandwich.

Panforte and Ricciarelli – Two traditional sweet pastries of Siena.

Ricciarelli Siena Pastry
Ricciarelli – Traditional sweet, biscuit-like pastry of Siena.

Where to Eat in Siena

Here are some of the best places to eat in Siena. Click on the name of establishment to visit their website. When to go to each of these places is in the complete itinerary below.

Breakfast and Snacks

Bar Pasticceria Nannini – Siena institution for breakfast and pastries. There are a few locations through the city. I like the one on Via Banchi di Sopra.

Torrefazione Fiorella – Great cafe and breakfast spot that roasts its own coffee. Go here for the best coffee in Siena.

La Vecchia Latteria – Gelato. Enough said.

Liberamente Osteria – Cafe and bar on Piazza del Campo. Perfect for an aperitivo or cafe while facing the piazza.


La Taverna di San Giuseppe – One of the best traditional Tuscan restaurants in the city. Call ahead to reserve.

Osteria La Chiacchera – Another great restaurant serving traditional Tuscan food. Handwritten menus and rustic interior add to the charm. Plus, the prices can’t be beat.

Il Pomodorino – Sit outside at this pizzeria to enjoy views of the Duomo and nicely charred pizza crust.

Sandwiches and Delis

Gino Cacino di Angelo – Deli with a great selection of meats, cheeses, prepared foods, sandwiches and wine.

Prètto Prosciutteria – Another great deli for meat and cheese snacks, sandwiches, and wine.

Wine to Drink in Siena

Chianti wine and all its designations is all over town. Chianti red wine is dry, medium bodied, and highly acidic. It is a great companion to Tuscan and Italian food.

The wine must be made from at least 80% Sangiovese grapes, but is often 100%. Below are several designations to know and try.

  • Standard Chianti: Aged for 6 months. Dry, young, and acidic.

  • Classico: Chianti wines produced in the Classico sub-region, often considered the region that produces the highest quality Chianti.

  • Superiore: Aged for 1 year. Softer tannins and more developed flavors.

  • Riserva: Aged for 2 years. Some of the best wines in the region.

  • Gran Selezione: Aged for 2.5 years. Premium wines from the Classico sub-region.

Hiking in Siena

My favorite option for hiking in Siena? Exploring the city on foot. We’ll talk about that later though.

For a longer hike through the surrounding countryside, the Via Francigena trail system goes through Tuscany. The trail cuts through Siena and connects it to neighboring towns.

The below hikes are one way so you will need to take a bus to/from the neighboring town depending on where you choose to start your hike. Click the links below for bus schedules to do so.

Hike Option 1: Siena to Ponte d’Arbia, 16 miles

Bus Schedules:

Hike Option 2: Monteriggioni to Siena Hike, 12.8 miles

Bus Schedules:

Siena Italy Countryside
Lush Tuscan countryside on the edge of Siena.

Complete Siena, Italy Itinerary

Siena is perfect for exploring on foot. The town is fairly small, so it can be covered in one full day. This itinerary is the only source you need for food, wine, and walking in Siena.

This daily agenda assumes that you are arriving in the afternoon-ish and are staying in Siena for two nights. But, feel free to modify based on your schedule.

Keep reading for the daily plan!

Arrival Day

After checking in to your lodging option, walk to LaVecchia Latteria for gelato. Spend the pre-dinner hours either walking the old town streets and visiting shops or get an Aperol spritz or negroni at Liberamente Osteria while overlooking the Piazza del Campo.

For dinner, go to Il Pomodorino for neopolitan stlye pizza and an amazing view of the Duomo or Osteria La Chiacchera for simple, Tuscan cooking.

Your Next Day in Siena

Use the Interactive Map below to explore Siena. You will notice that the numbered attractions in the map follow a loop. Visit them in order and you will cover 6 to 8 miles of food and wine goodness.

First off, get your pastry and caffeine at Bar Pasticceria Nannini on Via Banchi di Sopra. Panforte and ricciarelli are two Sienese sweets you should try.

Start your exploration of the city at Basilica of San Francesco and follow the interactive map. There is a path off of Condominio Bardini that takes you down to Fonti di Follinica. Stop for a porchetta sandwich at Gino Cacino di Angelo.

Spend the afternoon checking out the sites near the Duomo. The OPA Si Pass is a great all in one pass that will get you into multiple sites.

Purchase your OPA Si Pass here

For the best Tuscan food in town, go to La Taverna di San Giuseppe for dinner. Make reservations.

Departure Day

Before you leave Siena, take one last walk through town to get breakfast at Torrefazione Fiorella. Grab a sandwich to go at Prètto Prosciutteria for lunch while you travel to your next destination.

Siena, Italy Interactive Map

Ready to Visit Siena?

If you have any questions about this itinerary, please leave a comment! I would also love to hear if you have other suggestions on places to check out in Siena.

Siena is an incredible place for food, wine and walking. Remember my magical pork chop that gave me a whole new perspective? Well, travel is really good at providing new perspectives and changing minds.

See for yourself! Check out this post for How to Plan Your Trip in 6 Steps

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