Classic

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Tuscany

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Classic ~ Tuscany ~

Siena

Medieval, atmospheric & quintessentially Tuscan.

Siena is known for its beautifully preserved, largely pedestrianized historic centre, elegant architecture, and enchanting Piazza del Campo. While it is a popular stop for lovers of art and history, it feels smaller, slower, and noticeably less crowded than Florence, making it a great base for travellers who want a classic Tuscan experience without the intensity of a major city.

At a glance…

Choose Siena if you want:

  • To explore Tuscany with the convenience of staying inside a city, instead the countryside
  • Medieval architecture, hilltop views & dramatic scenery
  • Easy access to some of the most iconic parts of Tuscany, such as the Val D'Orcia  & Chianti

  • 3-5 nights

    Siena is a highly walkable city; you can see most of its highlights in a day, although I do not recommend this! Allow yourself time to linger & wander the narrow, medieval streets, enjoy an aperitivo in the piazza, and get to know Siena.

    If you plan on doing some daytrips outside of Siena to the Tuscan countryside, such as a wine tour, allow yourself the full five nights.

    If you are renting a car then it is worth considering staying even longer to enjoy more of the surrounding countryside.

  • Coming from Florence (recommended):

    1. Fly into Florence airport OR arrive at Florence train station from another leg of your trip

    2. Take a direct train from Florence to Siena (approx 1hr 30mins)

    Note: If you are renting a car, pick up your car rental at the Florence airport & drive to Siena (approx 1 hr 15 mins)

    Alternatively, if not coming from Florence:

    1. Arrive at Siena train station from another leg of your trip

  • Recommended:

    • Walking ✔

    • Public Transit ✔

    • Taxis ✔

    • Car Rental ✔

    • Scooter Rental ✔

    • Late Summer

    • Fall

    • Spring

    • Early Summer

    • Winter - see note below

    Notes:

    In winter you will be trading the warm, sunny days & countryside excursions for Christmas market magic. More on winter in Siena in the Piano Piano tips section below.

    I do not recommend going in the dead of summer, when it gets very hot & incredibly crowded.

  • Classic.

    While Siena is certainly a well-known hub of art & medieval history, it is not as popular of as Florence, for example. Here you will find a good mix of lively atmosphere & authenticity, with accommodations that tend to not book up as quickly & be on the more affordable side.

 

Pairs well with

Tuscan Countryside:

Chianti

Arezzo

Seaside Getaways:

The Riviera

Bay of Naples

What to do?

Have an aperitivo in the Piazza del Campo

Wander the medieval streets, get lost in the narrow lanes, and explore the hidden shops

Visit the Duomo and marvel at the incredible marble floor & Piccolomini Library

  • Climb Torre del Mangia for sweeping views over Siena & the Tuscan countryside

Take a wine-tasting tour out in the Tuscan countryside

Take a day trip by train to San Gimignano or Montepulciano

What’s on the menu?

Some local specialties:

Piano Piano Tips

  • Where you stay in Siena will depend on whether or not you’ve opted to rent a car.

    Those with a car will need to stay on the outskirts of the historic centre, where parking is available. But not to worry; the historic centre is within easy walking distance, meaning that you can enjoy all that Siena has to offer while also having the freedom that a car grants you.

    If you are travelling without a car then I recommend staying within the charming & medieval historic centre. There are a few different neighbourhoods that have different vibes to choose from, but you really can’t go wrong:

    Duomo — quiet, romantic, central
    San Domenico — views, quieter, local feel
    Piazza del Campo — most central, lively, convenient

  • It is important to understand that this will not be the sun-drenched Tuscan escape that most people envision; however, if you’re looking for moody & medieval vibes combined with Christmas markets & traditions then Siena is certainly worth considering.

    I do not recommend renting a car if going in winter, and I also don’t recommend Siena as a stand-alone winter destination. Instead, I recommend starting in Florence, where there is a larger draw for Christmas markets & festivities, and then taking the train to Siena for a more intimate experience.

    Some perks to going in winter: fewer crowds; moody atmosphere; more affordable accommodations; Christmas market magic; mild weather by Northern-European standards

  • Siena is a rare unicorn that can be easily enjoyed with or without a car, and both options have some major perks:

    Siena without a car: The best option for those who want a stress-free experience & plan to stay within the city for the majority of their stay. There are still day trip options that depart from Siena, such as wine tours, that you can easily book to experience the Tuscan countryside.

    Siena with a car: The best option for those who want to stay in city & be close to shops and restaurants, while still having the freedom to explore all that the Tuscan countryside has to offer.

    Since you are most likely coming from Florence I recommend renting your car at the Florence airport, where the surrounding roads are much easier to navigate than roads within the city. Even if you are staying in Florence for a few days first, it is worth getting a cab to the airport to pick up your car.