Siena & History

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• J

  Jose

  Asked on February 15th, 2026

  how much time spent with guide and how much free time?

  Tour Details
  • 

    Tuscan EscapesOperator•Written February 2026

    Our shared group sight-seeing tours combine free time to expore towns with convivial moments with the whole group: we operate tours in 9 seater vehicles with a local, English speaking guide so there are a maximum of 8 persons on tour.
    
    Our San Gimignano and Volterra tour includes the drive north to the medieval fortress of Monteriggioni (30min stop) and to the UNESCO protected San Gimignano (1h15min) before a farm lunch with wine. In the PM, we visit an alabaster craftsman in his workshop (20mins) as well the town of Volterra (1h) before the final return to Siena.
    
    The guide will explain about the towns and what to do or see there, local history and traditions during transportation between stops. The farm produces saffron and extra virgin olive oil, so you get to learn more about these cultivations while tasting the local products.
    
    The Pienza and Montepulciano Tour is similar, as we take the scenic drive through the Crete Senesi with a 30min coffee stop enroute to the UNESCO protected city of Pienza (1h15min) before a dairy farm lunch with wine. In the PM, we enjoy a cellar tour and tasting of the Vino Nobile before exploring Montepulciano (1h).
    
    Each traveler can choose how to spend their time visiting the towns, as some are keen to visit all the sight-seeing sites and churches while others like to shop. There are always places to sit and watch the world go by!
  • J

    Jose

    Traveler•Written February 2026

    how much free time is given to passengers as opposed to guided? We Do Not Want to Sit and Watch the World Go by. Can you indicate in hours free time?
  • 

    Tuscan EscapesOperator•Written February 2026

    Our sight-seeing tours include time as a group (in the van, stopping for a coffee, having lunch, afternoon activity of tasting wine or seeing alabaster demonstration) as well as free time in the hilltop towns, where each participant is free to explore on their own. The guide provides tips on what to see and where to go, but each traveler ultimately decides what to do with their time in the towns, so the guide merely provides a meeting point and time.
    
    Our San Gimignano and Volterra tour includes a 30min stop at the medieval fortress of Monteriggioni and 1h15min in the UNESCO protected San Gimignano. There is also about 50mins or 1h of free time in Volterra (after the group visit to the alabaster craftsman in his workshop, which usually lasts 20mins) The Pienza and Montepulciano Tour is similar and includes a 1h15min sight-seeing stop in the UNESCO protected city of Pienza before lunch and about 1h in Montepulciano after the group wine tasting (optional, about 20mins).
    
    Please note that San Gimignano, Volterra, Pienza and Montepulciano are all are pedestrian only hilltop towns, so once you are dropped off at the city gates, it is a very short walk along the the main street to reach the main square and not much further wo visit the town's main church and other interesting buildings and sites which are always at walking distance. In Montepulciano (which is the largest and steepest!), we drop you off in Piazza Grande which is the main square at the top of the town so that you can walk down the main road to Porta al Prato, which is the city gate at the bottom of the town. This way, travelers do not have to walk back up the main road again to return to where they were dropped off, so it's a convenient, one-way downhill visit.
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• E

  Ellen

  Asked on June 11th, 2025

  Can you help with booking airfare and transportation to and from the airport?

  Flights / Transfers

  Transport
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    Tuscan EscapesOperator•Written June 2025

    we are an incoming tour operator based in Siena, Tuscany, so we can certainly assist you with travel from the airport to Siena as well as providing accommodation and tours in and around Siena. Unfortunately we do not book plane tickets so we cannot help you with airfare.
• J

  Julie

  Asked on February 28th, 2022

  We are looking to travel in Italy in September 2024. We are thinking of touring the Tuscany region with our homebase in Siena. what do you think the cost would be for a trip in 09/2024?

  Price / Availability

  Tour Details
  • 

    Tuscan EscapesOperator•Written February 2022

    We operate shared group tours daily out of Siena, these are full-day tours inclusive of farm lunch and wine tastings held in 9seater vans and the cost per seat ranges between €140 and €160 depending on the itinerary and inclusions. We also offer packages of these tours that are inclusive of hotel accommodation. There are accommodation options at different standards and pricing, just as there are many different dining options in Siena, from €20 to €100 meals. We don't think the price of our tour package (shared group tours + hotel accommodation) will increase much in the upcoming 2 years but just to be safe, you should consider 10% more compared with the current pricing. Also, we can extend the stay (include other tours) and search out a less expensive accommodation option for you so that you get more time and tours for your funds!