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Private Tuscany Tour to Siena and San Gimignano with Winery Lunch

icon 10 hours Mobile ticket Free Cancellation
Tickets from € 500.00

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After leaving Florence you will travel toward San Gimignano and enjoy the views of vineyards and rolling hills as you listen to the fascinating history of this town. On arrival your guide will walk you to the main gate and you have free time to roam the picturesque streets and squares. Maybe browse the local shops, try an award winning gelato or walk among the town’s famous medieval towers. Next we stop at an organic, family-run wine estate. You will enjoy a traditional local lunch with plenty of wine, and soak in the idyllic location overlooking stunning views of the surrounding countryside. After lunch, view Siena through the eyes of a local as you join a guided walking tour through the medieval city. Learn about the world’s oldest bank, see the Piazza del Campo - the site of the 600-year-old Palio horse race - and admire the interior of the Duomo, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
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  • Maps of and information about all the towns visited
  • Winery tour and wine tasting of four varieties only for 18+ age old
  • Hearty farmhouse lunch – veggie and gluten-free options available
  • Professional English speaking tour guide with you for the whole day
  • Guided walking tour of Siena with entrance fee to the cathedral
  • Air-conditioned vehicle
  • Free time to explore San Gimignano at your own pace
  • Gratuities
  • Hotel pickup and drop-off
  • Food and drinks, unless specified
Departure Point

Traveler pickup is offered

  • Florence, Florence, Italy
    After meeting your expert guide, an air-conditioned minivan will whisk you away to the first stop of the day, San Gimignano. The drive to San Gimignano will take about 1 hour. During the journey, your guide will explain the itinerary for the day and entertain you with interesting facts about San Gimignano and Tuscany!!!
    15 minutes
  • San Gimignano, San Gimignano, Italy
    San Gimignano is a small, walled Tuscan hill town and a UNESCO World Heritage Site. San Gimignano is most famous for its towers of which there were 72 though there are just 14 remaining today. From this the city gets its nickname of the little Manhattan of Tuscany. Your guide will give you a map and point out the best landmarks, so that you can roam independently the picturesque streets and squares of this enchanting hilltop town.
    120 minutes
  • Piazza della Cisterna, San Gimignano, Italy
    Your guide will lead you to the entrance city gate and that is where the main boulevard starts from, Via San Giovanni. This street will take you to Piazza della Cisterna, the heart of San Gimignano and also the setting for several films. This was the square where festivals and tournaments took place while the Piazza Duomo was the religious and political centre. This is also where the best gelato in the world is – Gelateria della Piazza 'Dondoli'. It's won many awards as the best gelato, you could try it and see what you'll think!
    20 minutes
  • Piazza del Duomo, San Gimignano, Italy
    From Piazza della Cisterna, the next piazza along is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but is well worth visiting! The beautiful interior of the cathedral walls is filled with colorful 14th century frescoes in every space available. You could also climb up one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa) to appreciate the incredible 'BIRD'S EYE' view over San Gimignano.
    20 minutes
  • Rocca of Montestaffoli, San Gimignano, Italy
    Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and It is a peaceful setting with olive trees and the wall surrounding the garden that formed part of the 14th-century fortress Medici of Florence built to protect this town from Siena. if you walk to the back of the garden and climb the steps to the top, the views over San Gimignano's skyline are absolutely breathtaking.
    30 minutes
  • Fattoria Poggio Alloro, San Gimignano, Italy
    After the morning exploration of San Gimignano, a 15-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Visit the farm, enjoy an informal wine tasting lesson and a traditional Tuscan lunch with plenty of wine, in the most gorgeous location overlooking stunning views of the surrounding countryside. Take the opportunity to meet fellow travelers while feasting on fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the opportunity to buy the local products of the winery before heading to San Gimignano.
    120 minutes
  • Siena, Siena, Italy
    After lunch, a 45-minute drive will take you to Siena, a real medieval gem and in fact one of Tuscany's most famous and beautiful hill top towns. When you arrive you will join a 1 hour guided walking tour with a local city guide through Siena's most beautiful streets and sites, including the entrance to the Cathedral, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
    180 minutes
  • Piazza Salimbeni, Siena, Italy
    The first stop on the walking tour of Siena is a bank that has its headquarters in this square - the oldest surviving bank in the world. It's called Monte dei Paschi di Siena and it has been running continuously since 1472. Your guide will explain how Siena's wealth through the centuries came from being on the pilgrim route known as the Via Francigena, a route that led pilgrims between Rome and Northern Europe. Siena prospered as a banking town by lending money and exchanging money for the merchants who were using the pilgrim route as a safe travel route. The Sienese are still wealthy from their banking past and are still famous for their banks today!
    15 minutes
  • Contrada della Torre, Siena, Italy
    Your local guide will then walk through some of the most picturesque back streets of Siena, while telling about something very unique to Siena are the 17 districts which make up the historical centre. The name for these ancient divisions is 'contrade'. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. The sense of identity and belonging to ones 'contrada' is extremely important. They are self-contained little worlds with their own church, where newborns are baptised, and a public fountain where the newborns are baptised a second time! Needless to say there are strong rivalries between these districts, that explodes during the Palio horserace held twice a year in Piazza del Campo.
    15 minutes
  • Piazza del Campo, Siena, Italy
    Piazza del Campo is one of the most beautiful squares you will ever see and it is also the city's gathering place, where the locals meet for a coffee and to chat and of course gossip. The unusual square (actually not a square, it's in the shape of a sea-shell, and sloping!) is the site of the famous Palio horse-race. A 600 year old tradition of Siena. The piazza gets transformed into a racing track twice a year and the contrade, or neighbourhoods of the city battle out for the highest honour possible – winning the palio. You'll hear more about this on the tour, your local guide will set the scene so that you can somehow live for a moment the vibrant atmosphere of this incredible race.
    15 minutes
  • Duomo di Siena, Siena, Italy
    Our walking tour then ends inside the Duomo of Siena – undoubtedly the jewel of the city. If you've seen the interior of Florence's Duomo, it is nowhere near as spectacular as Siena's. The most unique part of this city's cathedral is its floor. It's an artwork on its own, made out of the world's most precious marbles – in fact, it's a combined masterpiece of over 50 images created over 2 centuries by some of Italy's most important artists. Then, enjoy walking through the city center on your own before meeting your guide again!
    15 minutes
  • Florence, Florence, Italy
    After the visit of Siena, a 1 hour and an 15 minute drive will take you back to Florence. You will dropped off at the start point with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
    15 minutes
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
  • Disclaimer: Only 18 years old and above are allowed for wine tasting
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
Vacation34538120444
24 Apr 2023
Tour spettacolare, organizzato benissimo, stra consigliato. Un grazie speciale alla guida Alessandro, il guidatore del bus Giancarlo e in generale all'agenzia. Top!!! Grazie!!!
This tour in Florence is organized by Walkabout Tours

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