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Ciao Florence Tours · Florence

Three towns and a tasting

A long coach day from Florence to Monteriggioni, Siena and San Gimignano, with one wine estate at the end. Pick it for the towns: it's the cheapest way to see Siena with a guide, and the tasting is a bonus rather than the point.

Siena, San Gimignano & a Chianti Winery

About this experience

Be honest with yourself about what you want. This is a sightseeing day with a glass at the end. You get about an hour inside the walls of Monteriggioni, three hours in Siena (a guided walk with headsets from Piazza del Campo to the cathedral, then free time), an hour in San Gimignano, and finally one winery with two or three wines and snacks in the hills outside town. One of the operator's own photos shows the cellar shop at Agricola Poggio ai Laghi near Monteriggioni. Neither area is in the Chianti Classico zone.

Two costs aren't in the price: lunch, and the Siena cathedral ticket (the listing says about EUR 7). The guide offers a group lunch at a set restaurant in Siena. Guests are split on it; some loved the pasta, others say take the time and find your own place on the side streets.

With 3,600 reviews and a 4.7 rating, it runs well for what it is. The complaints are about scale: groups of 50 to 70, headsets that fail, a guide switching between three languages, and a winery stop that some call a sales pitch. If wine is your reason for going, the semi-private day with San Gimignano keeps the town and gives you two wineries and a long lunch.

  • Guided walk in Siena from Piazza del Campo to the Duomo
  • Free time in San Gimignano and inside the walls of Monteriggioni
  • One Chianti estate with 2 to 3 wines and snacks
  • The lowest price for Siena and San Gimignano in one day
  • Free cancellation up to 24 hours before

How the day runs

  1. MorningMeet at Piazzale Montelungo

    The tours and news kiosk at the bus terminal, 5 to 10 minutes on foot from Santa Maria Novella. Staff wear fuchsia Ciao Florence jackets.

  2. About 1 hourMonteriggioni

    Free time in the walled hamlet. Guests report anything from 30 minutes to an hour. Walking the wall costs extra.

  3. About 3 hoursSiena

    A guided walk with headsets from Piazza del Campo to the Duomo, then free time and the optional group lunch.

  4. About 1 hourSan Gimignano

    Free time to wander the towers. Gelateria Dondoli, on the main square, is a listed stop.

  5. About 1 hourThe winery

    Two or three Chianti wines with snacks in the hills outside San Gimignano, and a shop.

  6. About 1 hourCoach back to Florence

    Drop-off at Piazzale Montelungo, about 10.5 hours after you left.

Piazza del Campo in Siena with the Torre del MangiaA straw-covered fiasco of Chianti beside a glass of red and bruschettaA tour group in a winery shop with stacked barrels

What's included

Included

  • Guided Siena walk with headsets (not in the "+ Free Time" option)
  • Free time in San Gimignano and Monteriggioni
  • One winery with 2 to 3 wines and snacks
  • Coach with Wi-Fi from Florence and back
  • Multilingual tour leader

Not included

  • Lunch
  • Siena cathedral ticket (about EUR 7)
  • Hotel pickup
  • Gratuities
  • Water on the coach (guests report EUR 1)

Who it suits

Book it if

  • You want Siena and San Gimignano without renting a car
  • You're on a budget and fine with a big group
  • You want a glass of wine, not a wine lesson
  • You travel with kids: no age limit for the towns

Skip it if

  • Wine is the main reason for your day
  • You walk slowly or need short distances: the coach parks some way from each centre
  • You want an hour or more at a winery
  • Big groups and headsets put you off

What guests say

★★★★★

Combining Sienna, San Gimignano and Monteriggione into one day provides plenty to see and do without spending so much time on a bus. They provided the option for a group lunch at a prearranged restaurant. It was one of the best pasta dishes of our 7 days in Tuscany.

nocall · Dec 2024
★★★★★

It’s a long day but totally worth it! We were a large group of over 70 people and while I did feel a little silly following our guide in Siena wearing headphones I found the tour to be very interesting and helpful information for understanding the city better.

Kallyn_R · May 2024
★★★★★

It was nice to arrive at our first hill town early, before other tour buses got there, as it is a very small town. [...] I’ve read other reviews that found the winery their tour visited was disappointing. Our winery stop was very good.

Noah_C · Apr 2024
★★★★★

Not for anyone with mobility issues as the bus parks some way from each centre and there are a good few steps to negotiate. Wine tasting was a good laugh. An appropriate amount of time at each stop.

David_W · Nov 2023

Tips before you book

  • Budget about EUR 7 for the Siena cathedral ticket and money for lunch. Neither is in the price.
  • Skip the group lunch if you'd rather use the time in Siena: guests say it frees up the afternoon.
  • Test your headset at the first stop. Several 2026 reviews mention sets that didn't work.
  • Expect a sales pitch at the winery. Nobody has to buy, and the prices are higher than in a shop.
  • In November to March only English and Spanish are guaranteed; French, Italian and Portuguese need at least 4 people.

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Frequently asked questions

Is lunch included on the Siena and San Gimignano day tour?

No. You can join a group lunch at a set restaurant in Siena and pay there, or eat on your own. The only food in the price is the snack plate at the winery.

How long is the wine tasting?

About an hour at one estate, with two or three Chianti wines and snacks. One guest timed it at 50 minutes. It is the last stop before the coach back to Florence.

Do you go inside Siena cathedral?

Only if you buy a ticket during free time. The guided walk ends at the Duomo, and the listing puts the ticket at about EUR 7. Tickets are sold on the official Opera del Duomo site.

Is this a Chianti Classico tour?

No. Siena, San Gimignano and Monteriggioni all sit outside the Classico zone, and so does the winery. If you want Gallo Nero estates, look at the Classico half day.

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A guided walk in Siena, free time in San Gimignano and Monteriggioni, and a Chianti estate with two or three wines.

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A guided walk in Siena, free time in San Gimignano and Monteriggioni, and a Chianti estate with two or three wines.

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