Tour Finder
  1. Home
  2. Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Image 1
Image 2
Image 3
Image 4
Image 5
Image 6
Image 7
Image 8
Image 9
Image 10
Image 11
Image 12
Image 13
Image 14
Image 15
Image 16
Image 17
Image 18
Image 19
Image 20
Image 21
Image 22
Image 23
Image 24
Image 25
Image 26
Image 27
Image 28
Image 29
Image 30
Image 31
Image 32
Image 33
Image 34
Image 35
Image 36
Image 37
Image 38
Image 39
Image 40
Image 41
Image 42
Image 43
Image 44
Image 45
Image 46

Overview

Available languages

Portuguese
English
Italian
French
Spanish

10 hours 30 minutes

Mobile ticket

A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

Additional Info

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

Specialized infant seats are available

Not recommended for travelers with poor cardiovascular health

Travelers should have at least a moderate level of physical fitness

A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements

May be operated by a multi-lingual guide

Please note that the given order of the visits may change

Please inform us of any food intolerance or allergy in advance

Kindly note that the Semi independent option does not include the professional guide in Siena

LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required

HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What‘s Included

Free time in San Gimignano and Monteriggioni Medieval towns

Siena tour with professional guide with Headsets (not included in the semi independent option)

Visit to a charming wine estate in the Chianti area with tasting of up to 2-3 Chianti wines

Expert multilingual Tour Leader

Sampling of wines, extra-virgin olive oil and regional products

Journey by fully-fitted GT Coach with Free Wifi on board

Gratuities

Hotel pickup and drop-off

Siena Cathedral tickets (approx. 7€ pp)

Lunch

What To Expect

The tour starts from Florence and leads you to the atmospheric Medieval gem of Monteriggioni. It was built in 1203 and became a strategic garrison town with its 14 towers, Dante called it the “ring-shaped citadel”. Here you can steep yourself in the past and prepare yourself for the wonders of Siena . Here your local guide will reveal to you its main beauties: the stunning Piazza del Campo, an open-air fish bowl, surrounded by softly-washed Siena stone architectural masterpieces. It really is a showpiece place, worth lingering in and drinking in the richness of the past. Visit Piazza del Duomo and be impressed by the imposing Cathedral, one of the finest achievements of Italian Gothic. Before leaving Siena you will be served a light lunch in a cozy restaurant where, together with genuine Tuscan products, you will savour traditional pastries. After your free time for lunch in Siena, continue on to San Gimignano: the home of the renowned Vernaccia wine. This Medieval town is listed as a UNESCO World Heritage Site, and once you're there you'll see why. The secret lies in its soaring towers that seem like skyscrapers! It is a jewel of art and architecture and also boasts one of the best ice-creams in the world! Here you're free to stroll around or just stop and take it all in. Next, Chianti calls. You will visit a rustic wine estate where, after drinking in the landscapes, you can taste and sip quality wines and try the plonk along with oils and local products. This is a tour made for the spirit and the flesh. A perfect way to mix quality culture and cuisine.

Options

Classic Spanish tour

All inclusive tour in Spanish: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Spanish Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic Italian tour

All inclusive tour in Italian: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic English Tour

All inclusive tour in English : Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic Portuguese Tour

All inclusive tour -Portuguese: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Portuguese - Semi independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic French tour

All inclusive tour in French: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Italian Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

French Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

English Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Reviews

4.55

2,055 reviews

Total reviews and rating from Viator & Tripadvisor

1469
370
131
40
45
  • Well worth it !!

    Chris C,

    Aug 18, 2025

    - Viator

    5.00

    So glad we took the tour. We would never have been able to see all the places, rent a car, be on time, etc. If we hadn't been on an organized tour like this. The guide (short guy with an orange bandana for a flag) was exceptional & and organized our large group very well (and the bus driver as well). Not having to think about any logistics was great after 5 days of having to plan everything. All of the locations on this trip had value. We spent enough time in each place to get a thorough experience without being bored. And also leaving a little for us to come back and see. The walled cities are incredible, Sienna so rich in history, and the wine tasting was very fun. I'd recommend this particular trip without hesitation. They said we would be home by 7, and we were 2' early. Over 20k steps in walking overall, so the time on the air-conditioned bus between locations was welcome to relax out of the sun (94 degrees). Also, the Gelato in San Gimanagno was as good as they said it would be. Four-time world champion in ice cream.

  • Great day with kids!

    Mike L,

    Aug 14, 2025

    - Viator

    5.00

    Great time, busy day but fun! Kids saw and did a lot. They loved the wine tasting and made friends with other kids (and adults) on the trip!

  • Get to know a region...

    Corrado S,

    Aug 8, 2025

    - Viator

    4.00

    Getting to know a region like Tuscany even through a short Tour can serve to return pears more days.

  • Long day but eventful!

    Dameion D,

    Aug 5, 2025

    - Viator

    4.00

    Roberta & Juan Carlos - Siena tour Roberta was great & knowledgeable. It was a long day with a lot to see. The wine tasting at the end was a nice treat. John Carlos our bus driver saved the day when the bus broke down just about 20 mins on our way back to Florence. We were stalled for about 10 mins but during the entire time Juan Carlos never gave up & the bus started again! We arrived back to Florence in one peace and all was well. Thank you Roberta & John Carlos for an eventful evening!

  • Trip to siena ,chianti ,monteriggioni and San Gimignano

    Maria K,

    Jul 21, 2025

    - Viator

    5.00

    Filippa and Gabriel our guides were very friendly to all of us, very well informed about the history of all the places we visited and all the time ready to assist.

From EUR 55.25

4.55
2,055 reviews
Check availability

Related Experiences

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

4.85
SMALL-GROUP Wine Safaris: Chianti, Val d'Orcia and Brunello Tours

SMALL-GROUP Wine Safaris: Chianti, Val d'Orcia and Brunello Tours

4.95
Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-Group Wine Tasting Experience in the Tuscan Countryside

4.91
Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm

Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm

4.97
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

4.95
Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

4.96
Skip the line: Uffizi and Accademia Small Group Walking Tour

Skip the line: Uffizi and Accademia Small Group Walking Tour

4.66
Florence Accademia Gallery Tour with Entrance Ticket Included

Florence Accademia Gallery Tour with Entrance Ticket Included

4.68
Cinque Terre Day Trip from Florence with Optional Hiking

Cinque Terre Day Trip from Florence with Optional Hiking

4.84
Private Golf Cart Tour in Florence

Private Golf Cart Tour in Florence

4.69
Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

4.48
Florence Vespa Tour: Tuscan Hills and Italian Cuisine

Florence Vespa Tour: Tuscan Hills and Italian Cuisine

4.84

Operated by Ciao Florence Tours Srl

A product of Trip Social Group

Australia: Pavel Australia Pty Ltd

Việt Nam: Công ty TNHH Trip Social

top-50

Winner - HO CHI MINH INNOVATIVE STARTUPS IN TOURISM 2022.

Quick links

Destinations

Contact us

  • zalo
  • whatpsapp
  • messenger
Travelling effortlessly, together

© 2025 Trip Social Group. All rights reserved.

    Accepted Payment Methods

  • visa
  • visa
  • visa