(800) 814 COOL Questions? Call Us Now!

Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

1,483 Reviews 4.59 out of 5 stars Based on 1,483 reviews collected by City Boat Tours and TripAdvisor | Recommended by 91% of reviewers |
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Florence, Italy

Loading Options

10 hours 30 minutes (approx.)
Mobile ticket
Instant confirmation

Overview

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.

What's Included

  • Free time in San Gimignano and Monteriggioni Medieval towns
  • Visit to a charming wine estate in the Chianti area with tasting of up to 2-3 Chianti wines
  • Expert multilingual Tour Leader
  • Lunch
  • Gratuities
  • Hotel pickup and drop-off
See 4 moreSee 5 more

Meeting Location

Meeting point

Piazzale Montelungo
Firenze FI, Italy

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

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.

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • 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

Frequently Asked Questions

(7)

Q: What is the cancellation policy for the Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CEST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-6367P15

Traveler Photos

Reviews

4.59
1,483 reviews

Average 4.59 out of 5 stars based on 1,483 traveler reviews collected by City Boat Tours and partner sites such as Cool Destinations and TripAdvisor

5 stars
1,070
4 stars
276
3 stars
90
2 stars
29
1 star
18

Loading Options

Similar Tours & Activities

The Florentine House of the 14th Century: 1 hour tour in the Renaissance life

The Florentine House of the 14th Century: 1 hour tour in the Renaissance life

3
 1 hour  Free Cancellation  Instant Confirmation
from
US$154.75

Pisa and Lucca Tour from Florence with the Leaning Tower access

Pisa and Lucca Tour from Florence with the Leaning Tower access

2
 5 to 6 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
from
US$833.20

Montepulciano and Pienza Tuscany Wine&Cheese Fullday from Florence

Montepulciano and Pienza Tuscany Wine&Cheese Fullday from Florence

New To The Site!
 9 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
from
US$952.33

Best of Florence Electric Bike Tour

Best of Florence Electric Bike Tour

6
 3 hours  Free Cancellation  Instant Confirmation
from
US$70.99

Travelers Who Bought This Tour Also Bought

Chianti Wine Tour from Florence

Chianti Wine Tour from Florence

 5 hours  Free Cancellation  Instant Confirmation
from
US$53.36

Florence Electric Golf Cart Tour

Florence Electric Golf Cart Tour

 90 to 120 minutes  Free Cancellation  Instant Confirmation
from
US$81.69

Pisa and Piazza dei Miracoli Half-Day Tour from Florence
Likely to Sell Out

Pisa and Piazza dei Miracoli Half-Day Tour from Florence

 6 hours  Free Cancellation  Instant Confirmation
from
US$41.55

Cooking Art Brunelleschi

Cooking Art Brunelleschi

 3 hours  Free Cancellation  Instant Confirmation
from
US$69.80

What's Included

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Free time in San Gimignano and Monteriggioni Medieval towns
  • 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
  • Siena tour with professional guide with Headsets (not included in the semi independent option)
  • Lunch
  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets (approx. 7€ pp)

Additional Info

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available
  • 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
  • This tour/activity will have a maximum of 63 travelers

Report Product Issue

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Free Cancellation

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

100% refund
No refund

You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CEST).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Sorting, ranking, and search results

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

City Boat Tours wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through City Boat Tours over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.