San Gimignano, Tuscany

Discover San Gimignano — Private Tours, Experiences & Custom Travel

Overview

San Gimignano is a central town in the region of Tuscany, Italy and it is one of the more famous Tuscan towns known to many as the "Manhattan" of Tuscany. This is because approaching San Gimignano from any direction, you will see first that it cascades down a small hill about 325 meters high, overlooking the Val d'Elsa. Then you will wonder about the many "skyscrapers" that dart upward mostly near its uppermost reaches. This is the Town of the Towers, one of the prettiest, most well-preserved medieval towns in all of Italy.

There is evidence that San Gimignano began as an Etruscan settlement as long ago as 500 BC. Later, it was a Roman town on the Via Francigena, between Siena to the south and Lucca to the north. Nothing of moment seems to have occurred during the Roman period, except, during the fall of Rome, when, according to legend, the Bishop of Modena (whom later became Saint Gimignano for whom the city is named) saved the city from barbarian invaders.

So, how to explain the towers? A little history will help.

During the early Christian era, San Gimignano was one of several villages under the domination of the Bishop of Volterra. Toward the end of the 9th Century, the Bishop granted the town the right to hold a weekly market, setting the town on a course of growing importance in the area. In 949 AD, San Gimignano became a city and by 998 AD, the citizens had erected the first ring of walls there. Noblemen and commoners alike built within these walls to take advantage of the protection they offered.

For a period of about three centuries from these early days, there was conflict between the Bishops of Volterra and the local nobility and wealthy signori of the city, with power shifting back and forth between the Bishop's faction (the Guelphs) and the faction identified with the Holy Roman Emperor (the Ghibellines).

In 1199, at a time when the Bishop had once again asserted control he shrewdly offered a tax incentive to noblemen and wealthy merchants who built within the city walls, a second set of which were built a couple of years later.

At the same time, cultivation, harvesting and exportation of saffron and crocuses on the slopes of the Val d'Elsa, was generating great wealth for land owners now living in the city. Within the confined space circumscribed by the walls, the wealthy families competed with one another to display their wealth, resulting in the building of the first towers to overcome the lack of space on the ground. These wealthy families also funded the building of various piazzi (court yards or squares), churches and various other public buildings still extant in San Gimignano today.

So intense was the tower-building competition, that a local ordinance was passed to prohibit the building of any tower higher than the 50 meter (165 ft) high city hall, known as the Rognosa. Seventy two such towers were built, of which only 14 remain standing today.

The building of towers was very common in medieval towns and cities of the era, including in cities like Florence, Bologna and Perugia, but except for a few isolated instances, the towers either collapsed, were destroyed in war, or were pulled down during rebuilding programs.

They survived mostly because as peace came to the area, and people, towns and connecting highways moved to the valleys, San Gimignano lost the importance it had during the medieval era. In other words, the town retains its medieval appearance - and all that medieval charm - precisely because no significant changes have occurred within the city walls for hundreds of years.

But, because it has been so well preserved in its medieval condition, it is now a major attraction to tourists and travelers, whose money is now the economic life blood of San Gimignano. However, the fact that it is such a heavily touristed town should not deter you from visiting, although an off-season visit is recommended. It is a beautiful and unforgettable place, redolent of a profound, not a superficial, medieval atmosphere.

The color of its stone, a warm ochre, that radiates a golden lustre in the afternoon light, its twisted and winding streets, its convivial piazzas, its cool and solemn Duomo and churches, its charming cafes and restaurants, can take you back in time in a way that few other places can. And, from the tops of the famous towers, you can see a rolling, green and verdant Tuscany - a Tuscany you think only exists in your imagination, but is real indeed.

Jesse Andrews, 2016

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Beautiful Countryside in Chianti, Tuscany

Beautiful San Gimignano, Tuscany Italy

Streets in San Gimignano

San Gimignano Tuscany Escorted Tours

Map

Multi-Day Holidays Tours

Tuscany Mini-Stay

A brief retreat to Tuscany promises a delightful blend of Renaissance art, rolling vineyards, and charming medieval towns. This mini holiday in Tuscany provides a perfect taste of the region's art, culture, and culinary delights in just a few memorab...

Private

3 Days / 2 Nights

PRICING

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Florence, Tuscany and the Italian Riviera

A classic introduction to the must-see sites of Tuscany and Cinque Terre. From the wine-growing lands of Chianti and Val d'Orcia to the Renaissance splendour and the museums of Florence, the tour ends in the incredible natural beauty of the Italian...

Private

10 Days / 9 Nights

STARTING FROM

€5,450 per person

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Private & Small Group Tours in San Gimignano

Tuscan Wine Tour from Livorno

This tour is a perfect tour for foodies and wine lovers who want to get the most out of their time in Tuscany from the port of Livorno. Chianti is a large wine producing zone in the Tuscany region of Italy and is home to some of Italy's most notable...

Private

12 Hours

STARTING FROM

€200 per person

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Private Tour of Volterra and Her Incredible Landscapes including San Gimignano

Volterra occupies an incredible position overlooking an amazing, often unbelievable landscape in all directions. It is one of the highest towns in Tuscany and offers visitors a step back through time into Etruria and a look at the Etruscans, though i...

Private

PRICING

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Gourmet Tuscany: Truffle Hunting Followed by Cooking Class and Lunch

A wonderful morning of truffle hunting, cooking and wine tasting in the beautiful Tuscan countryside.

Semi-Private

4 Hours

STARTING FROM

€210 per person

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San Gimignano Morning Tour with Full Tuscan Lunch and Multiple Wine Tastings

North west of Siena, on the hills of Val d'Elsa, stands the medieval town of San Gimignano. Defined as the town "with a hundred towers", owing to the presence of these impressive buildings symbolising power and wealth, till the thirteenth century the...

Small Group

8 Hours

STARTING FROM

€60 per person

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Tuscany: Siena & San Gimignano from Florence or Livorno

This tour of Tuscany begins in either Livorno or Florence and includes a visit to two of Tuscany's most beautiful towns Siena and San Gimignano which are right in the heart of the beautiful Tuscan countryside inside the Chianti wine territory. Over t...

Private

8 Hours

STARTING FROM

€220 per person

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Pisa, Volterra, San Gimignano

This is one of our favorite private tours in the Tuscany region, exclusively offered by Italy Vacation Specialists. We can pick you up from your hotel in Florence, cruise ship in Livorno, or villa in Tuscany to begin this tour. During the tour, you w...

Private

8 Hours

STARTING FROM

€200 per person

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Hotels

Villas

Italy,Tuscany,San Gimignano

Villa

Villa for families between Florence and Siena

7 Beds 10-18

Air Conditioning +13 more

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Italy,Tuscany,San Gimignano

Villa

Villa near San Gimignano

5 Beds 10

Air Conditioning +14 more

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Apartment

Italy,Tuscany,San Gimignano

Estate

Apartment Virgo

1 Beds 1 Baths 3

Air Conditioning +7 more

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San Gimignano Tuscany Escorted Tours with Italy Vacation Specialists

Our Featured Properties

La Casa Fiorita featured rental property in San Gimignano Italy

Italy,Tuscany,Florence

Apartment

La Casa Fiorita

4 Beds 4 Baths 4/8

Air Conditioning +11 more

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La Masseria featured rental property in San Gimignano Italy

Italy,Tuscany,Arrezzo

Villa

La Masseria

2 Beds 2 Baths 4

Air Conditioning +11 more

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Italy,Tuscany,Siena

Villa

Villa in Siena for 8 People

4 Beds 8

Balcony +10 more

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Il Nascondiglio Verde featured rental property in San Gimignano Italy

Italy,Tuscany,Arrezzo

Villa

Il Nascondiglio Verde

2 Beds 2 Baths 4

Air Conditioning +11 more

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Italy,Tuscany,Florence,Montaione

Villa

Villa in Iano with breathtaking view

4 Beds 9

Air Conditioning +13 more

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Casa delle Brezze featured rental property in San Gimignano Italy

Italy,Tuscany,Florence

Apartment

Casa delle Brezze

2 Beds 2 Baths 4

Air Conditioning +12 more

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La Dimora Regale 1 featured rental property in San Gimignano Italy

Italy,Tuscany,Arrezzo

Villa

La Dimora Regale 1

1 Beds 1 Baths 2

Air Conditioning +11 more

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Italy,Tuscany,Lucca,Camaiore

Villa

Luxury villa near Lucca

8 Beds 16

Air Conditioning +12 more

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Cottage Riccio featured rental property in San Gimignano Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Riccio

Air Conditioning +7 more

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La locanda del gelsomino featured rental property in San Gimignano Italy

Italy,Tuscany,Cortona

Villa

La locanda del gelsomino

9 Beds 12/18

Air Conditioning +5 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa San Martino Cortona

3 Beds 5 Baths 12

BBQ +10 more

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La Dimora del Gazebo featured rental property in San Gimignano Italy

Italy,Tuscany,Siena

Apartment

La Dimora del Gazebo

3 Beds 2 Baths 6

Air Conditioning +16 more

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Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“I am a travel agent with All About Honeymoons and I would highly recommend Italy Vacation Specialists. Jessica was wonderful in helping us plan in a last minute anniversary vacation during high season without any issues. She even checked on our clients while on vacation to make sure things were going well. I plan on using them again soon ”

[Read More] Tammy Joyce, All About Honeymoons

“I have traveled to Italy 2x with the IVS for my own pleasure trips and 2x for business with IVS. These guys really pay attention and make your trip go like clockwork. Italy is nuts, just saying! There are so many rules and restrictions now, so we did not want to drive ourselves. Having traveled with them many times and done business on se”

[Read More] JoAnne Beaudoin, Retired Nurse

“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve high praise for the quality and efficiency of your work. BTW, Guiseppe was an absol”

[Read More] Jo Ann West

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and flying to Rome where honestly 4 days is NOT enough. They keep saying to spend more”

[Read More] Robin and Kumi Bruun, Tokyo Japan

“We're home now from the most amazing trip to Italy! I can't thank you enough for your efforts and coordination of what was without question the finest vacations I've been on to date.”

[Read More] Carol Carson

“As a travel agent, but also a traveler to Italy, thee is no other company I would recommend than the Italy Vacation Specialists. Not only do they really care about what they are doing, they also really know Italy and try to educate many people about ways they can best see the country and not fall into tourist traps. I have been on 4 trips”

[Read More] Laura Chomiak, Travel Agent

“Jesse & Giuseppe, Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.”

[Read More] Bob & Sandy

“This company really knows their stuff and recommended our family to stay longer in each location. We didn't listen to them, but wished we had in every single place we went. They recommended Sestri Levante over the Cinque Terre which was our favourite destination on our entire trip. We visited Rome where we stayed in the outstanding Hotel ”

[Read More] Sean & Veet Chapman, CGA

“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS team took a huge burden off of me! I would like to start of by saying "THANK YO”

[Read More] Ann Brownell, KHM Travel Group

“I traveled with JoAnn West through your services, guided by Giuseppe, in July of this year. What a wonderful experience; your service is really top notch! If I return to Italy for a tour, I will absolutely use your services again and recommend you to my friends!”

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