What to do and see in San Gimignano, Tuscany: The Best Historical & Heritage Tours

November 11, 2021 Misti Hsu

San Gimignano, known as the "city of beautiful towers," had 72 towers in its heyday. Now 14 remain, and, rising above Tuscany's Elsa Valley, they make the town look like a medieval dreamscape. Take in the fresco-covered Collegiate Church, the Civic Museum and the views from atop 177-foot Torre Grossa. Daytrippers from Florence tend to fill up the streets during the day, so for a more up-close-and-personal look at the town, spend the night.
Restaurants in San Gimignano

1. Explore Tuscany's Wonders in Three Nights and Four Days

Tuscan Safari
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5.0 based on 1 reviews

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this four Days and three Nights private excursion from Florence. Enjoy three different regional and world famous varieties: Nobile, Brunello, and Chianti Classico with a dedicated driver guide exploring the towns of Greve in Chianti and the square of Montalcino and Montepulciano, then pop into local wineries to learn about the local Sangiovese grapes and sip some Chianti, Brunello and Nobile. At your own discretion taste some Vernaccia wine in San Gimignano. Visit the historical cities and towns of Montalcino, Montepulciano, Greve in Chianti, San Gimignano, Florence, Siena, Pisa and Lucca. Visit the main squares and attractions, ticket to the Leaning Tower included in the price of the tour. There will be three wine tastings and round-trip private air-conditioned minivan transportation from your accomodation included.

Inclusions: Lunch, Air-conditioned vehicle, Bottled Water, Wine tastings, 3 Breakfast

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Reviewed By Lisa M

The day was good however a couple of constructive feedback points for you 1) when I first looked at the trip the meeting point was at the end of the road the hotel was on, however your e-ticket and website made us go to the main bus station 20 mins tram ride away and the tour guide commented as I hadn’t checked in a Julian’s Bar, as everyone else had. 2) the second point is to do with the final leg of the trip in Siena, when it was pouring with rain and we were about to head back to the bus and the tour guides boss had come up with another great idea for the small cost of €3 everyone could get the trenino back to the bus, half the clients didn’t want to do this and we were made to stand in the rain getting wet whilst the main tour guide waited for the trenino to arrive before the walkers were allowed to set off on foot back to the bus. Had I not stepped up and asked for the walkers to be allowed to walk with a guide without waiting, we would of been soaked!

2. Private Day Trip from Rome to Siena and San Gimignano

Rome First Choice Tours
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5.0 based on 1 reviews

Discover The Beauty Of Siena And San Gimignano, Traveling Through The Countryside Of The Chianti Region, With Ever Changing Scenery Of Vineyards And Olive Trees On This Full Day Private Trip From Rome. Since It Is A Private Tour So The Itinerary Is Flexible And You Can Change It As You Want , Your Driver Will Always Give You The Right Suggestions According To Your Preference

Inclusions: Transportations, Expert Driver/Guide, Pickup-Drop-off / From-To Hotel, Fuel surcharge, Parking Fees

Exclusions: Attraction Tickets if any, Gratuities , Wine tasting and lunch ( cost is 30 Eur per person to be paid at the winery )

Reviewed By Abdelmoneim

Assem is the best tour guide ever. The tour was so informative, funny and exclusive. You live the history and know small details that make you value the Colosseum. Don't forget to take photos everywhere.

3. San Gimignano Walking Tour and Vernaccia Wine Tasting - Private tour

San Gimignano Porta San Giovanni, 53037 San Gimignano, Province of Siena, Italy Book Tuscany Experiences
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5.0 based on 2 reviews

Explore the historical town of San Gimignano UNESCO World Heritage Site, known by many as “The Manhattan of Tuscany” due to its unique features handed down through the centuries. Taste the famous local white wine “Vernaccia” relaxing in a panoramic terrace, with an amazing view on the Tuscan rolling hills. Join this guided tour for small group led by a funny local guide to discover the best of Tuscany!

Inclusions: Professional guide, Vernaccia tasting

Exclusions: Private transportation, Lunch, Torre Grossa entrance ticket

Reviewed By Mozzie54

A Thunderstorm met us as we left the train station at Lucca to meet our guide, Davide. Thankfully it did not last too long and we were able to enjoy the passion for Lucca that Davide shared with us as we strolled around the walled township. We couldn't help feeling like we wanted our tour to continue as David filled our imaginations with his story telling and making the city come alive for us.

4. Small group Day Tour of Siena and San Gimignano from Florence! Tuscan Beauty!

Piazza di San Firenze, Piazza di S. Firenze, 50122 Firenze FI, Italy Viaggi d'Ambra
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5.0 based on 5 reviews

This is a wonderful way to explore two of the most scenic medieval towns in Italy. On board of a comfortable van you will experience the easiest way to visit those iconic towns of Tuscany in one day without stress, door to door service. The meeting point is in Florence centre, very easy to find.

Inclusions: Air-conditioned vehicle, Private transportation, The professional english speaking driver will explain you the attractions and traditions of towns

Exclusions: Lunch, Gratuities, Professional licensed guide (available on request with extra cost)

Reviewed By flobo5

My family and I first came into contact with Viaggi d'Ambra in July when I contacted them about a Chianti tour (see previous review) - we loved it so much, we didn't only book once again, but twice! My husband and I had the pleasure of a tour with Azzurra in the Montepulciano and Montalico regions in August - it was amazing! Both wineries were in lovely positions and the hosts were delightful. We also had time to explore the beautiful town of Pienza - not to be missed! After two fabulous tours, we booked to return to Tuscany in October. This time Christian took us on an amazing tour of northern Chianti. We visited the beautiful town of Greve and two fabulous wineries. Without Christian, we would never have found them and their wonderful wines! This year has all been a bit mad, but do book early for tours next year as Azzurra and Christian are fantastic people and know the area like no other. If you don't book, I can see myself taking tours with them daily - it really is such a fantastic experience and such a varied area! Grazie mille both of you!!!

5. Tuscany Experience in Pisa, Siena, San Gimignano & Chianti

Sightseeing Experience Visitor Center (tourist assistant), Stazione, atrio biglietterie, Piazza della Stazione, n.1, 50123 Firenze FI, Italy Sightseeing Experience
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5.0 based on 1 reviews

Your day starts in the morning with a free tour of Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous Leaning tower of Pisa. Afterwards, we'll move in a Typical Winery in the Chianti Hills, on the slopes of San Gimignano, where we will enjoy a typical Tuscan lunch with a good local wine tasting. After lunch you discover, San Gimignano: the Medieval Mahanattan, where you can explore the maze of cobbled streets, small squares and many local craft stores. Our exciting day continues with a panoramic view of the true Chianti countryside before arriving in Siena, where our professional guide will let you discover the most important squares, from Piazza del Campo to the Cathedral passing through the most beautiful ‘Contrade’ that characterize this city. At the end of the guided tour, you will have free time to enjoy a cup of coffee or the Pan Forte (the typical local cake) and have some shopping in typical local shops.

Inclusions: Transfer with equipped GT bus with conditioned air , Expert multilingual excort ( not for Private Transfer Only ) , Free time in Pisa and San Gimignano , Guided Tour in Siena ( not for Low Cost, Private Transfer Only and Private & Lunch ) + Free Time , Lunch in a typical winery in the Chianti area ( not for Private Transfer Only ), Tasting of 3 Wines and Olive Oil ( not for Private Transfer Only ) , Cantuccini tasting (typical Tuscan biscuits) ( not for Private Transfer Only ) , Wi-Fi on board the bus

Exclusions: Pick up service ( For Private Tour, you can ask for it, if the hotel is in city centre )

Reviewed By RobbieFPB

Wish we had read the reviews before booking. Palermo is quite small and most the main sights are very central, so you don’t really need a bus tour. However, even if you are not keen on walking, the bus tour will be of little use, as the advertised ‘hop on, hop off, every 20 minutes’ is simply untrue. The bus only arrives every 90 minutes (we lunched in a restaurant next to the stop we alighted from and that was the time gap). In addition, there is no access to a live map for bus arrivals, so you have no idea when the next bus will arrive. In a nutshell, it’s a rip off.

6. PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

UniqueTuscany private Tours
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5.0 based on 27 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • With this fascinating tour you will discover a unique part of Tuscany in a private day-trip from Florence. With an expert local driver/guide, immerse yourself in the renowned Chianti wine region and explore the cities of Siena and San Gimignano. You will tour historic landmarks such as Piazza del Campo in Siena, home to the annual Palio, and the medieval towers of San Gimignano. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the wine cellars by your guide • Taste Craft Chianti Classico wine at a local vineyard • Pick-up and drop-off at your Hotel or at the address provided • Travel in a Mercedes-Benz minivan

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes-Benz MiniVan, Air-Conditioned, English-speaking licensed driver, Free time in Siena and San Gimignano, Unlimited cold mineral water , On-Board WiFi

Exclusions: Local guides in Siena and San Gimignano, Lunch in farm or winery available at an extra cost 25€pp to 50€pp, depending on option chosen, Entrance fees (Cathedral of Siena ia approx. 7€ pp.)

Reviewed By Gabriel S

This was our 2nd private tour that we did through Uniquetuscany (2017/2020). Our guide, Alessandro was very specific to the covid restrictions and offered us new masks during the day! He did a wonderful job explaining the history of the towns. Our highlight was the visit to Tuscany organic farm where we had our lunch with amazing view. We stopped at Siena, San Gimignano and Pisa. There was a lot of walking and moving from in and out of the minivan so make sure you wear comfortable shoes. I definitely recommend this tour while visiting Florence since you get a lot of history while on the minivan to each town. Just not enough time in all the towns but 10 hours is a long day! still worth the trip! Highly recommended..

7. Small Group Tour: Tuscany Wine Tour Siena and San Gimignano - Full Day Tour from Rome - Tasting and lunch included

Welcome Italy - Day Tours
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4.9 based on 27 reviews

Enjoy travelling through Italy on a full-day journey from Rome in a Small Group max 12 people (only 6/7 per minivan), we'll through the hills of Chianti to visit the cities of San Gimignano and Siena. Explore the UNESCO-listed historic town of San Gimignano with its many Medieval towers. Stop for a wine tasting in the Chianti region, where you'll sample 10 types of wine and oil, and have lunch on the estate. Visit charming Siena, known worldwide for the famous Palio horse race.

Inclusions: Free transfer offered by Welcome Italy in air conditioning Minivan, Tour-guide escort, Wine tasting, taste local products and lunch, Hotel pickup and drop-off (central Rome only), Emergency number also operational via whatsapp

Exclusions: Gratuities, Tips

Reviewed By pilotjdk

had small group vacation planned for last October. cancelled due to Covid. Was offered voucher or refund. told them we needed refund due to not knowing if we would be travelling within a year. was told they would refund our money. Still waiting on a refund of 2084 and 1500 Euros.. that was over 7 months ago when it was cancelled. numerous emails. most of the time no response. Was promised refund when the person handling our group returned to work. nothing yet... Was really looking forward to a great vacation.

8. Full Day Experience: San Gimignano & Siena Guided Tour from Florence

Piazza dell'Unità Italiana, 50123 Firenze FI, Italy City Wonders
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4.8 based on 9 reviews

Spend a day touring the idyllic countryside of Chianti, Tuscany by private coach, stopping to explore the UNESCO World Heritage towns of Siena and San Gimignano. Cutting down on waiting with Skip-the-Line Access at the busiest sites, you’ll have time for guided tours, time to yourself, and even a sample of local wine.

Inclusions: Expert, English-speaking tour leader throught the day , 1 hour guided tour in Siena with local guide, Tasting of local wine, Round trip transportation on air conditioned comfortable bus, Headsets when appropriate, so you can always hear your guide

Exclusions: Hotel pick-up and drop-off, Food/Beverage, Gratuities

Reviewed By carloseqg

This tour was so so good. Our tour guide Angelo was amazing. He knew everything there was to know and was able to answer any and all questions brought up to him even if they were about things not related to the tour exhibitions. It was worth seeing both the Uffizi and the Accademia. There were no lines to skip due to the covid-19 situation as we took this tour a week before things got shut down but I would recommend this tour to anyone coming to florence as it is not only a tour of the two big galleries but also a small city walking tour.

9. Private Excursion to Siena, San Gimignano and Chianti Landscapes

Caf Tour & Travel
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4.8 based on 22 reviews

Discover the beauty of Siena and San Gimignano, traveling through the countryside of the Chianti region, with ever changing scenery of vineyards and olive trees on this full day private trip from Florence.

Inclusions: Pick up and drop off at your Hotel if centrally located in Florence, Transport by deluxe air-conditioned vehicle with WIFI on board, English/Italian speaking driver, Local professional Guide at your side in Siena

Exclusions: Gratuities, Guide Service in San Gimignano, Entrance fees to the Cathedral in Siena, Everything not mentioned as Included

Reviewed By aakebe

Only 7 people and the tour was by Van. The driver guided us during the drive but no guide joined us at our stop in Castellina. Professional presentations at the wineries. Especially at Poggio Amorreli with Andrea where we were treated with Spumante, one white and two red Chianti and one supertuscan. We also got bread, cheese, salami with their own balsamic vinegar and olive oil. The driver called for a taxi upon arrival in Florence ????

10. Small Group Tour to San Gimignano Siena and Chianti from Pisa

McDonald's Pisa Miracoli, P.za Daniele Manin, 1, 56122 Pisa PI, Italy My Tour in Italy
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4.6 based on 19 reviews

Enjoy a full-day tour into the heart of the beautiful Tuscan countryside; visit the town of San Gimignano, the wine territory of Chianti, the medieval town of Siena and the Monteriggioni fortress.

Inclusions: Travel by GT coach or minivan, Expert multilingual escorts, Lunch consisting of typical Tuscan dishes, Visit of a famous wine estate, Wine tasting

Exclusions: Gratuities, Pickup and drop-off

Reviewed By Oversunsetplain

I couldn’t put correct date on this review - I did this tour with my two children in August 2019 and originally posted it then. I have had a message to say that I had posted it under the wrong company (one with a very similar name). I would like to re-post the review as we had such a brilliant day with our guide and would like to recommend the tour company to others whenever this type of activity goes ahead again! Our guide Ms Ivanova was very knowledgeable and friendly. The tour took in many places around the city and we also visited the Uffizi in the afternoon. I was with my children aged 6 and 9 and both really enjoyed this day. They felt included and learned a lot. The guide met us at the times planned and gave plenty of opportunities for questions and were able to answer any queries. Everything was organised well and went smoothly. We were unable to book a tour inside the Duomo but actually this one which took us all the way around the outside and to other fascinating parts of the city was perfect for my family.

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