Things to do in Province of Siena, Tuscany: The Best Sightseeing Tours

November 4, 2021 Misti Hsu

The Province of Siena (Italian: Provincia di Siena) is a province in the Tuscany region of Italy. Its capital is the city of Siena.
Restaurants in Province of Siena

1. Chianti Dreaming: Private Boutique Winery and Hilltop Village Tour

Caf Tour & Travel
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5.0 based on 2 reviews

Have a slow and fascinating Chianti Experience! Discover in total comfort all the charm of the most beautiful countryside in the world and experience its culture, history and traditions, walking along the ancient streets of a picturesque Medieval village. Savor the best local flavors through a scrumptious wine tasting in an enchanting winery, surrounded by a breathtaking scenery!

Inclusions: Pick-up and drop-off at the hotel in Florence if centrally located, Transport by deluxe air-conditioned vehicle with WIFI on board, English/Italian speaking driver, Delicious tasting of three excellent wines and typical products, in a small-scale production winery., Stop in Greve in Chianti and in a second winery (wine tasting with 4 wines) if option selected

Exclusions: Gratuities, Guide Service, 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 ????

2. Private Wine and Extra Virgin Olive Oil Tasting

Via Martiri di Citerna, 53037 San Gimignano SI, Italy Podere La Marronaia- Sosta Alle Colonne
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5.0 based on 1 reviews

Take a break in a family farm surrounded by the flavors of the Tuscan products. Dive into the green shades of our vineyard and olive groves with a private and exclusive tour together with a family member. Enjoy a full wine tasting and olive oil tasting in a rustic house that overlooks the green Tuscan hills. All our organic wines and olive oils come straight from the winery’s own vineyards and olive trees. We are just a few minutes’ walk from San Gimignano town center, with a stunning view on the Tuscan countryside and the Medieval towers of the town. An Italian or English-speaking member of the family will guide you in the experience with a professional and family warm welcome.

Inclusions: Bottled water

Exclusions: Lunch

Reviewed By gtravelbug15

We had the best day of our vacation, at the Marronaia winery. The hospitality of all the staff made us feel welcome and like family. Learning to make authentic pizza and Prosecco gelato was a memory to take home with us. Wine tasting and olive oil tasting has committed us to staying in touch with the family and winery. I now order their wines regularly that get shipped to the states with absolutely no glitches. My all time favorite is the Sparkling Rose' called Quarzo. Whenever I share it with friends, they want more of it. I'm a little embarrassed to say how many cases I've ordered in a short amount of time. It really is that good!! We also love their olive oil. The fond memories of our day at the winery is calling us back to revisit the experience. Thank you to the family that cares to make their guests experience memorable, leaving with fondness in their hearts to return.

3. VESPA Tour in Tuscany

Tuscany Private Tour, Via, Viale IV Novembre, 35, 53011 Castellina in Chianti SI, Italy Tuscany Private Tour
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5.0 based on 4 reviews

Nothing speaks ‘romanticism’ more than a tour on a Vespa, a ride through history and style, that can really change the tone of your holiday. The Vespa experience offers an original take on touring Tuscany, while we take care of each and every detail. Leave chaos behind you, enjoy the best of Tuscany’s landscapes from your Italian Vespa and skip traffic like Italians do. Discover the beautiful Tuscan hills riding a Vespa scooter. Visit three quaint villages during your 6-hour tour with English-speaking guide. Enjoy a homemade lunch with a wine-tasting session in our organic farm. Visit its ancient wine cellar.

Inclusions: Lunch, Wine tasting, All activities, Tour escort/host, Hotel pickup and drop-off (selected hotels only), Use of helmet, Private tour, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By S B

This was a magical experience, we will remember it forever! My girlfriend and I were staying in Castiglione della Pescaia and didn't have a car, so at Tuscany Private Tour they tailored the whole program to our needs. They sent Filippo to pick us up from right below our airbnb, and he took us to different vineyards and borghi in the area and told us about the history of these places. He was extremely professional but also very friendly and receptive to our needs. He told us he also organises tours of Tuscany by bike and this is something we will definitely consider doing with him in the future. We would highly recommend him and the agency if you want to experience something special that you won't forget.

4. Orvieto and Montepulciano Wine Tasting Private Day Tour from Rome

Rome Italy Explora
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5.0 based on 1 reviews

Want to visit Italy, but looking to see more than just the tourist cities? Orvieto is your answer and is perfect for a day trip from Rome. The historic, and beautiful section of the city is located at the top of a steep hill. The well-preserved Gothic and medieval buildings will make you feel like you're frozen in time. You can easily walk out of beautiful architecture, historic buildings, or interesting spots to people-watch. Montepulciano, Montepulciano, Montepulciano, Montepulciano, Montepulciano, Montepulciano in Italy and abroad. Montepulciano has a distinct peculiarity, in which you have been dug out underneath the prestigious palazzos.

Inclusions: Pick-up and drop off with luxury transportation and private chauffeur, Private English-speaking tour escort at your disposal, Entrance tickets in the Orvieto Cathedral (Duomo), Light wine tasting in Orvieto, Visit to the most ancient and beautiful wine cellar in Montepulciano, Wine tasting with three different wines in Montepulciano, Snack with local products (cheese, cold cuts) in Montepulciano

Exclusions: Food or drink choices made outside the scope of the organized tasting tour, Gratuities (optional)

Reviewed By GiulianaD137

We wished we could see Pope Francis but we could never expected we could see him so closely thanks to Rossana great effort. Rossana and our driver Luigi are both great persons and the visit to the Pope very well organized. They both were professional, supportive, engaging and very helpful. Rossana took really a great effort to make the visit tailored to our needs and she had great sense of humour. Big thanks to R and L. We would highly recommend this tour.

5. Montepulciano from above!

Porta al Prato, Via Gracciano nel corso, 53045 Montepulciano SI, Italy Elisona Lishi
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5.0 based on 1 reviews

That's a walking tour in the center of Montepulciano. We are going to visit the main attractive, the narrow streets, the panoramic views of the town, then we will go up in the Tower Hall, the highest point of Montepulciano to have a breathtaking view of the Valleys around the city. Then we will finish the tour with a Wine tasting.

Inclusions: We are going to an ancient Wine Cellar so you can taste the Vino Nobile di Montepulciano.

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6. Truffle Hunting with Wine Tasting in Tuscan farmhouse

Tuscany Private Tour, Via, Viale IV Novembre, 35, 53011 Castellina in Chianti SI, Italy Tuscany Private Tour
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5.0 based on 2 reviews

An amazing daytrip in the countryside to enjoy the gems of Chianti area production: truffle, wine and extra virgin olive oil, all in and around the same traditional family farm. Follow the expert truffle man and his trained dog in the forest to witness with your eyes how it is possible to find underground these edible treasures and the strong bond between trees and truffles. Back in the farm, you will have a wonderful lunch based on the truffle you found in the woods. Extra virgin olive oil and traditional Chianti Classico wine will accompany your lunch with a guide that will explain all the procedure of oil and wine production, showing all the phases of the work. Spend a day in a hidden place in the Tuscan country away from the city, with both the emotion of the hunting and the relax of the home-made lunch you will enjoy surrounded by the sounds of nature. For sure a memory will last forever.

Inclusions: Transport by air-conditioned minivan, Tour escort and Driver/guide, All activities, 3-course lunch, Wine tasting, Extra virgin olive oil tasting, Honey tasting, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By SRif914

We took a private tour of two incredible vineyards in Montalcino while on our honeymoon. Gaia was our tour guide and was absolutely incredible! Her knowledge of the wine industry and outgoing personality made this one of the best experiences of the trip. We will absolutely be recommending this tour to our friends and are excited to come back and explore more of Tuscany with Tuscany Private Tours.

7. Civita di Bagnoregio + Orvieto + WineTaste in Montepulciano Private Tour from Rome

Rome Italy Explora
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5.0 based on 1 reviews

Want to visit Italy, but looking to see more than just the tourist cities? Orvieto is your answer and is perfect for a day trip from Rome. The well-preserved Gothic and medieval buildings will make you feel like you're frozen in time. Together with Montalcino, Montepulciano is well known for the great production of red wine, it "Noble of Montepulciano" is one of the most appreciated Italian wines in Italy and abroad. Civita di Bagnoregio is a magical, surreal, fantastic place located on a top of a hill that can only be reached by crossing a narrow pedestrian bridge. Nick-named "the town that is dying", two citadel has Etruscan and Medieval origins. Suspended in time and space, Civita di Bagnoregio is beyond doubt one of the most beautiful and characteristic Italian villages. Arm yourself with a camera because you will be faced with breath-taking views!

Inclusions: Pick-up and drop off with luxury transportation and private chauffeur, Private English-speaking tour escort at your disposal, Entrance tickets in the Orvieto Cathedral (Duomo), Light wine tasting in Orvieto, Visit to one of the most beautiful wine cellars in Montepulciano, Wine tasting with three different wines in Montepulciano, Snack with local products (cheese, cold cuts) in Montepulciano, Entrance tickets to Civita di Bagnoregio, Free time in Bagnoregio

Exclusions: Gratuities (optional), Food or drink choices made outside the scope of the organized tasting tour

Reviewed By GiulianaD137

We wished we could see Pope Francis but we could never expected we could see him so closely thanks to Rossana great effort. Rossana and our driver Luigi are both great persons and the visit to the Pope very well organized. They both were professional, supportive, engaging and very helpful. Rossana took really a great effort to make the visit tailored to our needs and she had great sense of humour. Big thanks to R and L. We would highly recommend this tour.

8. 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..

9. Private Tour: Secret Siena Walking Tour

Piazza del Campo, Il Campo, 53100 Siena SI, Italy Tuscan Escapes
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5.0 based on 20 reviews

Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter side of Siena.

Inclusions: Local guide, Private tour

Exclusions: Gratuities, Transportation to/from attractions

Reviewed By Paul D

We could tell within the first minute that our guide, Georgia, was going to give us a fantastic tour of Siena and we wern’t disappointed. Georgia brought the history of Siena to life with interesting stories, a sense of humour and an incredible depth of knowledge.

10. Private Chianti Wine Tour with Lunch, a Visit of San Gimignano, Organic Wineries

Via Curtatone, 9, 50123 Firenze FI, Italy Chianti Wine Tour by Fun In Tuscany
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4.9 based on 276 reviews

Private Tour. First we tour vineyards and cellar of an organic farm in the heart of the Chianti region, receiving an up close look at the production and ageing process of the Chianti wines and learning about the secrets of the extra virgin olive oil making. This experience includes a  wine tasting and the opportunity to buy for cheap the best tuscan wines. Our trip continues on to the  medieval town of San Gimignano, where you will also have the chance to try the famous world champion Dondoli gelato. We then move on to a second winery where we enjoy an authentic  tuscan lunch, combined to a wine tasting class. A fine selection of Tuscan wines are presented by a wine expert to be paired with antipasti toscani, ribollita soup, lasagna with truffle olive oil and more.. On our way back we stop at  Piazzale Michelangelo, in the top ten of the most romantic spots in Europe.

Inclusions: Transport by air-conditioned confortable minivan, Lunch, Wine tastings, A visit of two wineries, Private wine tour, Live commentary on board, A visit of San Gimignano, A visit of Michelangelo Square

Exclusions: Hotel pickup and drop-off

Reviewed By KFDOCTOR

Your trip to Tuscany is incomplete if you do not go on this tour !! Amazing selection of Wines and Cheese. You are served some great food and the scenery is out of the world. Do not miss San gimignano you will get to taste the world's best gelato !!

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