Things to do in Castellina In Chianti, Tuscany: The Best Private Tours

November 2, 2021 Misti Hsu

An ancient town of just under 3,000 between Florence and Siena, picture-perfect Castellina In Chianti is set in the wine-famous Chianti Hills. The many wonderful sights include the imposing 14th-century Rocca (Fortress), offering spectacular views of the town and surrounding countryside, the 16th-century San Salvatore church and the Via delle Volte medieval arched passageway. Just outside of town are the pre-Roman Etruscan burial tombs of Monte Calvario and the Necropolis of Poggino.
Restaurants in Castellina In Chianti

1. Chianti Vineyards Tours in Private Luxury Van from Florence

Chianti Drivers
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5.0 based on 10 reviews

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent wines.  • Visit small villages such as Greve, Castellina and Radda in Chianti and ancient castles, hidden among green hills and surrounded by vineyards and olive groves. • This tour is a perfect combination of culinary delights, arts and culture. This private tour can be customized from locations you visit to the starting time of the tour.

Inclusions: Hotel pick up and drop off, Private luxury minivanand a expert English speaking driver, Fresh bottled water, Free Wi-Fi on board (on request at reservation), French, Spanish or Portuguese speaking driver upon request

Exclusions: Lunch (from 25€ to 50€ per person), Wine tastings (from 10€ to 25€ per person), Gratuities

Reviewed By kwoodrum6

Truly an amazing experience! This private tour was the highlight of our trip to Italy and perhaps the best holiday experience we’ve had so far in our lives. Simone was so welcoming and flexible with the schedule. He gave great backgrounds to the places we arrived at, with personal connections. The winery we stopped at was truly magical; we had a wonderful private lunch, with a tour around the vineyard and wine tastings. This was the best vineyard experience we’ve had so far and was such a ray of sunshine on our day. The personalized experience was beyond anything we could have arranged on our own. Highly recommend!

2. 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 ????

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. Private The Essence of Tuscany: Chianti Classico, Montalcino, Montepulciano

Caf Tour & Travel
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5.0 based on 1 reviews

Following the scent of the Great Wines through the most stunning landscapes of Chianti, Val d’Orcia and Val di Chiana

Inclusions: Pick Up and Drop Off at the hotel in Florence if centrally located, Transport by deluxe ari-conditioned vehicle with WIFI on board, English/Italian speaking driver, Typical Tuscan Lunch in a family run Farm, Wine and Food Tasting with 3 wines and local products in a cozy Winery

Exclusions: Gratuities, 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 ????

5. Siena, San Gimignano & the Chiantiside private tour with Mercedes V class Van

Bespoke Italian Tours
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5.0 based on 3 reviews

Our tour is made with passion by expert english speaking drivers who know everything about the area. We will start with Siena, a Medieval & Reinassance gem, famous for its stunning sights and impressive buildings. We will stop by the best places to take pictures, dropping you off in front of the amazing cathedral (the highest point of the city). From there you'll take a delightful stroll down to the Piazza del Campo, the main square with its beautiful bell tower, than walk up to the Salimbeni square, headquarter of the oldest still operating bank in the world. From there we will meet again and drive to a beautiful farm in the hills, to have the best lunch with local wines. After that we will take a scenic drive to San Gimignano, the Manhattan of Tuscany, famous for the house towers, the white Vernaccia wine, the golden saffron and the best Gelato in the world. From there we will take a relaxing drive back to your place, making extra stops if we finished early!

Inclusions: WiFi on board, Air-conditioned vehicle, Private transportation, Bottled water, Fuel surcharge, Parking Fees

Exclusions: Lunch in family run winery is 50€ per person with wine tasting

Reviewed By F5679VVchriss

Amazing experience. Niccolo picked us up at our villa and took us on a wonderful tour of Tuscany and two excellent wineries, with one of them also hosting us for lunch. He is an articulate guide and provided multiple recommendations to enhance the remainder of our family trip. I would recommend Niccolo and his company without hesitation to anyone looking for a great time in Tuscany. Thanks Niccolo.

6. Grape stomping in Tuscan farmhouse from Siena

Basilica Cateriniana San Domenico, Piazza San Domenico, 1, 53100 Siena SI, Italy Tuscany Private Tour
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5.0 based on 1 reviews

Stomp on grapes in a small winery in the beautiful Chianti hills. Experience the feeling of grapes under your feet and discover the secrets of winemaking during your 4-hour tour with English-speaking guide. Enjoy a homemade lunch with a wine-tasting session at a 200 year old villa. Visit its ancient wine cellar. (From late August to mid September, grape picking is also involved on request).

Inclusions: Professional guide, Local guide, Wine-tasting, Lunch

Exclusions: Gratuities

Reviewed By 628brendah

What an amazing day! It started with truffle hunting with Roberto and his two dogs - Ori and Chloe! We learned a lot about truffle hunting and how the dogs are trained. Chloe was 'in training' and it was fun to see how Roberto used both dogs. They found about 12 truffles in all of various sizes! Then we headed to a small family winery where we ate the fruits of our labor!!! We had a 4 course 'absolutely delicious' meal, tasted a lot of great wines, in addition to olive oil and honey! We even bought a bottle of wine to take with us and watched Sylvia add the DOCG label by hand (which are closely tracked by the region)! We had a great tour guide, Paelo, with us the entire day! He picked us us at our farmhouse, was our translator when needed, was very courteous and informative! I would highly recommend this very unique experience! And I would recommend Tuscany Private Tours. They were very easy to communicate with and very responsive!

7. 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.

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 Full-Day Siena and Chianti Classico Wine Experience.

UniqueTuscany private Tours
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5.0 based on 6 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • Leave behind the bustling city of Florence with a private full-day tour in a luxury Mercedes Minivan. Stroll through the Gothic streets of Siena and discover the black-and-white art and architecture of its historic center, a UNESCO heritage site. Taste renowned Chianti wines and authentic Tuscan cuisine in famous family-owned cellars of local olive oil and aged balsamic vinegar. • 8hr Full-Day private tour of Siena and Chianti from Florence • Pick-up and drop off at your selected hotel/ location (Florence Down Town) • Private transportation by Mercedes Minivan, Air-Conditioned • Tasting of cold cuts and cheeses from the exceptional Falorni butcher shop • English-speaking licensed driver • Learn about local history, food and culture • On request we can organize Lunch in Farm or Winery. (highly recommended)

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes Minivan air-conditioned , Unlimited cold mineral water , Tasting of cold cuts and cheeses from Falorni butcher, Local guide tour in winery, On-Board WiFi

Exclusions: Lunch and wine tasting on farm or winery (to be paid on-location from 25€pp to 45€pp), Wine tasting (to be paid on-location from 0€pp to 25€pp), Private city guide.

Reviewed By Journey40774728396

We booked with Alessandro for a day trip from Florence to Siena and San gimignano as we were in Italy for my wife's business, so we decided to visit Tuscany for the third time. COVID wasn't a big deal yet, but the cities were practically deserted.. Alessandro was a delightful tour guide and host. (great with communications, reasonable price and very comfortable car and driver) Alessandro is extremely friendly, and it was a pleasure to meet him and have accompanied him around for the day. I don't know how he did it but every time we were leaving from anywhere, without even having to text him or look for him, he was there waiting for us with the door open! We were able to spend a really relaxing and enjoyable day touring the vineyards thanks to Alessandro so organized and professional! We love Florence!!!

10. Private Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Chianti Drivers
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4.9 based on 48 reviews

*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8/9-hour tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * With agreements during the reservation we can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lover.

Inclusions: Hotel pickup and drop-off in Florence, Private luxury minivan, Bottled water, Onboard Wi-Fi (on request at reservation), Our drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs., Spanish-, Portuguese- or French-speaking driver upon request

Exclusions: Lunch in winery or farm. (to decide at the time of briefing in the morning with your driver), Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

Reviewed By Laurettab1974

We had a fab day! Our driver, Massimo was great! Very engaging, informative and made so enjoyable trip. Satisfied and exceeded our expectations Not only the tour through Tuscany was beautiful and the wine delicious, but above all Max made the whole experience unique! I recommend ChiantiDrivers to anyone! I highly recommend it.

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