Siena
Castle & Palace Tours

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Our most recommended Siena Castle & Palace Tours

Florence: Experience Siena, San Gimignano, and Chianti

1. Florence: Experience Siena, San Gimignano, and Chianti

Explore the beauty of Tuscany in this tour from Florence to Siena, Castello di Monteriggioni, Chianti, and San Gimignano. Visit medieval towns and villages, and drive through idyllic vineyards, with the option to stop at an organic farm and winery for lunch. Meet your friendly guide at your accommodation and drive in an air-conditioned minivan to see the distinguished medieval architecture in Siena, like the seashell-shaped Piazza del Campo and Siena Cathedral before enjoying a scenic drive to Castello di Monteriggioni. Enjoy the small, fortified village and take a short stroll after lunch at one of the local restaurants. Travel along the Chianti wine road which is rich with castles and villages with a stop to admire a small medieval village surrounded by endless vineyards. Experience a unique dining setting while taking in an amazing Tuscan panorama with lunch at an organic farm in Castellina, with the lunch option. Journey to historic center of the picturesque medieval town of San Gimignano and see its ancient towers.

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Medieval Castles & Chianti Wine Tasting Tour with Lunch

2. Medieval Castles & Chianti Wine Tasting Tour with Lunch

The first stop on your full-day tour of Chianti will be at the walls of Castello di Brolio, where you’ll get an up-close look at the picturesque vineyards. It was here that Baron Bettino Ricasoli introduced the world to Chianti red wines, known around the world for their distinctive taste and easy drinkability, and for the straw flasks, which at one time covered the bottles. Next stop on the tour is Castle of Brolio as well as the hilltop town of Radda in Chianti. While visiting the castle and its grounds, you’ll learn about its origins and history, and then enjoy a tasting of it's wine. Enjoy lunch here, it will consist of local, traditional Tuscan specialties.  In the afternoon it will be time to visit to a third winery. Meet the local producer and tour the estate that has been in the hands of the same family for many centuries. Visit the old cellars and learn about the traditions of the Chianti folk, while savoring and learning about great Chianti wines. The estate’s wines are made from Merlot, Sangiovese, Cabernet Sauvignon, Chardonnay, and Pinot Bianco grapes. You’ll sample 4 different wines, including 1 white wine, 2 red wines, and a special dessert wine, all of which are in limited production and only available at the villa.

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Siena: Half-day Guided Hike to Monteriggioni

3. Siena: Half-day Guided Hike to Monteriggioni

Give your mind a rest from the noise of the crowded towns, follow your expert guide on a pleasant walk along the Via Francigena, an ancient pilgrim route for the first time plotted down by the Arcbishop ‘Sigeric the serious’ of Cantebury on his return from Rome in the 9th century and considered the main artery to Rome throughout the middle ages. This route, that has for centuries been a highway of men and emotions, a spiritual pilgrimage and a wealthy trade route, has been forgotten and almost entirely relegated to history by the modern paved car roads. Only recently the route has been brought back from the grip of modernity and is today enjoyed by many pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in it's wonderfully preserved castles, villages and ruins.  See the Tuscany you would never want to miss before returning home, pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni. A medieval walled town located on a natural hillock, built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence.  Once in Monteriggioni, enjoy a guided tasting of local organic wines before saying goodbye to your guide for the end of the tour. Feel free to explore the village and the surrounding area at your own pace. You will be given a bus ticket to return to Siena.

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Antinori Winery & Brolio's Castle: Private Tour

4. Antinori Winery & Brolio's Castle: Private Tour

Start your day at the office of the local partner, perfectly positioned in the city center. You will meet your personal driver with an exclusive car and your local private guide as well as wine expert. Leaving the city center, the first stop of your visit to Chianti will be Antinori's cellar in Bargino, a wonderfully innovative winery located in the green Chianti hills. Inside the cellar you can taste different types of wine, listening to stories and anecdotes about the Antinori family told by the guide who will accompany you on this wonderful journey. After this visit, you will have lunch in a typical Tuscan restaurant "La Cantinetta di Rignana", halfway between the Antinori vineyard and Brolio's Castle. Here you can taste local salami, cheeses, Tuscan crostini, extra virgin olive oil, pasta or meat dishes, accompanied by wines and local products. Ending the lunch, you can enjoy some free time inside the restaurant, which is also a farmhouse. The last stop of the visit will be the Castle of Brolio and the Barone Ricasoli vineyard. Here, you will privately visit the castle and the vineyard, discovering the cellars and the finest quality wines, tasting most of the local production, tasting every single glass, accompanied by the guide's explanation. When you're ready, you will return to Florence in your exclusive car.

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Chianti: Private Tour & Wine Tasting at Castle-Wineries

5. Chianti: Private Tour & Wine Tasting at Castle-Wineries

Explore three of the most ancient and emblematic castles in the heart of Chianti Classico, which also serve as wineries. Visit beautiful estates erected centuries ago and taste a wide variety of prestigious wines. Feast on a gourmet lunch fit for a king as part of this tasting adventure. Enjoy an experience of traveling back in time to three Tuscan castles. Visit one of the best-known and most admired wineries in the region and worldwide. You'll also experience a winery which operates inside the walls of a medieval fortified village, as well as a third picturesque vineyard and castle.

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Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.5 / 5

based on 160 reviews

Our Guide was simply “Superb” in every way! She was extremely knowledgeable about the wine industry, the countryside and the history of the Castle we visited, as well as, the history of wine growers in Italy! The Location she choose for our lunch in Tuscany, was awesome, the food selection, preparation & taste was incredible. We were served on the patio with an unbeatable view of the winery, and oh, what a charming dining facility! It was my sister & brother-in-law 50th Anniversary, and this tour could not have been more perfect and more memorable! Thank you to everyone!

Fantastic experience !! Alessandro provided solid communication before, during & after our tour. He was on time, provided great information during the different visits and was very attentive to all our questions. As someone that has completed many tours like this, I particularly appreciated the patience with the family (when you have kids!!!) as well as the good driving. Highly recommended !!!

The tour was amazing. We walked for few km but the walk was so relaxing and calm that we didn't even feel tired. Our guide Francesco was simply amazing and we stopped several times to taste the smells of Tuscany, listen to stories about the region. I love this region,I love this walk and the tour. We will do it again for sure!

Very professionally run, lots of facts and history learnt and wine!!!!

We had the best time! The walk was beautiful and our guide taught us lots about the local plants, animals and the history of the trail and the local area!!! Great fun! The wine tasting was also brilliant fun. It was very efficient and everyone involved were fun and helpful. 5 stars ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

A fun and informative day. Our guide, Daniel was very knowledgeable and gracious.