Siena
Castle & Palace Tours

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Our most recommended Siena Castle & Palace Tours

From Siena: San Gimignano, Montalcino & Wine Tasting

1. From Siena: San Gimignano, Montalcino & Wine Tasting

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers, a UNESCO World Natural and Cultural Heritage Site. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation. The final stop of the day will be a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines. Sample other typical local products as well.

From Siena: Chianti and Castles Tour with Wine Tastings

2. From Siena: Chianti and Castles Tour with Wine Tastings

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Explore the gardens of the Brolio Castle and visit the Castellina in Chianti before enjoying wine and local product tastings at 2 wineries in the Chianti area. The beautiful ruby-red color and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine results from the wise blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. On this trip, discover the breathtaking, uncontaminated landscapes that have been cradling the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in the hills of this region. The sounds, scents, and flavors of this land will capture your senses through a unique experience. Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. The tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and join a guided walk of the castle gardens. When the tour of the garden ends, join a wine tasting paired with typical Tuscan food. Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

Medieval Castles & Chianti Wine Tasting Tour with Lunch

3. 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.

Siena: Half-day Guided Hike to Monteriggioni

4. 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.

Chianti and Castles Tour From San Gimignano

5. Chianti and Castles Tour From San Gimignano

Experience the region of Chianti and immerse yourself in picturesque Tuscan scenery on this guided, multi-stop trip from San Gimignano. Visit ancient churches, medieval castles, and small villages where the rhythms of traditional life remain unaltered. Stop at 2 wineries for tours and tastings. Explore the home of one of the most famous wines in the world, with its beautiful ruby-red color and characteristic violet-scented bouquet: Chianti. This wine results from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. Get picked up directly from your accommodation in San Gimignano, then set out to discover the breathtaking landscapes that have cradled the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in this region. After some sightseeing, the tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and you'll take part in a guided tour of the castle gardens. When the tour of the garden ends, enjoy a tasting of two different wines. During this tour, you'll see the characteristic Castle of Brolio from the outside as well as the inner garden of the castle. Later, move on to another winery in the middle of the Chianti Classico area, where you'll savor a second wine tasting paired with extra virgin olive oil. The tour ends with drop-off back in San Gimignano.

Antinori Winery & Brolio's Castle: Private Tour

6. 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.

Chianti Countryside Full-Day Tour by Vintage Fiat 500

7. Chianti Countryside Full-Day Tour by Vintage Fiat 500

Get behind the wheel of a restored Fiat 500, and experience the beauty of the Tuscan countryside from the seat of one of Italy’s most iconic automobiles. Depart for the rolling hills of the Chianti wine region and enjoy views of the vineyards, medieval villages, and lush woodlands of Tuscany along the way. Each vehicle has been immaculately restored with great attention to detail, preserving the unique qualities that made the original Fiat 500 so simple to drive. Follow your professional tour escort to some of the most beautiful spots of Tuscany, stopping for a light lunch at a Chianti winery to complete your day.

Florence: Experience Siena, San Gimignano, and Chianti

8. 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.

Chianti: Private Tour & Wine Tasting at Castle-Wineries

9. 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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What people are saying about Siena

Overall rating

4.5 / 5

based on 160 reviews

A wonderful tour! We had a lot of fun and joy with our guide Kiko. Kiko went to great lengths to bring the country and the people closer to us. It was very exciting to learn things from the past and from the present time. Wild herbs along our hike on the pilgrimage route and anecdotes from the past made the hike very entertaining. The path was very pleasant to walk. In Monteriggioni we had a very nice wine tasting. We really liked the wine, so we even ordered delivery to our home. Afterwards we had a very good meal in the nice little place. We would have loved to have stayed there. I highly recommend this tour! Thank you dear Kiko!

Overall amazing experience! Our guide was very knowledgeable and picked us up on time. The winery tours were fantastic. Would recommend to anyone visiting the chianti area.

Daniel was an excellent guide, we enjoyed every stop of the tour and look forward to recommending it to our friends.

The best tour ever!! Our guide even added a stop to another very tiny Tuscan town.

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