Siena, Tuscany Tours & Activities in 2026

Siena , Tuscany

From $ 80.29

Paradiso di Cacuci is a winery located in a small “corner of Paradise“ in the northwestern area of ​​Montalcino. Our wine production is centered on the perpetuation of the tradition which, together with a more modern model and in compliance with the values ​​of the Brunello Consortium, uses only from our vineyards which are respectively divided into; 5 ha Brunello di Montalcino, 1 ha. Rosso di Montalcino and 5 ha. di I.g.t. Sangiovese. Welcomes, by reservation, individual visitors and small groups offering guided tastings that give the opportunity to get to know the production directly, starting from the winemaking process to the discovery of the final result, giving a unique and unforgettable experience. Our tastings are only private and by appointment only to guarantee you our best services.

Siena , Tuscany

From $ 40.73

- Immerse yourself in the world of Tuscan wine with our comprehensive tasting experience. - Master the art of tasting: Learn professional wine and extra virgin olive oil tasting techniques. - Discover Chianti's soul: Explore the region's rich wine culture, terroir, and the iconic Sangiovese grape. - Uncover the Super Tuscan legend: Understand the origins and evolution of this revolutionary wine style. - Savor exceptional wines: Taste our full range of organic wines, including an award-winning Super Tuscan and rare native grape varieties. - Guided by experts: Benefit from the knowledge of our certified wine guides. - Elevate your palate and expand your wine knowledge in an unforgettable wine and food experience.

Siena , Tuscany

From $ 91.92

Depart from Siena and enjoy a full-day tour to Pisa, San Gimignano, and Chianti. Savor a traditional lunch at a Chianti winery with antipasto, fresh pasta, dessert, and a tasting of 3 local wines.

Siena , Tuscany

From $ 65.16

Enjoy a unique lunch experience in the picturesque setting of the Poggio ai Laghi vineyard, paired with Wine Tasting and a great Wine Expert who will guide you through this excellent experience.

Siena , Tuscany

From $ 65.16

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that includes Truffle, Chili Pepper, and Extra Virgin Olive oil. Aceto Balsamico tasting that includes Onion and Modena vinegars. Tuscan appetizers: Salame toscano, finocchiona, prosciutto crudo toscano, pecorino, bruschetta with fresh tomato and basil, cialda di pane tostato with Extra Virgin Olive Oil. First course: Penne al ragù or Penne al pomodoro. Second course: Arista with roasted potatoes. Dessert: Cantuccini and Vinsanto

Siena , Tuscany

From $ 69.81

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti. Vineyard Walk: Self-guided stroll through scenic vineyards before or after your tasting. Guided Tasting 4 carefully selected organic wines 4 artisanal local cheeses Fresh fruit, honey, and jams to enhance the tasting experience Expert explanation of pairing principles: acidity, tannins, structure, fat, and sweetness Professional Guidance All experiences are led by our certified Sommelier, providing insider knowledge and tips. Educational Materials Receive presentations and infographics designed to deepen your understanding of wine & cheese pairing.

Siena , Tuscany

From $ 75.63

Discover the authentic beauty of Tuscany with our tour of vineyards, art and flavours. We begin with a walk through the vineyards, immersed in the heart of Chianti, to reach the charming little church of San Giorgio a Lapi, dating back to 1100. Here you can admire three splendid frescoes by Nasini, a true hidden gem. After the visit, we will enter our cellars to discover the winemaking and aging process of the wine. And to end in style, a tasting awaits you on our panoramic terrace, overlooking the Crete Senesi, accompanied by a lunch with the best typical Tuscan products, all in the shade of an ancient white mulberry tree. Live an unforgettable experience between nature, history and good wine!

Siena , Tuscany

From $ 88.77

This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist. After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.

Siena , Tuscany

From $ 89.01

Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

Siena , Tuscany

From $ 38.40

Imagine finding yourself on a panoramic terrace, surrounded by the beauty of the Chianti hills and the Crete Senesi, in the shade of a white mulberry tree that frames you. Here, in front of the historic 1100s church, you have the opportunity to participate in an exclusive tasting of three of the most prestigious wines of our production paired with typical Tuscan dishes. This experience is not only a journey into taste, but also an immersion in local traditions, discovering how every sip tells the story of this land rich in culture. Ideal for families, friends or couples looking for unforgettable moments together.

Siena , Tuscany

From $ 57.02

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Siena , Tuscany

From $ 65.16

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves and roads with cypress trees. See and touch the flora and fauna of the Sienese countryside with a guide who will explain the various plants and animals and the history of the places you will encounter during the tour. The walks in the Sienese countryside are suitable for everyone, from beginners to experts. The horses used for the tours are well trained and calm, suitable for everyone. Stop for a picnic in the shade of the river in the Siena area or for a tour and tasting in a winery. Spend an unforgettable day and discover Tuscany with different eyes as you ride your horse, seeing and touching the historic countryside and traditions of Siena.

Siena , Tuscany

From $ 69.81

Exclusive visit to a historic cellar and olive mill Learning approach to tasting and organic winemaking Chianti & Supertuscan tasting, professionally paired with typical Tuscan products. Best Shipping all over the USA and Europe.

Siena , Tuscany

From $ 44.22

Our experience is fully interactive: you'll taste, compare, and learn hands-on how to pair wine and food. You'll master three key pairing techniques, easily applicable to any cuisine worldwide. Discover Tuscany’s wine culture from local producers and enjoy a carefully crafted five-course tasting menu. Vegetarians are welcome—let us know in advance about any dietary restrictions.

Siena , Tuscany

From $ 51.20

A special experience in a unique place: a "vertical” wine of "Le Chiuse" winery of Montalcino, our family's winery. You will taste the youngest wine "Arpaia" which is not yet suitable for aging, the "Rosso di Montalcino" which has a short aging and the "Brunello di Montalcino" with an aging of at least 5 years. We will offer you typical Tuscan fresh products in the frescoed sitting room, under the 5 meters vaulted ceiling. In case of good weather, we’ll show you an unforgettable panoramic view upstairs!

Siena , Tuscany

From $ 52.36

Highlights - Historic Estate Tour: Guided 90-minute visit of Montechiaro Villa (since 1760), including the original wine cellar, aging rooms, and ancient olive mill. - Vineyard Walk: Self-guided stroll through scenic vineyards before or after your tasting. - Seated Wine Tasting: Enjoy four organic wines, including our signature Chianti and award-winning Super Tuscans. - Food Pairing: Traditional Tuscan delicacies perfectly matched with each wine. - Personalized Experience: Our expert Sommelier adapts the tasting to your preferences.