Montespertoli offers more than just beautiful scenery; it’s a hub for authentic, hands-on experiences that connect you with Tuscany’s landscape, wine, and traditions. Whether you want to horseback ride among vineyards, sip organic wines straight from the estate, or relax with yoga and olive oil tasting, this charming town has plenty to offer. We especially love experiences that blend activity with cultural insight, like horseback riding through Chianti’s vineyards and woods, which combines adventure with stunning views. These experiences are ideal for travelers craving something more engaging than a typical wine tour.
Montespertoli’s diverse range of tours makes it possible to tailor your visit to your interests—whether that’s exploring local wines, enjoying outdoor activities, or finding peace on a yoga mat. The following list covers four of the best options, each with its own unique appeal.
1. Chianti: Horseback Riding Through Vineyards and Woods

This horseback riding experience offers an immersive way to explore the Tuscan countryside. Accompanied by qualified staff, you’ll ride through vineyards, olive groves, and enchanted woods in Chianti. The activity caters to both beginners and experienced riders, with a safe, scenic path that makes it accessible to everyone. The company prides itself on being a dream place immersed in the countryside, and the guide’s patience makes it a relaxing, fun adventure.
Reviews highlight the friendliness of the instructors, with one raving, “Instructor so friendly and speaks very good English.” Others appreciated the chance to see a 2-month-old pony during the walk. The one-hour ride offers a perfect snapshot of Chianti’s natural beauty, whether you’re looking for a quick taste of riding or a gentle intro to the region’s landscape.
Bottom line: If you want a gentle, scenic introduction to Tuscany’s outdoors with friendly guides, this horseback ride is a delightful option. It’s good for families or anyone with a soft spot for animals and nature.
2. Fattoria La Leccia: Winery Tour and Tastings in Montespertoli

At number 2 on our list, the Winery Tour and Tastings at Fattoria La Leccia offers a deep dive into organic wine production. For around $41 per person, you spend two hours exploring a farm that produces Metodo Classico sparkling wines entirely on-site, using native grape varieties. The estate is located in one of Tuscany’s most renowned wine-growing regions, ensuring authenticity and quality.
What sets this tour apart is their commitment to sustainability and tradition, with a focus on artisanal methods and local grapes. Visitors get to see the entire process, from vineyard to bottle, and enjoy tastings paired with local delicacies. The estate’s commitment to innovation within tradition makes it a compelling choice for wine lovers looking for an authentic experience.
Bottom line: This tour provides excellent value for those interested in organic wines and traditional Tuscan methods. It’s ideal for curious travelers who want to learn about local wine-making while tasting some of the region’s best sparkling wines.
3. Fattoria La Leccia, Montespertoli: Yoga & Olive Oil Tasting

For a more relaxing experience, the Yoga and Olive Oil Tasting at Fattoria La Leccia combines wellness with culinary delights. Priced at $59 per person, this two-hour session begins with a Kundalini yoga lesson under an ancient holm oak, designed for all levels. Afterward, you’ll enjoy a tasting of extra virgin olive oil and learn about its nutritional and cosmetic benefits.
The experience is held in the farm’s peaceful garden, making it perfect for travelers seeking some tranquility amid Tuscany’s busy sightseeing schedule. The farm’s commitment to educating visitors about local products adds educational value beyond just the yoga session.
Guests describe the atmosphere as “peaceful,” and the experience is especially suited for those who want to unwind and learn about wholesome Tuscan foods. The combination of mindfulness and tasting makes it stand out.
Bottom line: If you’re into wellness, nature, and gourmet foods, this experience is a calming way to connect with Tuscany’s culinary and spiritual traditions.
4. Fattoria La Leccia, Montespertoli: Vineyard Walk & Tasting

Our final pick is the Vineyard Walk & Sunset Tasting, offering a scenic trek through the estate’s organic vineyards. Priced at $53 per person for 2.5 hours, this tour is perfect for those who love combining walking with wine tasting. You’ll stroll through the heart of Tuscan countryside, with panoramic views over the Chianti hills, before settling in for a sunset tasting.
The estate produces organic wines and olive oil, and the walk allows you to see their sustainable farming practices firsthand. The sunset views make this one of the most visually memorable experiences, especially as the light hits the rolling hills and vineyards.
Guests enjoy the relaxed pace and the opportunity to taste estate-grown wines in a quiet, beautiful setting. It’s suited for travelers who appreciate outdoor activity combined with wine and food in a peaceful environment.
Bottom line: If you love walking and want to enjoy organic wines against a stunning sunset backdrop, this experience offers wonderful value and a memorable setting.
How to Choose the Right Experience in Montespertoli
When deciding between these tours, consider your main interests. If you’re after a gentle outdoor adventure, the horseback riding is a great choice. For wine enthusiasts, the winery tour offers a deeper dive into local production. If relaxation and wellness appeal, the yoga and olive oil experience blends gentle activity with gourmet education. Finally, for those who love combining a walk with tasting, the vineyard sunset walk offers scenic views and organic wines in a serene setting.
Compare your budget, time available, and personal interests. For example, if you’re short on time but want a taste of the countryside, the horseback ride is quick and charming. For a more immersive experience, the winery tour provides insight into traditional wine-making methods.
Advance booking is recommended, especially during peak seasons in spring and fall, when vineyard colors and weather are at their best.
Montespertoli’s combination of scenic landscapes, authentic wines, and varied experiences makes it a rewarding destination for many types of travelers. Whether you prefer active pursuits, wine tasting, or peaceful moments, these four tours give you a taste of the region’s best. We suggest booking early to secure your preferred time, and remember—there’s no wrong choice here, only the perfect one for your interests.