Discover Spain’s Medieval Treasures and Taste Local Wines on a Small Group Journey
Live a two-day journey through the cultural heart of central Spain.
From the ancient Roman aqueducts of Segovia to the storied medieval walls of Ávila, and the timeless beauty of Toledo, this premium experience blends guided discovery, local flavors, and the rich heritage of three iconic cities.
Spend the evening discovering Toledo at your own pace, an enchanting city that truly comes alive by night.
Travel in comfort, enjoy curated experiences with expert guides, and end your journey with an exclusive wine tasting in a picturesque vineyard near Toledo.
This two-day cultural getaway from Madrid takes you through three of Spain’s most historic and awe-inspiring cities—Segovia, Ávila, and Toledo—before ending with a peaceful winery experience in Castilla-La Mancha. With expert-guided tours, free time for personal discovery, and carefully selected accommodations, this short journey is rich in heritage, beauty, and authentic flavor—perfect for travelers looking to go beyond the surface and connect with Spain’s timeless soul.
Discover Spain’s medieval treasures on a full-day journey from Madrid.
Your experience begins early in the morning in Madrid, where you’ll meet your guide at the centrally located Plaza de San Miguel. From there, the adventure unfolds as you travel to Segovia, one of Spain’s most enchanting architectural jewels. Your first stop is the majestic Roman aqueduct, an awe-inspiring feat of engineering that has stood tall for nearly 2,000 years. As you explore the old town, you'll wander its cobbled streets, gaze up at elegant stone buildings, and discover the Alcázar of Segovia—a dramatic castle said to have inspired Disney’s Cinderella Castle.
Next, journey to the walled city of Ávila, a UNESCO World Heritage Site known for its nearly intact medieval fortifications. On your guided tour, you’ll walk along its storied walls, feel the weight of centuries in its Romanesque churches and Gothic cathedrals, and learn about the life of Saint Teresa of Ávila, one of Spain’s most iconic religious figures.
In the afternoon, you’ll arrive in Toledo, a city layered with Christian, Muslim, and Jewish heritage. Here, your cultural immersion continues with a visit to the imposing Toledo Cathedral, a breathtaking masterpiece of Spanish Gothic architecture. As the day winds down and the light softens over the ancient rooftops, the city’s charm deepens. You’ll have free time to explore Toledo at your own rhythm—walk its maze-like streets, watch the sunset from a quiet plaza, or discover hidden taverns steeped in history.
You’ll spend the night in a handpicked boutique hotel nestled in the heart of Toledo’s old town. With its timeless character and central location, it offers not just rest, but the feeling of living within a story centuries in the making.
Sip, savor, and discover the wines of Castilla-La Mancha before returning to Madrid.
Awaken in the magical stillness of Toledo, where early morning light paints golden hues across stone facades and narrow alleyways. After a relaxed breakfast at your boutique hotel, the morning is yours to enjoy at your own pace. Climb up to the Mirador del Valle for sweeping views of the city framed by the Tagus River, sip coffee in a sun-drenched square, or, for the adventurous, hop on an e-bike to explore the surrounding hills and viewpoints. Whether you're drawn to quiet contemplation or movement, Toledo reveals more of itself with every step.
In the early afternoon, it's time to say farewell to Toledo as you journey into the tranquil landscapes of Castilla-La Mancha, Spain’s historic wine country. Rolling vineyards stretch out under open skies as you arrive at a boutique winery chosen for its tradition, charm, and connection to the land.
Here, a guided tour of the vineyard and cellar offers a window into the soul of La Mancha winemaking. Learn about native grape varieties, the rhythms of the harvest, and the techniques that make each bottle unique. Then, settle in for a tasting of three local wines, surrounded by the beauty of the countryside. Each sip tells a story—of sun, soil, and centuries of tradition.
After this relaxed and flavorful experience, you’ll return to Madrid in the late afternoon, carrying with you not only memories of iconic monuments and ancient cities but also a deeper sense of place—and the feeling of having truly tasted Spain.
Ready to start planning your journey? Get in touch with us.
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