Our journey begins with pickup from your hotel in Plovdiv. During the short drive to our first stop, your guide will introduce you to the fascinating history of Bulgaria — one of the oldest countries in Europe.
We will pass through the charming town of Asenovgrad, where you will hear interesting stories about the town and what it is famous for.

Our first stop is the medieval Asen’s Fortress — a remarkable example of Bulgarian medieval architecture and a symbol of the power of the Bulgarian Empire during the Middle Ages. Perched high above the valley and surrounded by breathtaking views of the Rhodope Mountains, you will admire the fortress while learning about its rich history.
You will also hear the fascinating legends of the Rhodope Mountains — the mystical land of Orpheus. Discover the rich flora and fauna that make this mountain one of the most diverse natural regions in Bulgaria. Surrounded by forests, cliffs, and spectacular landscapes, the Rhodopes reveal their unique beauty, ancient stories, and deep connection between nature and mythology.

Our next stop is Bachkovo Monastery — the second largest monastery in Bulgaria. Nestled among the gentle hills of the Rhodope Mountains, this sacred place preserves centuries of history, faith, and legends.
Here you will learn about the Christianization of Bulgaria and the creation and spread of the Cyrillic alphabet, which played a key role in the cultural and spiritual development of the Slavic world. The monastery is also famous for its miraculous icon of the Virgin Mary, believed to have healing powers and deeply revered by pilgrims. Walking through the peaceful monastery complex, you will discover beautiful frescoes, ancient traditions, and a spiritual atmosphere that has attracted visitors for centuries.
Finish the tour with a wine tasting experience in a small family winery near Asenovgrad.

Enjoy a guided tasting of three local wines while learning about the deep traditions of winemaking in this region. Wine has been produced in Bulgaria since ancient Thracian times, when the Thracians were known as skilled winemakers and worshippers of Dionysus, the god of wine.

Discover the storey of the famous Bulgarian grape variety Mavrud, strongly connected to Asenovgrad, often called the “town of Mavrud.” Your host will share the traditional methods of wine production that have been passed down through generations.

You will also learn about the cultural connection between wine and Christian traditions in Bulgaria, where wine has played an important role in religious rituals and monastic life for centuries.

This authentic experience offers a perfect ending to the tour, combining ancient history, local culture, and the rich wine heritage of the Rhodope region.