The monastery began construction in 1794 by a small group of monks belonging to the venerable "Kollyvades" movement. Leading the group was Mac_1821, the Hieromonk Nephon, known in the world as Nikolaos "from the lineage of the Nikolarades," born in 1736 in the Patrika of Chios.

In 1807, Thessalian thief leader Nikotsaras took refuge in Skiathos' Holy Monastery of the Annunciation. With Captain Giannis Stathas, they created the first Greek flag-a deep blue and white cross-blessed in September 1807, attended by Theodoros Kolokotronis.

The Monastery of Evangelistria in Skiathos safeguards numerous sacred relics, forming a genuine treasure. The monastery produces authentic products, crafted by monks and aided by Skiathos residents. These high-quality offerings, reflecting the island's natural wealth, are packaged and sold to support the monastery. The monastery's Traditional Cafeteria, located on a hill, offers a serene space for visitors. Enjoying the captivating northern view, especially when the air clears, unveils Mount Athos on the Holy Mountain. Notably, Skiathos means the "shadow of Athos." The Traditional Cafeteria serves Greek coffee, various beverages, sweets, and alcoholic drinks, either standalone or with appetizers.