Northern Europe during the 1400's. Colored area is the extent of Hanseatic League.
A commercial and defensive union of merchant guilds and market towns, growing from a few North German towns in the 1100's the Hanseatic League came to dominate Baltic maritime trade for three centuries and the League became a "superpower" of the Late Middle Ages. Merchants established the League to protect the guilds' economic interests as well the diplomatic privileges in their home cities and countries, to guard and make secure the trade routes used by the Hansa merchants in land and sea.
The Hanseatic cities had their own legal system and they operated their own armies for mutual protection and aid. However, only a few cities enjoyed of liberties, autonomy or could be called free city-states.
Hansa's decline is dated back to the Age of Discovery, especially to the discovery and exploration of the Americas which meant the global trade concentrating to the Atlantic Ocean. Meanwhile Hansa lost its possession in Baltic maritime trade to Denmark and Sweden, as well in the North Sea for the English and the Dutch. Also, the European convert in religion affected to Hansa's decline. The Catholic Fate disappeared from the Northern Europe - eating meat was not allowed during Lent in the Catholic Europe, but was replaced with fish. Hanseatic League controlled the fish markets in the Baltic, but while the Catholicism tailed off, the League lost an important trade product.
Instead of just watching its sea-might and maritime trade disappearing in the Northern Europe, losing prestige and national score for the other rising Northern European nations, what if the Hanseatic League would had pursued for establishing a confederation of city-states - Hanseatic Confederation? Would it had the resources to fight for its status, join for the race of supermacy in the Americas and Caribbean, establishing herself as a colonial power replacing the lost Baltic trade with the Atlantic trade?