Trakai, a small town that lies about 17 miles west of Vilnius, is rich in Lithuanian history. It is believed that Grand Duke Gediminas made Trakai his capital in 1321. The first verifiable mention of the town comes from German chronicles of 1337. Gediminas eventually moved his capital to Vilnius and left Trakai to his son, Duke Kęstutis. It was during the residency of Kęstutis that construction began on the first version of the Island Castle, which is today Trakai's main tourist attraction.

Although the castle's location on an island in Lake Galvė added to its security, the fact that it was first constructed of wood did not. The Island Castle, and the nearby Peninsula Castle (only partially restored today) were successfully raided on several occasions by Teutonic Knights during the 14th century. In 1410, the Grand Duchy of Lithuania soundly defeated the Teutonic Knights at the Battle of Grunwald (known as the Battle of Tannenberg in German), ushering in a period of stability at Trakai. At some point in the 15th century, the wooden castles were replaced with more defensible stone versions.

Despite their strengthened defenses, both the Island and Peninsula Castles were destroyed in 1655 during a war with the Grand Duchy of Moscow (Muscovy) and remained in ruins for centuries until some reconstruction efforts began in 1905, at a time when Trakai was ruled by Russia. These efforts, however, soon faltered as more pressing events intervened - World War I and the Bolshevik Revolution. Further efforts began in 1929, but were eventually stalled by World War II. Restoration work resumed, for a time, during the Soviet era, but was halted again in 1961 after Soviet ruler Nikita Khrushchev declared that such work would be a glorification of Lithuania's feudal past. Finally, after independence in 1991, the Island Castle was fully restored to the state we see today.

Aside from its castles and scenic natural setting, Trakai is also known for its once thriving Karaim (Karaite) community. The Karaim were a Turkic speaking group from Crimea (in present-day Ukraine) centered near Bakhchisaray. The Karaim were a Jewish sect that adhered to the Torah (the Hebrew Bible), but rejected the Talmud (later Rabbinical commentaries on the meaning of the Torah) and other interpretations of the Torah. The Karaim conducted their religious services in Hebrew. The Karaim were also known for their imposing physical stature, and it is perhaps for this reason that a group was brought from Crimea in 1400 to serve as royal bodyguards at Trakai. The Karaim eventually became an important part of the Trakai community and economy, but over the centuries, war, repression and their practice of not accepting converts reduced their numbers. Today, of the estimated 10,000 Karaim in the world, only 200 live in Lithuania.