Fly to Kingston, Jamaica, and take a public bus or private taxi to the Spanish colonial capital of Jamaica, which is today known as Spanish Town. This settlement, which now lies within St. Catherine's parish about 10 miles from Kingston, was founded as Villa de la Vega by Francisco de Garay. A damaging siege by the English in 1655 resulted in widespread destruction of the town and the English conquest of the island, after which the governor's seat was moved to Port Royal. Spanish Town as gradually rebuilt and again became the capital in the late 17th century. Visitors strolling through Spanish Town enjoy an escape from the commercialized tourism typical of many areas in Jamaica and can explore colonial-era streets and houses.
To travel legally to Cuba, obtain a visa from the government of Cuba through the Cuban Embassy. U.S. regulations require you to be a close relative, researcher, journalist, or government worker traveling on official business. Havana was the capital and principal city of Cuba, Spain's prize possession in the Caribbean region. During the 17th century, as rivalry over Caribbean colonies flared between Spain and England, several strongholds were built around Havana Bay, including San Salvador de la Punta and the Morro Castle. These have remained the most important historical attractions for visitors.
Drive to St. Augustine, on the northern Atlantic coast of Florida (the nearest large airport is in Orland). This is the oldest Spanish settlement in North America, founded in 1565 by Don Pedro Menendez de Aviles. Menendez drove out the French but had to defend St. Augustine against English pirates. To protect the settlement, the Spanish raised the Castillo de San Marcos, which still stands at the northern edge of St. Augustine's historic quarter. Since its construction in the late 17th century, the castle has never fallen to an enemy siege, and offers visitors a fascinating glimpse into military architecture and lifestyle of the Spanish colonial era.
Fly to the South American nation of Colombia for a look at the Spanish homes and fortifications of Cartagena de Indias, a coastal settlement originally founded in 1533 by Pedro de Heredia. Subject to frequent attacks by English privateers, the city was fortified with San Felipe de Barajas, an imposing fortress. The colonial walls, gates, palaces, and plazas that draw large crowds of visitors from Colombia and around the world have earned Cartagena the designation of UNESCO World Heritage Site.
