City & Culture Tours & Trips in Florida

These multi-day Florida cultural tours wind their way through the state's diverse heritage, starting in Miami's vibrant Little Havana, where Cuban influences come alive through traditional coffee windows, art galleries and also music venues. The journey continues to St. Augustine, where costumed interpreters at the 17th-century Castillo de San Marco fort share tales of colonial life, before heading to Key West to explore Ernest Hemingway's home and presidential connections at Harry Truman's retreat. Our customers especially appreciate experiencing the contrasts - joining Art Deco walks through Miami Beach, then watching sunset performers at Mallory Square later that evening. Time in Miami's Wynwood district lets you discover the evolving arts scene, while special access to Edison's winter estate in Fort Myers adds historical depth. Some departures align with St. Augustine's enchanting Nights of Lights, when three million white bulbs transform the colonial streets into a Spanish-inspired holiday spectacle.