12 Best Road Trip Routes in the US — With Estimated Costs

6. Overseas Highway (Florida Keys) - $1,200-$2,000 for 5 Days

The Overseas Highway stretches 113 miles from mainland Florida to Key West, creating one of the world's most unique driving experiences as it hops across 42 bridges connecting a chain of tropical islands surrounded by crystal-clear waters and vibrant coral reefs. This remarkable route, built partially on the foundation of Henry Flagler's historic Florida East Coast Railway, offers an escape to a distinctly Caribbean atmosphere without leaving the continental United States, featuring world-class fishing, diving, and water sports alongside a laid-back island culture that celebrates both American and Cuban influences. The journey typically requires 4-6 days to experience properly, allowing time for snorkeling or diving at John Pennekamp Coral Reef State Park, exploring the artistic community of Key Largo, experiencing the party atmosphere of Duval Street in Key West, and enjoying fresh seafood at waterfront restaurants throughout the island chain. Budget considerations for the Overseas Highway include fuel costs averaging $100-150 for the relatively short route, accommodation ranging from $120-350 per night with premium rates during peak season (December-April) and special events like Fantasy Fest, and dining expenses of $50-80 per day featuring fresh seafood, Key lime pie, and Cuban-influenced cuisine at establishments ranging from casual conch shacks to upscale waterfront restaurants. Activity costs include glass-bottom boat tours ($25-40), snorkeling excursions ($45-75), fishing charters ($150-400 per person), and attraction fees like the Ernest Hemingway House ($15) and Dry Tortugas National Park ferry ($180 per adult), while free activities include beach time, sunset celebrations at Mallory Square, and exploring the unique architecture and gardens throughout the Keys. The total estimated cost ranges from $1,200-2,000 for two people, providing excellent value for a tropical escape that combines natural beauty, water recreation, and vibrant local culture in one of America's most distinctive destinations.