Tamiami Trail

US-41's Tamiami Trail runs 284 miles between Tampa and Miami, but riders mean the roughly 95-mile Miami-to-Naples stretch across Big Cypress National Preserve and the Everglades. Only about 15 bends break the line — straight as an arrow, built in 1928. Flat and two-lane, with sawgrass and cypress to the horizon and herons working the canal alongside the road. The longest fuel gap runs about 40 miles, so top off before the Everglades City side. Traffic thins fast once you clear the Miami suburbs. Stop at the Ochopee Post Office, the smallest in the country, running from an old irrigation shed since a 1953 fire, and the site of Monroe Station, a 1928 motorist waystation that burned down in 2016. Pair the crossing with the Overseas Highway for a full South Florida loop. Riding it, start to finish: 1. Start in Miami and head west on US-41 (Tamiami Trail) toward Naples. 2. Cross 95 miles through Big Cypress National Preserve and the Everglades with minimal traffic once clear of Miami suburbs. 3. Top off fuel before entering the Everglades — the longest gap runs about 40 miles. 4. Stop at the Ochopee Post Office, the smallest in the country, housed in an old irrigation shed since a 1953 fire. 5. Pay respects at the site of Monroe Station, a historic 1928 motorist waystation that burned down in 2016. 6. After Naples, pair this crossing with the Overseas Highway for a full South Florida loop.