Times Square to South Beach: What to Ride, Where to Stop

Start at Times Square and Lynn Hall Memorial Park: people-watching, the pier, and more live music than you can shake a coconut at. From there, Estero Blvd is your runway.

Northbound, Bowditch Point is the mellow sunset pick. Mid-island, DiamondHead and the big resorts make easy pickup points. Southbound, our coastal cruiser covers Fairweather Street down toward Publix and 7-11—$4 to $10 a person depending how far you ride.

Bridge TRiPPiN links the island to the mainland for $5 each way, with stops at Margaritaville and Lighthouse Tiki Bar. If you want to bar hop without hunting parking, say the word—unlimited sing-along hops are part of the wristband life.

Every journey with TRiPPiN RiDeS is a chance to see the beach, not the dashboard. Let’s map unforgettable memories together.