The nation’s oldest city, St. Augustine, beckons visitors to discover its charming cobblestone streets, historical landmarks and pristine beaches. Friendly locals, sunny days and lovely places to dine, play and become enlightened, welcome guests year-round. For over 30 years, Old Town Trolley Tours has brought the best of the city to life through Transportainment, our unique blend of transportation and entertainment. Climb aboard to experience the humorous tales and interesting trivia of our friendly conductors, as they bring 500 years of American history to life.