St Augustine has been going since 1565, when the Spanish admiral Pedro Menéndez de Avilés landed and founded a settlement, which makes it the oldest continuously occupied European-founded city in the contiguous United States. That is more than half a century before the Pilgrims. The Spanish held it, lost it to the British, got it back, and finally ceded Florida to the United States in 1821, and the layers of all those flags show in the old street plan, narrow and tight, running between coquina-stone and stucco buildings.
The great landmark is the Castillo de San Marcos, a star-shaped fortress finished in the late seventeenth century and built from coquina, a soft limestone made of compressed shells. When English cannon balls hit it in a siege in 1702, they stuck in the stone rather than shattering it, which is exactly the story the guides like to tell. You can walk the walls and look across the Matanzas River toward the lighthouse on Anastasia Island. The town also owes a lot to Henry Flagler, the oil tycoon who built grand hotels here in the 1880s and a railway down the coast, and whose Ponce de Leon Hotel is now part of Flagler College. A well-known spring claims to be the Fountain of Youth, for the explorer Juan Ponce de León, who landed on this coast in 1513. The claim is more cheerful than historical.
For a rider the town is a place to arrive slowly. The Bridge of Lions brings Highway A1A over the Matanzas from the island, and the old centre is a grid of narrow streets full of tourists, horse-drawn carriages, trolleys, and one-way systems. The pavement is uneven in places, and parking for motorcycles is easier than for cars, but still crowded at weekends. The coastal run of A1A north and south is flat, easygoing and often right on the dunes, with good views of the sea and a warm, salty smell in the air. Summer thunderstorms are frequent, and winter is mild and the best time to ride.
St Augustine has everything: petrol on the main roads, seafood restaurants, ice cream, coffee and plenty of places to sleep. Park near the old Plaza, walk the length of St George Street, and give yourself time for the fort. The town is crowded at midday and quieter in the evening, when the old buildings glow in the lamplight.