
by Donald E. SheppardThe King's Comptroller, Juan de Anasco, was dispatched from Cuba to explore Florida's coast during the year before DeSoto sailed from Havana. Anasco found Ponce de Leon's Charlotte Harbor and took some Indians from Chief Hirrihigua's village, Ucita, at the head of it. Anasco was licensed by the King to barter with them. They trapped fish in the harbor and traded them with inland Indians. Anasco envisioned developing that trade with Havana, which Cabeza de Vaca reported to lie 100 leagues due south of there. It measures 265 miles sailing around the Key West reefs. Hirrihigua's gigantic stone fishing enclosure is still there, hooked southward into the bay at the head of Charlotte Harbor. It may be the oldest "historic" structure in the United States.
Anasco's captives knew the shoreline and could locate their home port on their return with DeSoto's fleet. Their village, Ucita, would become DeSoto's base of operations. Narvaez had been through that village, cut off Chief Hirrihigua's nose, then proceeded inland. Juan Ortiz had been there and fled for his life.
Before his return to Cuba, Anasco carefully sounded the harbor, noted the tide's effect on it, then measured the distance back to Havana via Dry Tortuga; 75 or 80 leagues, as reported to his officers in Havana. He advised DeSoto to sail on May 25th to catch the Full Moon and Spring Tides at arrival, but DeSoto chose to sail on favorable winds and New Moon tides instead, one week early.
The men sighted Florida to the north on May 25th, ten leagues west of the Bay of Juan Ponce, but the transport captains would go no closer than one or two leagues from land until sighting the harbor entrance. They reported the coast in four brazas water (22 feet deep) on a northern landfall, and dropped anchor 4 or 5 leagues below the port. That depth of water, that close to land, 75 or 80 leagues north of Havana, ten leagues west of the Bay of Juan Ponce on a northern landfall, 4 or 5 leagues below a port, occurs at only one place in Florida: Sanibel Island.

DeSoto, his guard, Anasco and the captives were transferred into DeSoto's smaller brigs to find the harbor that evening, leaving the cumbersome transport ships at anchor. If the fleet over-shot the harbor the large ships could not tack back to it against the high southerly winds, which were reported, to enter the harbor's pass. To preclude that, DeSoto coasted downwind, northward, in his small, maneuverable brigs, advancing to where he thought the harbor's entrance was located. He sailed out of sight of the fleet, however, which had moved out into deeper water for safe overnight anchorage. That evening DeSoto found Charlotte Harbor's entrance at Boca Grande Pass, but was kept from returning to the fleet by darkness and wind. DeSoto spent the night at a deserted Indian village, probably on Useppa Island, much to the chagrin of his people.
The next morning, DeSoto sailed back out the pass to explore the enormous sand bar at the harbor's entrance and to summon the fleet. He was spotted four leagues downwind of the fleet's anchorage as he tacked across the high winds. The fleet advanced downwind between vessels DeSoto stationed on either side of the narrow channel to guide the fleet into the harbor. Two of the fleet's ships scraped sandy bottom as they entered.
Since they had left Havana a week earlier than Anasco had advised, DeSoto's fleet could not enter the harbor's shallow channel just south of Cape Haze, despite efforts to do so. They were forced to anchor two leagues inside the pass, in deep water, to wait for Spring Tides. Those tides of Full Moon were five days away. While they waited the men comforted the horses with fresh foliage and berries from the islands and bays west of Cape Haze, just to the north of their anchorage. Twenty horses perished before they were landed, however, and Anasco was publicly scolded for the delay which may have contributed to their injuries. Anasco had warned DeSoto about the harbor's shallows before leaving Havana, however, thereby establishing May 25th as the proposed departure date to hit Spring Tides on arrival; a date formally acknowledged by DeSoto.