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The History of Charter Boat Row


Some of the “fightingest” fish in the world swim in the waters surrounding Key West. To catch them, anglers often make the wise choice of chartering a fishing vessel run by an experienced, professional captain. In Key West, historic Charter Boat Row in Garrison Bight on Roosevelt boasts the largest fleet of charter boats in Old Town Key West: a long row of seaworthy craft, idle until till they set out again in search of sport fishing action. The type of craft here that are the most imposing, by virtue of their soaring outriggers, and “tuna towers”, are the deep sea fishing “battle-wagons”. They are typically 40-50 feet in length. They range offshore, out to the Gulf Stream, in pursuit of sailfish, marlin, dolphin, and other large ocean-going (pelagic) fish species. These charter vessels and their crews often take center stage when the talk tums to fishing legends. And, it is with their deep sea adventures that this “capsule history” is chiefly concerned.

Jump to the gallery of Vintage Key West Fishing Photos


Charter boat Row was not always a mecca for sports fishers. Its story begins early in the 19th century. Key West was merely an isolated settlement then. Yet, diaries from that time often mention fishing parties that were composed of many of the town’s most prominent citizens. From the downtown waterfront they sailed out in swift sloops and schooners for a day’s sport. The crewmen aboard were probably paid “hands”, not unlike the charter boat crews of today. More to the point, by 1876 at least one owner of a Key West based sloop was offering his vessel for fishing trips at the price of$4.00 per day for charter.

We know little else about the first initiatives to establish charter boats at Key West and the Keys. But, after the tum of the 20th century, the industry began to gather momentum. Tourists were coming to Florida in greater numbers, lured in no small part by tales of the thrills of fishing in bountiful waters. That a number of first class hotels had opened in the “Sunshine State” didn’t hurt.

For example, the Long Key Fishing Camp was completed in 1908. Soon it hosted wealthy anglers eager to cast their bait with the fishing guides and charter boats based there. Similarly, when the Casa Marina Hotel opened in 1920, Key West’s fine fishing was touted as a prime reason for tourists to stay there. By 1923, at least three charter boats were available for hire on the island. The honor of being the first captain to regularly take out charters is harder to determine. Key West residents Begly Filer, Luther Pinder, and Eddie “Bra” Saunders have all been set down in various period sources as being the “first”.

The Charter Boat Row of today was “born” in the 1920’s among the docks and piers of the downtown Key West waterfront. ln those days, several charter boats were tied up along the “Porter Docks at the foot of Duval Street. Boats could also be chartered at the Thompson Fish docks at the foot of Margaret Street and at the nearby Gulf Oil Dock. As the “roaring twenties” drew to a close, the charter crews looked forward to a new decade of giving anglers top notch fishing action. They were in for a disappointment.

The 1929 Stock Market crash spawned a national economic depression that hit Key West especially hard. By the early 1930’s, tourism to the island was almost nil. Other setbacks and natural disasters followed. After 1938, business conditions at Key West improved a little. Tourism picked up. Many charter boats found an additional location at the Craig Docks where the docks of the P&O steamship line at Trumbo Point joined the eastern shoreline of Key West Bight. But, with the onset of WW II, sport fishing was on hold for “the duration.” Some charter crews turned to commercial fishing to make ends meet. Others joined the war effort. As the post-war era (and the subsequent economic boom) unfolded however, the charter boats of the Keys were again being sought out by the angling public. The crews at Key West Bight were eager to oblige, but they had some handicaps.

The Bight left a lot to be desired for the docking of charter boats. It was open on the northwest side to the strong storms of winter. These often played havoc among the craft sheltered there. Then too, the character of the waterfront was changing. For example, the old Gulf Oil Dock was being turned into a bulk terminal for Standard Oil products. Huge oil storage tanks would soon occupy much of the property. More importantly, the Bight was “off the beaten path” of the increasing numbers of tourists coming to Key West via the Overseas Highway.


There was an alternative location to base the Key West charter fleet: Garrison Bight. During much of the nineteenth century, the Army had a garrison post on the western shore of the bight – hence the name. When Henry Flagler’s railroad was extended to Key West, a long, narrow finger of fill was constructed across northern margin of the Bight. This created an enclosed, sheltered basin to the south of the fill: a perfect anchorage for small craft! A gap in the fill, spanned by a swing type railroad bridge) allowed navigation from the basin to outside waters. Although the bridge was long gone by the mid-1940s, Garrison Bight was far from forgotten. Many in Key West saw its potential as a marina and yacht basin. In 1947 the City of Key West bought most of the submerged lands of Garrison Bight from the State of Florida for the sum of $913.00.

The location and its visibility was not lost on the charter captains of Key West. They realized if they moved their boats to the seawall that ran along southern edge of the Bight, and which fronted on North Roosevelt Boulevard, they would be easily noticed by tourists driving into Key West. So, in January 1949, the captains (who had already banded together in 1938 as the Key West Charter Boatman’s Association) leased the portion of the seawall that ran from First Street westwards from the City. Soon, many of the charter boats that had been at the Craig Docks, the Standard Oil dock, and elsewhere, were operating on the seawall. It wasn’t long before crowds of tourists and locals came to “Charter Boat Row” almost every afternoon to check out the day’s catch. Each skipper, of course, displayed his catch on a rack near his boat’s dock. It helped attract anglers.

Eventually, this grew to be too much of a good thing. By the late 1960’s, traffic congestion near the charter docks bordered on being a public safety hazard. The causeway across Garrison Bight had been completed in 1965. In the early 1970’s it was modified to serve as the City’s Municipal Marina. The southern seawall there was available to dock boats. In 1974 the bulk of the charter fleet was prompted to move to that location at the urging of the City. Some captains had misgivings about this relocation. However, these were mostly put aside as the years passed, and “Charter boat Row” flourished anew. It still draws sportsmen from the world over. And so, the legendary status of Key West as “mecca” for those seeking angling thrills continues.

Editor’s Note: This article originally appeared in the summer 1998 issue of the Florida Keys Sea History Journal, the official publication of the all-volunteer, non-profit, Key West Maritime Historical Society.


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