Hole in the Wall Golf Club sits in Naples, Florida, and features a design by Dick Wilson, one of the mid-twentieth century's most prolific architects in the state. Wilson, who worked extensively throughout Florida from the 1950s until his death in 1965, developed a reputation for routing courses that made strategic use of water hazards and native vegetation while accommodating the region's flat terrain. His portfolio includes numerous private clubs across the southeastern United States, many of which remain largely unchanged from their original designs. The course occupies land characteristic of Southwest Florida's coastal plain, where elevation changes are minimal and water management becomes a central design consideration. Wilson typically incorporated lakes, canals, and wetland areas both for drainage purposes and as strategic elements that define playing corridors and green complexes. The layout likely features his trademark bunkering style—often deep, with distinct shapes that frame landing areas and approach shots. As a private club in Naples, Hole in the Wall serves a membership drawn from the area's substantial seasonal and year-round golf community. The club operates within a region known for its concentration of golf facilities, where Wilson's work represents an earlier generation of course architecture that predates many of the resort and residential developments that later transformed the Naples landscape. The course reflects the design sensibilities of Florida golf's golden era, when architects worked with the natural environment rather than attempting to dramatically reshape it.