This paper presents an investigation of the strategic planning practices of small businesses in Rotorua. The Rotorua district has a population of around 70,000 residents, located in the heart of New Zealand's North Island. Tourism is Rotorua's largest employer contributing around $593 million per year, or 10% of the district's economy. The strong link between planning and performance is understood for larger organisations but less so for small and medium sized firms. This study explores the degree of strategic planning undertaken by Rotorua-based businesses. A combination of quantitative and qualitative data collection via a structured questionnaire and a semi-structured interview, comprised the research methodology. Collected data was analyzed using advanced machine learning ( classification) techniques. Findings suggest, a firm's industry sector influences the degree of formal planning. Other factors that influence the degree of planning formality include the age of the business, annual revenue, and the number of employees. More significantly, this study observes that formal business training and an age of a business are two features responsible for separating more formal planners from less formal planners.