This study investigated contents of training sessions from 387 regular swimmers involved in a recreational workout without supervision. We did use multiple correspondences analysis in order to identify self-trained swimmers typology in a sample from a social networking website, focusing on swimming practice. Self-reported parameters (n = 12) were age, gender, practice frequency, supervision in physical activity experiment, main training target, main reason for swimming choice, swimming session duration and distance, most used swimming stroke and material, quality of the training control, and training evolution during a year. Results have highlighted different training strategies and targets according to gender and age. Male strategy consists in performing higher distance (1818.8 ± 644.5 m vs. 1453.0 ± 603.3, p < 0.05 for male and female respectively) by using several swim stroke and gears involving upper body muscles (front crawl, pull buoy and paddles). More concerned about duration of their sessions, women are mainly using breaststroke. Backstroke is associated with people aged higher than 50. We also have established a connection between motives according to ages and long term strategies. The main motivation for middle aged people appears to be general health benefits by performing identical swimming session without evolution during a year. People aged from 20 to 30 are divided between an identical swimming session strategy and an increase in distance or in intensity strategy during a year. This population appears to be concerned about a global health benefits and a body shape effects. Suggestions are made to improve swimming practice environment during free time sessions according to the main results.