This paper describes an optimal sampling approach to support glider fleet operators and marine scientists during the complex task of planning the missions of fleets of underwater gliders. Optimal sampling, which has gained considerable attention in the last decade, consists in planning the paths of gliders to minimize a specific criterion pertinent to the phenomenon under investigation. Different criteria (e.g., A, G, or E optimality), used in geosciences to obtain an optimum design, lead to different sampling strategies. In particular, the A criterion produces paths for the gliders that minimize the overall level of uncertainty over the area of interest. However, there are commonly operative situations in which the marine scientists may prefer not to minimize the overall uncertainty of a certain area, but instead they may be interested in achieving an acceptable uncertainty sufficient for the scientific or operational needs of the mission. We propose and discuss here an approach named sampling on-demand that explicitly addresses this need. In our approach the user provides an objective map, setting both the amount and the geographic distribution of the uncertainty to be achieved after assimilating the information gathered by the fleet. A novel optimality criterion, called , is proposed and the resulting minimization problem is solved by using a Simulated Annealing based optimizer that takes into account the constraints imposed by the glider navigation features, the desired geometry of the paths and the problems of reachability caused by ocean currents. This planning strategy has been implemented in a Matlab toolbox called SoDDS (Sampling on-Demand and Decision Support). The tool is able to automatically download the ocean fields data from MyOcean repository and also provides graphical user interfaces to ease the input process of mission parameters and targets. The results obtained by running SoDDS on three different scenarios are provided and show that SoDDS, which is currently used at NATO STO Centre for Maritime Research and Experimentation (CMRE), can represent a step forward towards a systematic mission planning of glider fleets, dramatically reducing the efforts of glider operators.