The range of small, electrically powered UAVs is still limited by the mass specific energy of batteries. This paper investigates the idea that, in cases where multiple aircraft must transit to the same location, savings in mass or an extension of achievable range are possible when they join wingtip-to-wingtip. The viability of joined flight is investigated by quantifying the relative magnitude of savings resulting from increased aerodynamic efficiency and that of penalties due to the increased structural and component weights. Through a parametric analysis the level of savings achievable is found to be greatly dependent on the proportion of the flight spent in a joined configuration and aircraft design parameters such as wing loading, aspect ratio and the added weight of the joining mechanism. A custom, multidisciplinary UAV sizing algorithm is presented and utilised to design several sample aircraft, featuring two different joining mechanism architectures. The results verify the findings of the parametric study and indicate that mass savings are possible only for moderate to low aspect ratios, with semi-permanent magnetic joining mechanism performing better than rigid structural ones, even when the joined fight segment accounts for only 30% of the total airborne time.