Two saildrones participated in the Salinity Processes in the Upper-ocean Regional Study 2 (SPURS-2) field campaign at 10°N, 125°W, as part of their more than six-month Tropical Pacific Observing System (TPOS)-2020 pilot study in the eastern tropical Pacific. The two saildrones were launched from San Francisco, California, on September 1, 2017, and arrived at the SPURS-2 region on October 15, one week before R/V Revelle. Upon arrival at the SPURS-2 site, they each began a two-week repeat pattern, sailing around the program’s central moored surface buoy. The heavily instrumented Woods Hole Oceanographic Institution (WHOI) SPURS-2 buoy serves as a benchmark for validating the saildrone measurements for air-sea fluxes. The data collected by the WHOI buoy and the saildrones were found to be in reasonably good agreement. Although of short duration, these ship-saildrone-buoy comparisons are encouraging as they provide enhanced understanding of measurements by various platforms in a rapidly changing subsynoptic weather system. The saildrones were generally able to navigate the challenging Intertropical Convergence Zone, where winds are low and currents can be strong, demonstrating that the saildrone is an effective platform for observing a wide range of oceanographic variables important to air-sea interaction studies.