Sleep characteristics may be affected by daytime experiences, a fact that can be leveraged by non-pharmacological interventions to improve sleep. The effect of daily experiences on sleep has been only sporadically investigated in the previous literature, mainly with small interventional studies. In this study, we leverage BSETS, a large multiday observational study (N = 1901 nights in total) with extensive daily diaries and mobile EEG recordings conducted for at least 7 days per participant to investigate how naturally occurring daily experiences affect sleep during the subsequent night. The strongest influence was on the timing of sleep onset: even after controlling for day of the week, sleep onset occurred later after more intense days and pleasurable activities. After statistically accounting for this extended wakefulness, we found limited evidence that daily experiences influence sleep characteristics. Only four effects survived correction for multiple comparisons: sleep and N3 duration were longer after days with time at the workplace, REM latency was increased after social activity, and sleep onset latency was reduced after alcohol consumption. Our work shows that, aside from homeostatic effects resulting from extended wakefulness, sleep is relatively resilient to and only affected by a few distinct daytime experiences. Non-pharmacological interventions seeking to change sleep may need to utilize behavioral modifications outside the normally observed range.