There are 355 sleeps (355 days) until October 14 (Thursday, October 14, 2027).
There are 355 days until October 14 (Thursday, October 14, 2027) — one sleep per night.
One sleep per night between now and the big day — tonight is the first sleep, and the morning after the last sleep is October 14. Sleeps are the same as days.
355 sleeps is 50 weeks and 5 sleeps.