Um, I forget which two ladies asked questions about dealing with hotel roommates and doing water sports while trying to conceal their hair loss. I finally came out to my friend before the trip because it would be several days in a hotel together..But there was nooo way I was going to show my head. (Especially since the husband showed up). I just got ready in the bathroom with my hat/scarf/bandanna for the day, got ready for bed in the privacy of the bathroom, and just wore a real light, cotten, hooded zip up, and slept completely under a sheet. How did I explain all that? Hmm, they didn't think the hoodie was weird because it was cute and comfortable looking. And I just said it's a habit to sleep completely undercover, but it was a sheet so it's not like I was suffocating myself. When we went out somewhere particularly nice was when I spent a crapload of time in the bathroom fixing my hair, but if you are dealing with wigs/toppers then it shouldn't take long at all. If you have no hair, then I'd wear an old wig and wear one of those elastic headband scarfs where the top part can be folded out into a bandanna, make it a point to wear it when you're washing your makeup off, and later if they ask you why you still have it on, just say that you like to sleep with your hair off your face. As for snorkeling, I don't think it's weird at ALL to wear a swim cap. I think that the elastic headband scarf/bandanna works really well in this situation too. Make it real snug on your head, and secure an elastic band around your hair and the fabric that hangs in the back. Then the scarf won't float around in the water as much. This technique also works well when you're wearing bandannas on a windy day and you don't wear it like a 'thug'