Honestly, my first hurdle is still just getting comfortable enough to wear a thong in the first place. That’s step one for me.
What I’ve gathered from this discussion is context matters. Beach tiki huts on Orient Beach, totally okay and potentially common. Same with some cruise ship bars (probably depends on cruise line too) that are basically part of the pool deck; I’ve definitely at least seen guys in speedos and women in thongs.
A more family-oriented area or beachside bars that aren’t literally on the sand, probably not okay. There’s a lot of gray area here. Might be a read the room.
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In my travels I’ve been to countries where the men do not wear shorts, always long pants. When staying at small hotels those places, put on shorts to go to the poolside bar. I consider it respect for the locals.
For me it varies greatly depending on the setup. I tend to avoid places that have the restaurant right on top of the pool for this reason; I’ve never liked the vibe of sunning wearing almost nothing next to a bunch of fully clothed people eating lunch. Unfortunately this setup is common.
Usually there’s drink service and I just use that, then I’ll toss shorts on when I have to use the restroom or whatever. I’m not about to walk through the lobby or use an elevator in my thong.
Likewise I tend to look for places with ground level rooms where you can walk right out to your door to the beach/pool without going through a lobby or bar. Outdoor stairwells are fine too. Walking around in a swimsuit is more normalized in these arrangements.
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I never used it but I keep a mesh, split side shorts in the inventory. It’s see through if you’re naked so I keep my thong on underneath. It’s a sun through so I still work on my thong tan line.
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@BeachBossMode That pretty much sums it up for me: context! But sure glad that step one is well over with!