Hi Sundance,
Not sure how much value I can add here but I'll jump in.
Have you ever fished for Bonefish or Tarpon from a boat before? Don't want to insult you or anything if you're a veteran fly-fisherman, I just don't know. Three years ago, on my annual February trip to Cancun, I booked a guide for a day and went Tarpon fishing. Didn't catch anything. Saw a few. But what made it unpleasant for me is just the fact that I wasn't very comfortable casting 60' feet plus in a wind with one or two false casts. Time is of the essence with Tarpon as they are moving. I'm way more comfortable casting 30'. The experience was a little intimidating for me. Something to think about but I don't know your casting ability and comfort level.
Of the options you mention, I would probably rule out Mexico just because it's two people per boat. How would that work? Take turns when a fish is spotted?
I'm not saying I won't try hiring a guide and doing it again, but not for a while. I now fish from shore in Cancun right at the resorts and do ok.
If you decide and go for it, please let us know how you did.
Good luck.
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