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Jan 4, 2016 at 3:45 comment added phoog I would add that for the risk-averse traveler of means, it might be worthwhile to apply for a B-2 visa. The major benefit would be that you could lay out your entire itinerary in one go, to show that you aren't trying to game the system. Furthermore, B-2 status is not limited to 90 days per visit, further avoiding that perception. Thus, the already-small risk of being refused entry would be even smaller. The cost is $160 per application, though, so an order of magnitude larger than ESTA/VWP.
Jan 4, 2016 at 2:32 history answered DJClayworth CC BY-SA 3.0