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The best thing to do is to apply for a B2 tourist visa before your H2B expires. That way, you do not need to leave the country before starting your tour of the US. Technically, you can leave and apply for a tourist visa in the Caribbean. Realistically, if your application is denied you will not be stuck in the Caribbean and unable to return to the US.

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Q: If your i94 h2b visa expires ie finished work in US can you fly to Caribbean and renew to tourist visa on entry to US then tour US?
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