re: 20 year anniversary trip

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We would honestly prefer somewhere in south Florida, or somewhere with a direct flight from New Orleans…

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Then I would just do that. Why do something when you'd rather do something else?

Fly into FLL and drive South. Stay a night in Ft Lauderdale, then stay a couple nights in Key Largo, then a couple in Islamorada, then a couple on Key West then do it in reverse with a couple nights in Marathon then a night or two in Miami then fly home.

Southwest has directs from MSY to FLL.