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Crazy to go in October or November?

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My husband is military, and with that, we are able to travel to Iceland on a military flight for free. We are beginning to tentatively plan a trip overseas anywhere from mid-late September through Mid-November.

That said, Iceland is a desirable destination for us. Would we be crazy to travel there during that timeframe?

In addition to weather concerns, are there any major holidays we should avoid (business closures, throngs of people, etc) or just general advice as to why we should consider going elsewhere?

Thank you in advance!

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