Want to take GF on trip for her bday around October where would be best?

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I want to take her somewhere like Puerto Rico or the Virgin Islands where there is beaches and stuff, are these places nice to go to around the beginning of October?

Also where do I even start in planning such a trip? I’ve never really been outside of MD and don’t know anyone IRL who have (I know, pretty boring).

How much $ could I expect to waste if I want to go for 3-5 days?

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