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30th Bday Weekend Group Trip

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I'm looking for ideas of a city 3-day weekend get-away with 3-6 single and married females for my 30th birthday in October.
-I live in DC and would be planning with friends from Boston as well.
-I'd like to go to a place with a vibrant night life as well as some culture/walkable daytime activities (can include anything from music/shows, historic downtown, or beach, wineries, etc) to have fun at night, take it easy during the day with laid-back exploring.
-Budget of ~$500/per guest (I may try to foot the housing bill separately for the group if feasible, possibly find a house/apt to rent?).
-Have enjoyed New Orleans, Vegas, NYC, Austin in the past (all are still on the list-though don't know if Vegas is worth a repeat?). Considering Miami, Napa, CA and Charlottesville,VA (the last two for the wineries, not so sure about their nightlife).

Any other suggestions? Comments on my current list?

Thank you so much for any suggestions/comments! Trip planning is half the fun! :)

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