WWYD, girls weekend edition

Anonymous
Trying to plan an annual getaway with girlfriends. This year has been really tricky navigating everyone's logistic requirements, but have landed on either Naples FL or Chicago. (Random I know, but like I said: logistics.) We all live in various parts of the South so the heat won't be an issue. Will be going 5 nights in July, first and last day will mostly be travel for the group.
Anonymous
Anonymous wrote:Trying to plan an annual getaway with girlfriends. This year has been really tricky navigating everyone's logistic requirements, but have landed on either Naples FL or Chicago. (Random I know, but like I said: logistics.) We all live in various parts of the South so the heat won't be an issue. Will be going 5 nights in July, first and last day will mostly be travel for the group.


Is there a question in there somewhere or did you mean to post this nonsense?
Anonymous
Either could work but think about the difficult personalities in the group and what they will likely complain about. I'd even make two sample itineraries and see which one would be most relaxing and encourage social time versus rushing around. If most are foodies, pick Chicago.
Anonymous
Do people want to relax (Naples) or go out and about (Chicago)?
Anonymous
How hot will it be in Florida in July?
Anonymous
Anonymous wrote:Do people want to relax (Naples) or go out and about (Chicago)?


This is the core decision to be made. Some accommodation can be made in either place (e.g. a spa morning at a fancy hotel in Chicago or an extravagant meal out on the main strip in Naples), but the core of the trip will be different based on these locations. Let the group vote and go with the more popular desired mood for the trip. If it's not an overwhelming win in one direction, make sure that there are some of the "other" types of activities either built into an itinerary or at least available as options.
Anonymous
Much better food in Chicago! And big ole gag to florida in july lol.
Anonymous
Big ole gag to Fl in general, and 5 nights is way to long for a weekend.
Anonymous
This would totally depend on the personality of the friend group I'm going with.

Some friends love to "go, go, go" on a girls' trip and do a lot of activities. In this case, I'd pick Chicago.

Other friend groups are more chill and are happy to hang around the pool and just chat, in this case I'd rent a nice condo in Naples.
Anonymous
If you don't plan on mostly drinking/swimming, choose Chicago, more to do. It's not going to be cold there either, you know, it can be pretty sweltering in July.
Anonymous
Chicago is so fun in summer.
Anonymous
I went to Chicago for a summer girls weekend and it was great. We took an architecture boat tour, walked around a bunch, ate at lots of good restaurants. Much easier to split up occasionally when you can walk or take the El everywhere vs needing to drive in Florida.
Anonymous
You can go to the beach in Chicago in the summer too!
Anonymous
I live in Chicago and this is the best time of the year in the city. Everyone will be out and about - you can relax or go out, the choice is yours.
Anonymous
Five days seems long!
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