Where to spend the winter months?

[+ SundayZip]

My question is a twist on the "Where to retire?" thread from @MidwestCoastal. I really enjoy the progressive, midwestern city where I've lived for the last 40+ years and have little desire to permanently move. But like many others, I'd love to go someplace warmer during our cold winters. So my question is, where is a good place to spend the winter months? Once I narrow options to a short list, I'll probably visit a few places and then do a trial rental at the top contender. Of course Ft Lauderdale and Palm Springs are the obvious choices, but there's got to lots of other good options. I'm open to anywhere in the US, Mexico, Central America and South America. Here are a few things that I'm looking for:

 

- Liberal

- A supportive gay community

- In or near a reasonably sized city. I'd go crazy in a rural setting.

- Fairy easy access to an airport (I may decide to travel during the winter months).

- I'm fluent only in English but I could learn to get by in a Spanish speaking country (or I'd be eager to try).

 

Suggestions?

[+ not2rowdy]

Sounds like you seek to join the snowbird flock.

Here are some links to maybe narrow the field:

 

Domestic:

https://www.tripping.com/guests/cheapest-snowbird-destinations

https://www.snowbirdadvisor.ca/best-us-destinations-for-canadian-snowbirds

https://viewfinder.expedia.com/20-best-places-snowbirds-winter/

 

International:

https://www.tripping.com/guests/10-best-non-us-destinations-for-snowbirds

https://www.snowbirdadvisor.ca/top-international-destinations-canadian-snowbirds

https://money.usnews.com/money/blogs/on-retirement/2011/11/14/the-6-best-places-to-be-a-snowbird

[+ Charlie]

Winter in Chicago is summer in Australia and New Zealand.