Newbie looking for sailing hours in the Carribean

[vangolfer]

Hey everyone, first-time poster here

I took sailing lessons (roughly 40 hours on the water) in my home base of Chicago this summer, and I think I've caught the sailing bug!

I work through the Internet, so I tend to avoid Chicago winters. I'd like to spend January somewhere in the Caribbean, getting some more hours sailing.

FIRST: I'm looking for a place that:

• I can sail
• Will have reliable internet
• Isn't expensive (furnished apartment for <$1,500/mo)

(I'm considering Cartagena, Colombia, as I already spent the past two winters in Colombia & am already relatively comfortable there.)

SECOND (and most important): I'm unfamiliar with sailing culture in The Caribbean (or, in general, for that matter), and have no idea how to get more time at the helm. I suspect some of you on the forum may have some suggestions. I hope to find a way to make regular shorter sails, and hopefully at least one overnight sail.

I look forward to any advice you might have. Thanks so much!