Hi,

Im looking for information what side of Keys is better to sail from Miami (or Key Largo, not sure where is start) to Key West. What side is safer to me on 22 feet boat, Atlantic side or Florida Bay side? Thank you!

South of the Keys the Gulfstream can run pretty close to the reefs. That current runs east. The prevailing winds are easterlies. Not a very good situation for a 22 footer if the wind is up.
Inside requires vigilance, unless you like getting stuck in the mud or on a sand bar. Shouldn't be a problem with a good chart, but chances are you'll motor more than sail, at least to Marathon.

I still can change my plans. Is that better idea sail Naples to Key West? Will be there next week, wind is still blowing from east.

There is NOTHING between Key West and Marco Island just south of Naples. How long can you boondock on your Catalina 22?

Bigger boats are routinely lost on all three routes. That doesn't mean any of the routes are unsafe, but you'll need to know your capabilities, have proper water tankage, and the usual safety gear (VHF, flares, life jackets) along with being able to read the weather, which quickly changes or reverses this time of year. Filing a float plan and arranging to check in with someone on a regular basis is really not optional.

If you get stuck you pull the keel up. Boat will only draw 2' with the keel up.

And if you are still stuck, at least you can jump out and push her!

I do have Boat US, should be fine if stuck and can't move.

I have 2 - 3 weeks, Im flexible with time. Any sugestions?

I did some work before, keel pivot replacement, keel lift wire, all new rigging etc. Engine is 6hp Tohatsu 4 strokes and just come back from service. We have 2 VHS radios, GPS, Chart book, life jackets, 10 gal of gas, 7 foot ponton boat as dinghy with minkota electric motor. Anything else? I think will start on Biscayne Bay and head Key West thru Marathon.