I live in Cape Coral in the winter time and do quite a lot of boating
when we are there. South West Florida is a wonderful cruising area for
houseboats since there is protected water both behind the islands in
the intercoastal waterway/Pine Island sound area, and also in the
Caloosahatchie River. Virtually all of the marinas on the river offer
protection from rough weather and there are numerous anchorages
available as well.

Some of or favorites are Tween Waters Inn and Marina on the bay side of
Captiva, the anchorage at Useppa Island across from Cabbage Key, and
Pelican Bay at the north end of Cayo Costa.

You need to get some of the better SWFL cuising guides such as
Clairborne Young's and do some studying since the possibilities are too
vast to cover in a quick note here.

Towing a dinghy should not be a problem. Best weather is usually
March, April and early May.