Are you thinking 'coastal' & 'cross-Gulf' sailing?
Les, it isn't clear how far afield you would like to sail - and therefore, how much time you will require. In general, you face two different kinds of weather and sea conditions: a) for your winter & spring breaks, the 'clocking' (veering) frontal weather that are generated by Lows crossing N America to your north, and b) for your summer break, the potential for a tropical wave, storm or hurricane. There are of course also the issues of very different temps, both air and water, you will need to address in Dec and March.For local and coastal sailing, I would expect the passage planning process to be pretty typical. To research local/coastal conditions, you should have lots of options. Examples would be climatology & meterology reports published by regional Universities/colleges, NOAA reports & data, perhaps info generated by private f'casting businesses like Accuweather - probably far more info than you have time to read. There are also multiple regional cruising guides for the Gulf Coast that will offer weather synopses.For offshore cruising - crossing the Gulf and/or visiting the Yucatan - you might read the weather and passage planning sections of Nigel Calder's cruising guide for the Western Caribbean and/or his cruising guide for Cuba - they both discuss routing and weather issues for North Americans heading South, or returning. Also, Freya Rauscher's cruising guide to Mexico & Belize offers info on the passages from FL and the Gulf Coast (tho' I think it's less useful for your purposes than the first two). Also, don't overlook the influence of the Gulf Stream's offshoot ccw current in the Gulf, along with its eddies.The races from both St. Pete and Houston(?) to Isla Mujeres generate a lot of discussion each year in the regional sailing rags, and looking for info about them could prove quite useful. E.g. you will find the St. Pete race covered in Southwinds (http://southwindssailing.com/) which might also offer archived info on route planning & strategy that would prove helpful.You face a schedule squeeze re: visiting the Yucatan, whether big or little, depending on when your school calendar ends in the Spring. The Gulf has a history of generating both early- and late-season tropical storms, and you don't really want to be facing the prospect of doing a 4-5 day Gulf crossing much past early June, I wouldn't think...altho' some would feel a few more weeks is acceptable.Jack