Masses of cruising sailboats arrive in South Florida during the Dec-Jan period. Larger boats "ride" northers down from St. Simons to Canaveral...that''s done well west of the gulfstream. Then it''s an easy shot outside to Ft.Pierce. After Ft. Pierce it can be day hops outside (and against the edge of the stream)or the ICW with lots of bridges down to Miami. You can make Miami in 4 winter days from Canaveral if taking the ICW all the way.