When to plant Winter squash in Florida
In fall, from June 20 – July 20 in Crestview to Aug 1 – Sept 1 in Pensacola.
USDA's earliest safe spring and latest safe fall planting dates, matched to each place's average frost dates.
Planting dates: USDA Home and Garden Bulletin No. 9 (1967), tables 4 and 5. Frost dates: NOAA U.S. Climate Normals 1991–2020. “—” means the place's frost date is outside the table. The full USDA table for winter squash.