Florida strawberry growers frequently relay-crop (RC) vegetables with strawberry to offset high input costs. Relay-cropping consists of planting two crops at different times on the same raised bed which helps growers' lower risk due to diversification and maximize economic returns. Four separate experiments on relay cropping strawberry with jalapeño pepper and cantaloupe were conducted at Balm, Florida, in 2016-17 and 2017-18. The objective was to a) determine the effects of relay-cropping on crop yields, b) optimize pepper and cantaloupe planting date, and c) optimize the strawberry termination date when relay cropping with vegetables. Strawberry yields were unaffected by the presence of vegetables. Pepper yields were unaffected by the presence of strawberries, but cantaloupes yields were significantly (p = 0.0250) lower when planted with strawberry. Early January to early-February were the optimum dates to transplant pepper with strawberries transplanted in October but date of planting did not affect cantaloupe yield. Early January to early-February transplant dates for pepper resulted in net profits of around $23000-38000/ha in 2016-17 compared to the baseline treatment (strawberries alone). However, in 2017-18 all of the planting dates of pepper with strawberry except January 4 resulted in losses of $2000-18000/ha. In 2016-17, cantaloupes planted in late January and early February resulted in profits of $2986.3 and 2705.1/ha, respectively. All other planting dates resulted in loses compared to baseline treatment. In 2017-18, all the planting dates resulted in net profits of around $6700-14500/ha. In conclusion, cantaloupe and jalapeño pepper can be relay cropped with strawberry with no negative effects on strawberry yield. However, early planting dates tend to maximize economic return.