If you mention the words "vegetable gardening," the first thing many people think of is tomatoes. There are hundreds of different varieties and the most difficult part is trying to decide which variety to grow. Local plant suppliers should carry varieties that are suited to your area.
The "when to" part of growing tomatoes in Florida can be pretty tricky. In North Florida, tomatoes are planted in February after the last frost, so they will produce the most tomatoes before summer heat sets in. In Central Florida, tomatoes can generally be planted in early February for early summer tomatoes and again in September for picking tomatoes in fall and winter. Just remember, in early spring there is always the danger of frost, so be prepared to cover the plants if a frosty night is predicted. In South Florida, tomatoes are grown from August through March.
The easiest way to plant tomatoes is to buy already-growing transplants from your local garden center. Look for stocky, dark green plants with stems about pencil thick. Set plants deeply, covering the stem about 2 inches above the roots with soil. Tomatoes are thirsty and hungry plants, so be sure to water thoroughly as needed to supplement rainfall and feed with a tomato fertilizer such as Miracle-Gro Shake 'n Feed Tomato, Fruit and Vegetable Plant Food Plus Calcium. Staking or caging to provide plant support is typically required for most varieties.
Tomatoes should be left on the vine until they have turned fully red (or fully orange, yellow, or pink depending on the variety). Tomatoes will be more mouthwateringly delicious if picked when ripened on the plant. That's the beauty of growing tomatoes in your backyard versus buying in the grocery store, where they're picked before they're fully ripened.