First impression: those window box planters are not at all ideal for peppers and tomatoes and you have way overcrowded them. Each plant needs its own pot, round is better, at least five gallon for the peppers and at least 10 for the tomatoes. The cucumber would also benefit from larger pot of its own. Bigger is preferable so they don't dry out too fast and it makes less work for you. Here's a quick guide to round container widths and their corresponding trade size:

12" pot = 5 gallon

14" pot = 7 gallon

16" pot = 10 gallon

18" pot = 15 gallon

20" pot = 20 gallon

24" pot = 25 gallon

30" pot = 30 gallon

I say "trade size" rather than volume because trade size doesn't equate 1:1 with the actual volume of the pot. For example, 5 gallon pots typically have an actual volume of a little less than 4 gallons. And you should fill the pots right up to 1/2 inch below the top with either potting soil or potting mix, not garden soil.

If you feel like like poking around the forums there is a lot if good information on the container gardening forum, the vegetable gardening forum, the growing tomatoes forum, and the hot peppers forum. But the container forum would probably be the most relevant for you.

The herbs will do fine as long as you don't over water them, but you'll have to figure out how that works because I hear Florida gets kind of hot during the summer. And each herb has it's own water preferences.

Your doing great keep experimenting, if your allowed to, consider some hanging baskets to maximize space.

Your plant selection is wise. I did not plant a cherry tomatoe this year and I miss them bad. Great snacks.