What to plant?

I am building/rebuilding  some 55 gallon sub irrigated planters.
What should I  plant?
I'm wide open for ideas.
Right now I have about 5 sub irrigated planters dedicated to tomatoes.
My family eats berries,  but not  most vegetables.
I have one blueberry barrel, and I will add at least one more, but I will need more  peat for that.
The first barrels will have some peat,  but not 100%.
Here are some photos that show what we are dealing with :

Are you trying to appeal to the non vegetable eaters? If so, I would consider ground cherries, sun berries, and melons. Yum! Like annual berries, and the ground cherries can even be stored for a while and just get sweeter.

Otherwise cucumbers and zucchini would be my choice, then peppers.

Good ideas!
We did grow ground cherries and sun berries, but we didn't care for the taste of either.
My family likes some  melons and loves cucumbers, but will I have room for them in a barrel?
I have never gotten much fruit from either plant but I always seems to get huge leaves and vines.
I've been told my soil has too much nitrogen, even though I use only compost for fertilizer.

I guess I could go vertical with a trellis.
Would the cumbers/melons climb on their own or they need to be trained?

Bell peppers are welcome in the family, at least the red, orange and yellow ones.
I suspect they will be displacing some of the tomatoes from their pots.

Do you put anything in the soil to wick moisture up? Or does it not need anything? Perhaps something with deep roots would help bring moisture up.

What about winter squash? This is the year for it I think,  with all the economic uncertainty. If you're worried about the containers being too small you can plant bush varieties

Justin,  the soil I added on top of the peat was old potting soil, which was about 50% peat when it was new.
It's old now and mixed with added compost but I'm hoping it still has wicking umpf left in it.
I generally leave my wicking soil in place and add rabbit poop/litter as a top dressing.
That and being used as a dump for yard sweepings did change the original soil.
The sifting removed a lot of rock's and wood chunks.

I just came home from work in the middle of writing this, and stopped to squeeze a handful of said soil-its very fluffy,  hard to get it to stick together even though it's moist.

I wish coconut coir wasn't so expensive as compared to peat.
I did try wood pellets once,  instead of peat , but that was a bust.
Now that I'm making a fair bit of charcoal, maybe I'll try biochar as my wicking material.
If it works,  it should last forever in that role.

Back to plant choices,  I have grapevine that is in another barrel right now.
That barrel is really heavy but it needs to be moved and I'm not as strong (or foolish)  as I  once was.
I think this grape vine could take being transplanted just fine, and if it falters,  well it's easily replaced from cuttings.
When I looked into companions for it,  most of the ones mentioned  are herbs that prefer things dry, or nitrogen fixers,  which I don't really need, I already get too many grape leaves as things stand.

If I do choose the grape vine,  maybe a big leafed pot green would be a good neighbor

James,  I has no idea there was such a thing as bush or semi bush winter squash!
After a little reading,  I'm convinced I want some bush/semi-bush butternuts for the raised beds at my second yard.
I think even these toned downed squash would get too  big for a barrel,  though a kiddy pool or the top off an IBC tote would make for a right sized container.

I was just thinking I've never done carrots before,  but this barrel has over a foot deep of fluffy soil...

The size of the infrastructure (55gallons)has me leaning towards bushy perennials that benefit from rich, moist, well-drained soil.
Because 55gallons is relatively roomy,  but not infinite the ability to thrive in the face of aggressive pruning would be good as well.

Thus grapes,  for example.
A fig might like a sub irrigated planter as well.
Maybe another variety of raspberries.
There will be at least three ,  if not 4 or 5, of these new barrels to plant,  so keep the ideas coming!

in that size barrel i think you could plant anything.

cucumbers will definitely work, i got great yields for asian cucumbers in 20 liter containers earlier this year (one plant per container). I plant containers under my carport, cukes in the summer and tomatoes in the fall, and they go bananas. The cukes climbed just fine, I needed to keep on top of them at the beginning but they were just gorgeous.
I might also try sweet potatoes, if you have some peat to make fluff. (yes, not a fruit, but it makes pie, so it sort of counts as fruit)

Edited to add- loofah might be fun. Practical (replace your plastic sponges) and they grow well (they take a long time to get started, don't be surprised).
I think melon could work. Maybe some basil alongside it to go with your tomatoes and cucumbers?
Also, how about goji berry? I have been trying them forever with no luck, but I think they like good drainage.