The list
Less dependent on season and location:
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I love mandarins and other small oranges because they are easy to peel and don't need to be washed. Ideal on the go fruit. I've found that when buying lunch at a deli/supermarket two mandarins will be as filling as chips for less money, while being healthier.
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Pink lady apples, as well as whatever other local varieties you might have, are great. Smell the stem and butt to get a sense of flavor and ripeness. Fiji are good in a pinch. Apples are the perfect modern gmo fruit, as good from a supermarket as they are off the tree. Strain matters more than ripeness/freshness. Durable, last for a long time, especially in the fridge.
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Dates are not only delicious but the best way to keep your blood sugar up before a workout. Medjool and Deglet are my favorites.
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Grapes are wonderful, especially when chilled. There are a lot more varieties than people think, some that are more tart or sweet. I have never met a grape I didn't like. Concords are great for Jams as well as just for something different. Any old grape will do just fine though.
More dependent on season and location:
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Watermelon are the most refreshing thing known to man.
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Strawberries raspberries and blueberries fall into the, "delicious but too expensive for me to actually ever buy them." If you can afford them or find them on sale/for cheap go for it.
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Papaya are delectable and substantial. Odd smell that bothers some, but will go away after a while of eating them/being exposed to them.
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Mangoes are probably more delicious than anything human will ever make on our own, my second favorite fruit.
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Pineapples are freaking great, and super cheap frozen. My favorite smoothie fruit.
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Plums/pluots are delicious when in season. pluots are similar in taste, perhaps not as perfect when 100% ripe, but much more durable and reliable.
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Apricots, wonderful fruit that make my favorite type of jam.
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Pears have all the refreshing finish of a grape with the substantial feeling of an apple. Divine texture when ripe. Don't buy the brown ones though, I have never understood why they exist.
Entirely dependent on season and location:
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Guava, hard to find outside the tropics but make for my favorite flavor of fruit drinks. Buy POG (passion/orange/guava) juice if you see it.
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Passion fruit, Delicious and perfect for topping a desert with. Very tart but not as much as a lemon.
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I love blackberries but unless you are going to bake/jam them you need to go to a farmers market or pick them yourself. The ones from the store pale in comparison to the fresher stuff. Blackberry vines ripen super unevenly, so they are hard to pick en masse. I had a lot of blackberry vines near where I grew up, they were absolutely delicious, but would ripen over the course of a few months, even berries right next to each other, rather than all at once.
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Peaches! Very sweet, their puree makes for wonderful cocktails
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Lychees/momones/whatever other similar fruit. A large seed coated in a clear fruit flesh inside a neat red amoeba thing. Crack it open, chew around the seed, then spit it out. Super tasty. Sorta like a pineapple without the tang, but with a grape's/watermelon's refreshing finish.
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Mangosteens are the tastiest fruit I've ever had the pleasure of meeting. Absurdly delicious. Unless you're near where they are grown, avoid them. They don't travel or keep well. You might find mangosteen drinks in Asian markets. Its been a long time since I had one but I remember them being roughly halfway between a lychee and a strawberry, with some orange and mango notes as well.
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Persimmon are the sweetest fruit on this list, even sweeter than dates or peaches. They can only be found in a roughly 3-month period, but are delicious when ripe. Only eat them if they are barely holding together. Scoop the flesh out with a spoon and avoid eating the skin, mildly toxic. They are also super environmentally friendly. Very drought tolerant, need little fertilizer, perrenial, and are great at holding back desertification.
Fruits that others like that I don't: Dragon fruit, star fruit, grapefruit, gooseberry, marionberry. Pomegranate and kiwi are nice but too annoying to eat for my liking
I love fruit dearly. They would comprise most of my diet if I could afford it.
Note that I'm an American; so if you're in the tropics finding good lychees will be as easy as finding good grapes, while finding good grapes will be extremely hard, good stone fruit almost impossible, and good blackberries actually impossible.
The fertilizers and water are a much bigger climactic impact than transportation. Based on what I've learned its more environmental to ship food from far away where it grows easily than to grow them in areas where its more difficult. A farmer growing rice in vietnam will use way less water than one in California, while pineapples from the tropics create a much greater volume of fruit with less fertalizer, I think, than berries grown in temparate conditions. Favoring perennials is a great point though, and so is buying from farmers markets. Most farmers selling at markets using much more sustainable practices than those selling to supermarkets. This is because the more sustainable practices lead to better taste.