I have a theory that's probably very unpopular. I believe that fruit is more often than not, bad for road trips and hiking. Don't get me wrong, I really like fruit, but it often gets a reputation for being the perfect road trip or travel snack, and frankly I disagree. I've decided to make a collection of common fruits, and give it a score based on how well I think it travels. I'll also give a short write up and justification about why I think it doesn't travel well.
Each fruit will get a score out of 10 1 being horrible for travel 10 being slightly inconvenient for travel. Keep in mind that this is an argument that all fruit is hard to travel either hiking or road trip, and no fruit is going to "win". The thing that I'm most excited about writing this is the fact that I get to eat all this fruit... for science.
Watermelon - 2 out of 10 - This is probably one of the worst fruits for traveling. If you want to keep watermelon in good shape, the best thing one can do is not cut it. I've kept watermelons in my fridge for over a month uncut and it still tastes great. However, after I cut into a watermelon it feels like you have at most a week before it starts to go. It's even more so if it's out of the fridge.
Let's also not forget about the trash left behind with a watermelon. This includes the rind and all the seeds. The seeds also create a problem as picking them out can make a mess. Even if you're some kind of watermelon seed ninja, in general watermelon is a fruit that requires a shower after eating it. This is not only a horrible road trip fruit, it's like the worst road trip fruit with one exception (see below).
Orange 5 out of 10 - The peel is the first and most obvious problem with bringing an orange on a road trip. If you happen to be driving the car, you'll have to pull over and peel the orange before you can even think about eating it. Even if we assume that you've pulled over and thrown away the peel, even if you're willing to lose that much time to get a little extra vitamin C. Then you have the stickiness.
Orange stickiness is no joke. There's two dose of sticky to contend with too. There's the obvious juice that you'll have to deal with when eating the orange, sure sometimes it's contained in the wedges, but that's pretty rare. Even if you have a lucky orange, you'll probably already be sticky because the peel releases a stealthy sticking liquid that I contend is worse than the juice on the inside. This ninja spray that comes off the peel is even a pain to wash off your hands, so you're probably looking at more wasted time scrubbing your hands at the next truck stop.
Banana - 6 out of 10 - Bananas are deceptive, because they may at first appear to be a great road trip or hiking snack. They're self contained in single serving packages and they taste great. But let's start off by looking at this self contained package. Banana peels have the ability to go brown and rot faster than any other fruit by-product. I feel like the banana peel starts to rot before you even finish the banana. If you're on a road trip your trash bag is going to smell like rotting banana very quickly. This is even worse if you're hiking and have no place to dispose of the peel. And don't go throwing that peel on the ground either, I've seen enough black and white comedy movies to know that's a lawsuit waiting to happen.
The other thing about bananas is the fact that they go bad really quickly too. Even if you leave the peel on, I feel like bananas have the ability to go from just ripe to a sock full of mush in minutes. And god forbid you happen to bump it in any kind of way. A bruised banana will be a sack full of liquid in no time.
Apple - 6 out of 10 - I think we can agree that the core of the apple is the worst thing about eating any fruit. Even in the perfect environment when you have a cutting board and knife, the core is going to be the biggest challenge you'll have with an apple. You have to make one of two choices when eating an apple, either go in deep and try to clean the core off running the risk of eating a seed or those sharp seed pods, or agree to waste some apple and leave a little extra room. No matter which you choose, you'll still have a core to deal with, and similar to the banana peel, the core of an apple rots at breakneck speeds.
There's also the juice problem. Some apples are very juicy and you'll find beads of juice running down your fingers for sure. Other types of apples may not bleed juice, but all apples will likely give you a light misting of sticky juice. Maybe a baby wipe or a stop at a roadside rest stop might help you, but I feel like that spray of stickiness will likely find a way to stick around.
Grapes - 7 out of 10 - I'm going to be honest, I think grapes might be the best fruit to bring on a road trip or hiking. They're not perfect, but I think they're as good as it gets. The thing is, there are very particular stipulations to make these an acceptable road trip fruit. First of all you have to get rid of the stems. This means that you have to break them into a bunch of very round and easy to lose pieces. If you have a container than you might be okay (but then you're carrying around an empty container all day).
If your grapes have seeds than consider the advise above null and void. I understand that seeds are the key to life when it comes to plants, but if there could be some way of outlawing seeds in grapes that are sold to the public as food I would not disagree. Seeds in grapes have been something that has made me sad many times.
Honorable Mentions - I just want to mention a few other of my favourite fruits that are also not great for travel. Dragon fruit is a terrifying looking fruit that actually might be one of the better road trip fruits. I've peeled a dragon fruit by hand and feel like you might be able to enjoy it while on a road trip. It'll likely be kind of messy, but not nearly as messy as the last fruit I want to mention, the mango.
Fresh mango is probably one of the most amazing fruits one can buy. If you live in a colder climate you might not understand what I'm talking about, but a quick visit to Pakistan or India will teach you how great this fruit can be. The problem is getting into it, particularly on the road or hiking trail. We once decided to pick up a mango while on a road trip in India. It was an amazing looking mango, super soft and ready to eat. The problem is we did not have a knife or cutting board to deal with it. We did some research and only came across warnings about how intensely messy it is to peel and eat a mango by hand. We ended up in the shower, in our underwear, covered in juice enjoying one of the tastiest fruits we'd ever eaten. In a car this would have been disastrous. Having said that, there are two fruits I can think of that are just no goes at all...
Pineapple and durian.
CC
Having said that who could not notice this pretty lady on the front of the bag, with the words pretty lady written on her. Now I’m not sure if "Pretty Lady" is the brand of grapes I’ve purchased or if it’s the variety. I’m not a grape expert beyond knowing that I like them in my mouth.
It’s a single grape with a light coating of white sugar. Sure to some it may not seem like that much but these little babies can go for as much as 300 Yen each (that’s about 3 American dollars). I had already searched Ginza for one of these before. Even better, I happened across an industrious sales person handing out free samples in the basement of a department store. The sample where only half of one, but I at least got to see what all the fuss was about.
As it turns out they’re not really that great at all. The grapes here are not as sweet as I’m used to in North America and the sugar only helps that out a little bit. I’d much rather just have a nice fresh bunch of grapes from home then pay the huge price here, but at least I got to try one. 
The problem was finding them in the little shops all over Ginza. I did find this cool Fujiya sign.
I also found this claw game filled with treats.
I found this store window with all kinds of treats in it; I think they’re marketing ladies clothes.
I searched through dozens of stores but couldn’t find the grapes. I’ll have to keep an eye open and hopefully find them later.
When I found this Popsicle with a picture of a guy completely insane about green grapes I had to give it a try.
Unfortunately the package was cooler than the treat. It was a little to fake for my liking. Having said that it’s not a big failure since in my opinion no treat could equal the taste and feeling of a mouth full of green grapes.