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I should say I haven't ever done anything very outdoorsy, but I would like to make sleeping outdoors a part of the bicycle touring which I hope to do. But a worry for me is that I have always had problems getting proper sleep even indoors, and I want to make sure that I maintain a healthy lifestyle.

Personally I am very easily distracted by the breeze and by outdoor noise or the general openness (whenever I try to read a book in the park). What is your experience? Would a tent or tarp be better for being closed vs open? Earbuds? Would animal noises be able to wake you up in the night? Is it possible to sleep properly in heavy rain?

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If you've never slept in the open before, you'd probably be happier in a tent than a tarp. You can always move your sleeping bag out of the tent and sleep under the stars if you find you like it. Also, note that a tarp doesn't give any privacy, nor will it be of much use in a heavy rain. – ab2 Mar 17 at 2:14
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I have to add I'm suffering from an atention deficit and know what you are suspecting and would probably confirm it with one exception. Heavy rain is the best thing. I really enjoy the sound of it. it is an continious noise that drows any other noise but is so continious that it doesn't give any distracting noises, so at least for me this is a good thing. – Zaibis Mar 17 at 9:37
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I posit that if you can't sleep, you aren't tired enough and you need to be biking harder. – Phil Frost Mar 17 at 14:07
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Frankly, if you do proper outdoorsy stuff during the entire day you should be tired enough in the evening to sleep like a baby. ;) – fgysin Mar 17 at 14:09
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I sleep FAR better outdoors than indoors. I sleep in a warm sleeping bag in a tent. – gerrit Mar 17 at 14:38
up vote 25 down vote accepted

Quality of sleep can depend on a multitude of factors. These are some of my experiences:

Quality and appropriateness of gear

Most people sleep poorly if they get too cold or too hot. Having a quality sleeping bag that is appropriate for your climate and time of year will definitely increase the likelihood that you will get quality sleep. Material matters when it comes to sleeping bags. Down will regulate temperature better, but is useless when it gets wet. Synthetic materials are poor at regulating temperature, but keep you warm even when they get wet. Don't buy cotton.

Having a sleeping pad will contribute to a good night's rest. The ground acts as a heat sink, especially when your sleeping spot is on sand or rock. Forrest duff will act as an insulator, and I will go lighter on the sleeping pad if I know in advance that I will be staying below the timber line. When it comes to sleeping pads, you have a choice between air mattresses and foam pads. The former can be a bit noisier and obviously can be susceptible to leaks, but, in general, is lighter and more comfortable. The latter is cheaper, and can withstand a beating.

Some people sleep best in a tent. Some people sleep best under the open sky, or as close to it as possible. In the summer, I often just bring a tarp in case it rains, since I have a hard time getting up in time if I sleep inside a tent. Tents (or insect nets) are a major plus when setting up camp next to mosquito-infested waters.

Maintenance of gear

If you get wet you will sleep poorly. Make sure you keep your sleeping gear dry. I keep my sleeping bag in a dry-bag to prevent it from getting wet.

Experience

For a couple of years, I have led wilderness trips for children. I have observed a correlation between children who spend time outdoors on a regular basis and getting better night's rest. I suspect this might have to do with being in an unfamiliar environment. On longer trips, most children were sleeping well at the end, probably due to exhaustion and a new-found familiarity with the outdoors.

The human factor

I find that the single most annoying thing for myself when trying to fall asleep in the outdoors are inconsiderate individuals in close proximity. European campgrounds can be very dense, especially during the peak season, and often, at least, one group of individuals does not respect the quiet hours. For that reason, I avoid proximity to others whenever possible. I have a pair of noise-cancelling headphones that I use (they don't have to be plugged into anything) when I find myself in a situation like that. For me, it also helps if I can be next to a source of white-noise, like a creek. When going backpacking, especially in areas where you have some choice when it comes to campsite selection, the "human factor" can often be completely avoided. I have been on many trips in the mountains of California's Sierra Nevada where I had the nights completely to myself.

Environmental factors

Many people sleep poorly at elevation. What the elevation is that makes people sleep poorly varies heavily from person to person. In my experience, the slower you gain elevation, the better you will acclimatized, and your sleep quality improves.

I find that heavy rain does not distract me unless I am worried that my stuff could get wet. It helps with "the human factor" as well since people generally won't stay up as late in poor weather. It also provides white noise, which helps me sleep.

The elements pretty much tie back to the appropriateness and quality of gear. If I trust that my gear will withstand the situation, I normally sleep soundly.

The sun can be a factor as well. If you would like to sleep in during the summer months, make sure that you set up in a shady spot. There is nothing worse that waking up in your sleeping bag inside a tent that has been baking for 30 minutes.

The unavoidable

I have observed (on myself and others) that often the first night can be rough, even with good gear and a lot of experience.

Your general disposition. If you have trouble sleeping at home, you will probably find the same to be true in the outdoors. If your sleeplessness is due to stress, though, a couple of nights in the outdoors may help wonders.

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"make sure that you set up in a shady spot"...that's shady in the morning, not necessarily in the evening! – Michael Hampton Mar 17 at 6:16
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The human factor: I mostly wild camp now. Once you've slept on your own on a deserted mountain side with zero noise, camp sites are totally ruined.. – Liam Mar 17 at 8:34
    
the first night can be rough: me too, even if the new bed is in a luxury hotel - just because it is not familiar. The fresh air, exercise from riding the bike, and tiredness from lack of sleep should correct that soon on subsequent nights :-) – fr13d Mar 17 at 10:24
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nose-cancelling ;) (can't fix single character typo) – Ghanima Mar 18 at 9:45
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@Ghanima also helps with the stench of those campers that decide that soap is too civilized for their outdoors experience. – Mindwin Mar 18 at 14:06

I thing this is too broad and too personal to get a definitive answer.

Mine is: go try out for yourself as much as you can in a safe environment.

Experiment with different setups as much as you can: tarp vs tent, foam mat vs inflatable, try several sleeping bags if you can borrow them, or just buy and eventually resell them as I did.

If you have a garden, go sleep in it. I don't, so I spent several nights on my balcony in town, by using a thermometer to measure the temperature outside and record my feelings in the morning. My purpose was to test in practice what setups could keep me warm at what temperatures [this also includes going to bed properly feed and hydrated]. Also, I experimented peeing in a pee bottle (that is, a bottle with a wide opening) so not to need to leave the sleeping bag during the night to pee. That helped a lot. I also tried a bivy bag when it was raining, although not much rain was entering the balcony, I had quite a feel of it.

By sleeping on a garden (or, if you can't, on a balcony) you have a safe way to see in practice what you are going to feel later on and to get back in, onto your bed if anything goes wrong - like, you are too cold, you are too unconfortable, you installed your tarp poorly and it falls over your head, and so on.

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There isn't much to be said about the preparation that hasn't been said by DudeOnRock, but making sure that you are dry, have a comfortable sleeping pad, and are warm are definitely key. One thing to note is that you are going to be biking a lot, which will tire you out. I can tell you that some of my best sleep has been while camping, even when it was less comfortable sleeping arrangements.

Definitely sleep in a tent if you are worried about waking up and it's your first time outdoors, and make sure that you set it up properly. If not, water could get in when it rains (staking the tent out is key). If you want, feel free to bring earbuds if you like to listen to music when you fall asleep, or earplugs if that's what you prefer.

When setting up a tent, I would recommend putting a groundcloth/tarp on the ground, then your tent with a rainfly, then a space blanket, then your sleeping pad and finally your sleeping bag. The series of layers helps keep you dry if it rains, even if some part of your sleep system fails, or if there is a large amount of water. You would be more likely to wake up because you get wet than due to the sound of rain, which is why I think that setting up a tent well is very important.

One last thing is if you do intend to sleep outdoors, practice setting up and taking down your tent and sleeping arrangements at home first, that way you aren't trying to do it for the first time when it really matters. Tents are not necessarily intuitive, and experience with your equipment can help a lot.

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Well, it depends on you.

For example: When I was 16 years old, my parents moved into a small bedroom, and I got the "master bedroom" (the biggest bedroom of the house!). Why? Because in this 2 story house, the master bedroom was above the garage, towards the front of the house, and my father had troubles sleeping due to the sound of the occasional car driving by. I hardly ever noticed it (when awake). I am also quite capable of sleeping in many environments, having been known to sleep in airports and airplanes. Televisions aren't loud enough to keep me awake. I've also been known to wake up, and then fall right back to sleep easily.

So, the question is: are you like me, or like my dad? The core of my answer is that it depends on you; some people will be able to cope without much or any difficulty. For others, the identical night could result in the horrible experience of failing attempts to just get a little bit more sleep. It might be that you need to figure this out by just trying and seeing what the results are. Unfortunately, this "it depends on you" doesn't mean that it depends on decision that you can simply make; it may depend on factors that, as an adult, you're not going to be able to just easily change quickly just because you want it to.

Would animal noises be able to wake you up in the night?

You know, you may be able to figure this out at home. Try just leaving your windows open. Where I live, there are trees and I do occasionally hear the chirps coming out of the beaks of those small feathered flying things (though not most days).

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I borrowed a friend's tent/hammock. It is more of a bivy sack with ropes to hang it from two trees or anything else you happen to have lying around. You might also be able to get one that has a collapsible stand. It was comfortable once I got in, but it took a little doing to get in. You enter from the bottom on the one that I used. You might want to borrow or rent one to test it out. In fact whatever you do, thorough testing is a must.

My feeling though is that if you ride far enough, being able to sleep should not be an issue.

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Ask experts

Equipement recommendations for sleeping bag and underwear will be available in your outdoor store.

Sustain positive aptitude / attitude

Mental process is very important. Unfamilar noises and a freezing breeze ... embrace nature and do a psychological trick: Let the first night outdoor be one great night for a start. Really look forward to share a beer/whiskey with other bikers. Respect animal live! As pointed out in comments music should be adapted to animal life. Singing together also can be substituted by a nice talk in low voices. As well turn down music and listen to the rattling of the leaves - sound of nature is will become familar - a great night, the begnning of many calm nights.

The other answer provides a perfect overall recommendation and covers all areas of this answer.

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Don't play music too loud in the outdoors, please. It's not just annoying other people, it may harm the habitate of animals and even disturb their natural behaviour. – Wills Mar 17 at 16:10
    
@Willis, right. Distinguish between nature and a bike roadtrip on highway, in absence of mammel animal life. Correct behavior would make a nice question. I'll look it up, if already existing. – Stefan Bischof Mar 17 at 18:32

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