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Ah, wish I'd seen this earlier. I've hitchhiked almost the entire country at this point. I had a working holiday visa last year and didn't bother working, instead just hitchhiked around.

I guess you already have tickets to Tokyo, but my number one advice would be to get the hell away from Tokyo. I'm actually surprised to here the other guy had an easyish time hitching around the Tokyo area because from what I've heard it sounds unreasonably difficult. I've personally never bothered because I just plain don't like that area much.

So yeah, number one tip is get out of that area, then everything becomes a million times easier. Hokkaido is a hitchhiker's paradise, but it's a bit far depending on how long you're here for. You can find flights up to there for about a hundred bucks, which isn't too bad. Or again, if you've got a decent amount of time, just hitchhike up towards Aomori and take the ferry.

Recently over Golden Week I hitchhiked from Aomori Prefecture, the northernmost prefecture on Honshuu, the main island, to Kanazawa in Ishikawa prefecture, which is about 850km away I would say. That was a really pretty route. I liked it a lot.

You mention the expressway, and I'm curious as to what you mean. Like, paid expressways? If that's the case, just know that getting on those in the first place is actually pretty difficult. I've done it a couple times, but only once was I able to actually hitchhike from in front of an interchange and onto the expressway. Hitchhiking on the expressway or too close to the on ramp to the expressway is illegal. Once on an expressway, hitchhiking from parking/service area to service area is very easy and fast, but is a very lousy way to see the country. The sound barriers completely remove the very beautiful scenery from the equation. That being said, on my way back from Ishikawa Prefecture during Golden Week, I covered about 1000km in one day coming back home to catch work the next day (there was a detour into Tohoku region, so 850km became closer to 1000km). But again, you see literally nothing and it's too fast to actually be interesting at all. I much more recommend taking the national highways because they're beautiful, often running by the sea, and people are a lot more willing to stop there than in front of a on-ramp (though I guess once you're already in a PA/SA, it's about even).

As for maps, use Google Maps. It doesn't get any better than that. As soon as you get here, go to a huge tech store like Yodobashi Camera and pick yourself up a prepaid sim for your phone (obviously phone has to be unlocked) and use maps. Alternatively you can get one of those portable wi-fi things but I never did because there's no such thing as a cheap one as far as I've seen.

If you have quite a bit of time to mentally prepare before the trip itself, I highly recommend reading Hitching Rides with the Buddha for stories:
http://www.amazon.com/Hitching-Rides-Buddha-Will-Ferguson/dp/1841957852/
And his practical how-to book Hitchhiker's Guide to Japan:
http://www.amazon.com/Hitchhikers-Guide-Japan-Will-Ferguson/dp/0804820686/
The guide is incredibly outdated in terms of destination information (worst was getting to an area with an amazing sounding hot water waterfall that led to a free open air mixed gender onsen, only to find a landslide closed the whole thing down like 8 years ago) but the route information is solid, granted it is more focused on Hokkaido, Tohoku region, Kyushu and Shikoku, with almost no focus on central Japan (Tokyo, Osaka, northern Kanto, etc.)

If you have any other questions about hitchhiking here in Japan let me know. I'm not an expert, but I do know a shit tons after a year of doing it.

Hey, I did a 17-day cross-country trip a while back spending virtually no money. I wrote a book about it that contains lots of advice about hitchhiking and sleeping across America, but I'll summarize the gear advice below:

-carabiners

-one pair of great walking shoes

-two pairs of pants

-three shirts

-one jacket/sweatshirt

-four pairs of underwear

-four pairs of socks

-one belt

-gloves (optional)

-hat

-sunglasses (optional)

-sunscreen

-tent / bivy sack

-sleeping bag

-at least two days worth of food

-big water jug, with reinforced bottom

-lighter (even if you don't smoke)

-portable phone battery (and phone and charger, maybe a car adapter too)

-headphones!

-umbrella

-fat chisel tip Sharpie

-basic first aid stuff

-knife

-pepper spray

-ibuprofin/acetominophen (optional)

-a few feet of rope

-a bandana

-a small paperback book (maybe a small blank book for journaling)

-toothbrush and toothpaste

-wallet

-earplugs (you'll thank me later)

-insect repellent (optional)

40 liters is a fine size, if you clip a few things to the outside with carabiners. For the life of me, I don't understand why people bring cooking stoves around with them. They're far too heavy, and their utility is limited and situational, and completely extraneous. You can eat raw or precooked food, or sometimes make fires to cook stuff. Even when I lived in my car for a month in the Rocky Mountains, I never once wished that I'd brought a portable stove with me.

The ukulele is good, but if you don't already know how to play, you shouldn't bother. Bring something small like an Irish tin whistle/flute or harmonica. I brought my harmonica on the road with me, but I didn't get more than an hour of playtime in 17 days on the road.

I don't want to sound like someone trying to plug my book, but Hitchhike America contains all sorts of advice and stories for a first-time hitchhiker, especially one in the United States. There is a section after the main narrative dedicated to hitchhiking tips and tricks as well as about ten blank pages for journaling. Also there's a blank map of the continental United States for mapping out your general route (no roads though). The paperback edition was released less than a week ago!

Simply ask people you meet if they know anyone who needs some chores done for cash.
Chores tells people that you are looking for short term stuff. Cash tells them you want informal work.

Use Craigslist gigs to find one day events and quick jobs.

Think about what you have done in the past and things you enjoy doing. How can you use that to make money? Can you play musical instruments, draw, tell jokes, sing, do street magic, make jewelry, crafts?

Do you have any skills? People who can fix things always have plenty of work.

Computer skills will allow you to work anywhere you have a good internet connection. Codecademy.com can teach you programming, web design. /r/digitalnomad

Sign up with all of the national temporary employment agencies. Take all the short assignments. Then when you move to a new city ask them to forward your information to the new city.

Keep a set of clothes just for catering jobs. Black slacks and white shirt. They feed you, pay well and send you home with left overs. Call all the catering outfits in an area and fill out an application if needed.

If you have a tarp and a compact compressible sleeping bag, you can sleep anywhere there are weeds tall enough to conceal you from view. Join couchsurfing.com and other hospitality exchange sites and fill out the profile, upload several pictures of yourself. Look for couch surfing events and attend. Friend people you meet there and write reviews for them. Ask them to do so for you. Contact hostels and offer to work in exchange for a room. You should never have to pay for a place to stay.

Coolworks.com has many job offerings that include accommodations and food for employees.

Carry a means to cook simple food. Gas canister stoves are very cheap and canisters are sold at Walmart for ~$5. A stainless steel cup or a stainless steel dog bowl without rubber feet from dollar tree will let you boil water or heat food. Use aluminum foil for a lid to save fuel. Use a cardboard and foil wind screen with any stove and boil time will be shorter. Fire restrictions in the west prohibit other kinds of stoves. Cat food can alcohol stoves and wood burning beer can stoves are free alternatives but not in California. Use a clean 5 hour energy bottle to collect alcohol based hand sanitizer from toilets for fuel. Use another 5 hour energy bottle to collect non foam soap from restrooms. If you are camping, don’t cook or eat where you sleep. Cook in a park and go to a different area to sleep. Critters smell food and come around to investigate. A dog or raccoon can be annoying but a bear may force you to launder your underwear.

Since you don’t have to spend money on accommodations and food will be free or cheap your need for money will be very little. Avoid addictive behaviors like a plague. Drugs, alcohol, pornography, gambling, tobacco, indiscriminate sex and prostitution will drain your finances dry in a amazingly short time.

Study how to acquire food without using your own money. Hit a library or used book store and look for books on wild edible/medicinal plants, herbs and mushrooms. Foraging, ethnobotany, entomophagy, bush tucker and wild crafting are fun hobbies in themselves. Hunting, fishing, frog gigging, crawdads, clams, mussels, seaweed, berry picking and gathering nuts. Make sure to follow the law of the state you are in and get a license if one is required. Try road kill. Ask at any farmer’s house if you can trade some labor for some food. I never met a starving farmer.

I don't know if you've got the space or care to carry the weight, but you might want to look into carrying a compact bike rack. I don't use this for hitchhiking but I have used it to carry my bike many miles on the interstate. That'd definitely open up your options if people are willing.

This is one I've had for about a year now. it's about 6-7 lbs and can fold into a backpack

https://www.amazon.com/Allen-Sports-Compact-Folding-1-Bike/dp/B004C94X12/ref=sr_1_5?ie=UTF8&qid=1493706872&sr=8-5&keywords=folding+bike+rack

I always swore by a real small tent but this year I'm leaving with a Geertop bivvy tent. Enough room to keep your pack inside with ya, small enough that you can be a little more stealthy if needed.

https://www.amazon.ca/GEERTOP-1-Person-Lightweight-Backpacking-Aluminum/dp/B01N1TCYOW/ref=sr_1_8?ie=UTF8&qid=1500949497&sr=8-8&keywords=geertop

oh and also, it depends on the sleeping mat... Personally I would be a mess without it but one of my good buddies just slept on his extra clothes he had in his pack. Depends on your comfort threshold I guess but I'd say just get one... it'll mean the world to you after a long day on the road.

Back in the 1990's I hitchhiked all over the U.S., Mexico, the Bahamas and Venezuela. I lived on the road for four years and wrote a book about it. There is a LOT of info in there, that although from 20 years ago, would mostly be relevant today. It's free on Amazon Kindle until July 5th. https://www.amazon.com/Travels-Road-Dog-Hitchhiking-Americas-ebook/dp/B01E6KGXBY/ref=sr_1_1?s=digital-text&ie=UTF8&qid=1498975283&sr=1-1&keywords=travels+with+a+road+dog

The camping gear is where things get murky. On the one hand, I have sufficient equipment for the conditions, but there's a weight/bulk issue. This is my tent it weighs next to nothing and is a cinch to attach to the backpack, even with a tarp included. As for sleeping bag/bed roll, that's where I'm having difficulty making a decision. My sleeping bag which is only rated for about 30-40 degrees F, or this combined with a blanket that is essentially two canvas sheets sewn together without filling. The fleece and canvas blanket are a little bit lighter but much less bulky, than the army bag, however, there may be times when I really wish I had the army bag. I also have a mylar blanket.

Not bad, I know if I was always staying in accommodation I could fit everything I need into a 4L cross body bag.

https://www.amazon.com/gp/product/B01MFG454H/ref=ox_sc_saved_title_10?smid=ATVPDKIKX0DER&psc=1

A Grease Pot works just fine, light and cheap.

This road atlas, 100' of parachute cord, Utility knife, The clothes on my back.

Beyond that, it all depends on how far I'm going, where I'm going, and the time of year.

Here is the mobile version of your link