You backpacking and roadtrip types... how do you do it?
Is that something that happens in-between jobs? You take a long vacation? Quit one job, travel for as long as you can afford it, and then return and get another job?
It's something I've always wanted to do - but I guess I'm the type that would need it to be a little more organized. Not like a travel group with itineraries or anything, but like you said, with a few friends but otherwise a set number of days with known start and finish points, likely expense needs as well.
But organizing that kind of epic vacation with multiple people, who also take family and other vacations anyhow... difficult, in a word.
I'd have to admit to having too much trepidation regarding such - I'd be too worried about contingencies and the future and what happens if plans go south, like unable to have a job to return to or something. It's definitely outside of my comfort bubble.
With a planned vacation (alone or with a group), I could easily and gladly go hiking, say, along the Appalachian trail (doing things stateside, a little easier. cross-country trips would be far more enjoyable in Europe, far more costly) for maybe a quarter of it (likely less if alone, ideally more if with a group). I'm not one to willingly abandon my technology and comfort often (if not willingly, I'll fight and try to find every way to still get some technology time

), but for some time that, and even being forced to life off rations and on the ground and whatnot, is something I can tolerate. I've been forced to tolerate it for short bouts anyway (never deployed... yet), and doing it *because I want to* would change things entirely. I'd just love to escape, get away from everything, say fuck the world... until I return. Go on a journey, both physical and "spiritual" ("me time").
For that, whenever I can afford proper prep (good gear, rations/backpack food, etc) and have feel in the mood for exactly that, I'm definitely using vacation days to make that happen.
But extended backpacking adventures and whatnot? Like, just going months backpacking across Europe? I have no idea how I could make that happen at this point.
Immediately before, during, and after college... that was the time. If I was already in Europe it probably would have been a no brainer, as I did have the idea pop in my head more than once in those years.
I've let myself get too trapped in the system, man.
I'm too afraid of going without it. I fear there's no hope for me.
3) If you're going to be hitting up lots of big cities then you should buy an interrail or eurorail pass depending on your nationality.
If you're just going to hit up a few cities then look into Ryanair or just renting a car. Trains are kinda expensive but maybe a country rail pass would be reasonable. Case in point is me needing to get down to Frankfurt. Booking months in advance it would cost me $275 to get to Copenhagen and then an additional $275 to get to Frankfurt. One way. Compared to flying for $100 that makes no sense.
If you're going to hit up the countryside then just rent a car.
If you have more than 3 people then rent a car regardless if you can. The car will cost you roughly 20 Euro a day plus 800 Euro a month for fuel. It's less than 2000 Euro and if you use rail passes it will cost you more than that once you reach 3 people.
4) You can use google maps to plan out a route to start. If you're doing trains then I used to just print out a map with the main train routes and start plotting away. Take note of the time these trains take and try to plan out an itinerary. There might be good websites that can help you with this. If you're travelling by car then I would suggest using myscenicdrives.com. I am using it for my current trip and it's free for an unlimited number of stops and has great planning options. I've already created an awesome itinerary for my trip and will just add and subtract from it as I'm on the road.
5) I have done a lot of small trips around Europe and then the two big trips that were a month and 2 months long. A couple things to keep in mind.
Big cities are exhausting. If you spend a month doing Paris, Barcelona, Berlin, Vienna, Rome, Athens, Istanbul, Amsterdam, Copenhagen, Stockholm, London, etc it might be a bit too much. Just a bit. There's only so many museums you can go to before it's just not fun any longer. If you want to do the big cities then I would suggest doing fewer and taking your time. Also plan your trip out logically. I've done zig zags all over Europe and although it's exciting to start in Budapest and end up doing the running of the bulls a day and half later it's not very efficient.
You're better off spacing out the trip so that you have some castles, alps, museums, beach r/r, historical sites, cuisine, etc in even proportions. If you do too much of the same thing you will come home and not be able to tell the difference. It will all just blend together.
6) Obviously costs are the big thing. I'm noticing with my current planning that although costs have obviously increased they have not increased logically. Germany for example is very affordable all things considered. That makes no sense really. Generally speaking Eastern Europe is going to be much cheaper. Countries like Poland are not only affordable but often overlooked despite being an outstanding destination. If you have local friends in any country definitely take advantage of it. Norway, Sweden and Russia for example can be very expensive but not so bad and even cheap if you have a local there to help you out. Unfortunately for most people you'll just have to figure out on your own what you think your money is worth to you. In the 1990's before the Euro I felt that Greece was a good deal. Today I think it's highly overpriced and I would like to see prices drop by 50%-75% before I go back there again. There are simply too many other places that are a better value. Go there to see the Acropolis and leave for Turkey which in my opinion is a much better country to visit. If islands are your thing then there are others to go to. Hit up Santorini if you're on your honeymoon or something but besides that leave places like Greece off your itinerary if cost is an issue. You might have to leave a lot of places off your itinerary if you're really penny pinching. Focus on Eastern European countries like Romania, Bulgaria, and Poland. Bulgaria in particular is probably the best value I have ever gotten for my money. At the end of the day though if you're coming to Europe you need to see some of the big expensive cities so just suck it up.
Transportation already dealt with the next thing is housing. Hostels are not what the movies make them out to be. You will not be slaughtered. In fact most of them are really fun and I personally prefer them to hotels. If comfort is your thing just find a nice hostel and get a private room.
Websites like airbnb are awesome and can save you a money. You can rent a nice flat in a great part of town for less than the price of a hostel in some cases. As an example the 5 of us are going to stay in a nice flat in Pompeii as well as Rome and it costs less, includes parking, and is in a better part of town or right next to the main attractions. This might be harder to work out if you're travelling alone but if you're comparing to hotels it should come out ahead almost no matter what.
You can stay in a $200 a night place but that's your call. If it's a hotel all I really do is sleep there. At least with a hostel there are generally other travelers there to socialize with, a much better bar, and it costs less money. Europe is not Thailand of the 1970's. You're not going to be sleeping on a thin mattress on the floor with blood spattering on the wall with a moist room and a 30W lightbulb hanging from a chain and blowing in the wind. In Sweden hostels are nicer than many hotels I've stayed at. Plus with hostels there are some really cool ones. In Stockholm we have one that's on an old boat in the best part of town. I stayed in one by the airport that is a converted 747 plane. There's another one in Stockholm that is in an old prison. Another one is in an old medieval building. They're just really fun.
Use guidebooks, traveler recommendations, hostelworld and similar sites, and in a pinch use travel advisor. In Europe you should be wary of places with curfews. Don't stay at these idiotic places. I highly advise against any HI hostel in Europe. They're mostly terrible. I've been all over the world and the worst hostel I ever stayed in was the HI hostel in Zagreb, Croatia. Horrible. Arg!
7) Food is cheap. If anything don't drink like a fish in Scandinavia since beers here cost over $10 at just about any bar. Cocktails cost $25 and up. Save the drinking for Munich and Prague.
8) Attractions are cheap. There are also free days at museums, and if you're in a city like Rome buy the tourist pass which gives you two museums for free and discounts on the rest. It pays for itself.
9) Transportation in town is generally cheap. Buy weekend passes and books of tickets to save money.
10) Getting there. That's a big expense. I'm not an expert on this but I generally do ok. Right now for example you can fly with Norwegian Airlines to Oslo and Stockholm for about $300 one way. It was a bit cheaper before but prices are rising. Oakland, LA, and JFK if I remember correctly. I bought one of those tickets to go home for a visit. Mostly you need to look at where you are and what hubs you have available to you. I personally only know the connections for me to get from CA to Sweden so I really can't give you all the answers but use sites like Skyscanner and then once you have found a good fare go directly to the airlines website to see if you can get a better deal. Also consider getting to a hub in Europe and then flying with a budget airline to your destination. I can fly Stockholm to South America for a boat load of money but I can also buy a cheap Ryanair ticket to Madrid and get a much cheaper ticket from there to my final destination.
11) Lastly regarding fears and what happens if things go south? Don't worry. It always works itself out. Get travel insurance from worldnomads and don't be a stupid traveler. There are plenty of tips and tricks online for how to travel without being a target. Don't keep your wallet in your back pocket, don't leave the windows to the car open, don't dress in a Hawaiian shirt with khaki shorts, don't be loud and obnoxious, learn a few words of the local language, learn some of the local customs and try to read up on their history and culture before you get there, be patient and considerate and remember that you are not in the USA and that it's ok for things to be different.
Quite frankly the number one thing, and pretty much only thing, that Americans screw up with in Europe is thinking that everything here should be the same as it is back home. That won't fly. The reason you travel is to see things that are different. If not, then just stay home.
If you have any questions just let me know. I can PM you my travel map just to give you a sense of what I'm doing if you're curious.