You can certainly wing it.  Whether or not it’s stressful is an issue of personal style and preference.  If you’re hot and tired (like it’s 100 degrees, you’re carrying a pack, your feet hurt) and lost — will you look at having to go to hike to two or three places to find a bed (any maybe not the place you were hoping for) as a problem or not?
 
Having reservations for 1st and last (so you can work out how to comfortably get to the airport) nights is a good idea as a stress reliever, but other than that, it depends on whether you consider problems and “things not going the way you’d planned and/or hoped” as a good thing or a bad thing.
 
 
 
 

I winged it last year, and it worked out okay in France, but when I arrived to madrid I had to go through four hostels before i found a bed and i was tired after the ride from paris and the bag was heavy, and I really hated it.
so anyway what I begin doing because I guess that just like you I don’t like preplaning, every night before I left to another city I would book online a hostel for at least one night at my next city, this way nothing is written on stone, your trip is not pre planed but you don’t get stucked without an hostel when you arrive to a new city.
many hostels have free internet so it’s not a problem and it takes only a few minutes to book, which is much better than walking around the city for hours looking for a room.

Also depends on the season and the popularity of the city. Can be incredibly difficult or quite easy. Follow the other suggestions.

in a couple of weeks i will also be “winging it” in europe for 2 months…friends that have done that same thing have given me the same advice about booking a couple days before online especially if you have a long train ride or flight. at the same time, i think that half of the fun might be wandering around the town looking for a place[]

You can always wander around once you’ve dropped off your luggage.
 
If you do wing it, consider storing your luggage at the train station (if this option is available) before investigating. That way you’ll be less tempted to take an available but unattractive option.
 
Note that the best-value places tend to book up way in advance in tourist hotspots.

ya man its pretty stressful..it doesnt seem like it would be but trust me i found out the hard way lol just book like a week in advance and if something comes up u can always cancel

I can by no means say I winged it, nor would I want to.  I just came back from a group tour in Europe for two weeks with Contiki, and it was a relief to myself when i walked through the streets and saw the people who were winging it, knowing that i was showered and everything was already taken care of.  All power to you if you are winging it though.  Good Luck!

tictactoe:  are you an intern or employee of contiki?

I winged it for 6 weeks throughout all of europe with 2 girlfriends and it was fine. Yes, there was the odd stressfull moment but you know what? its all a learning experience. i learnt SO MUCH in those 6 weeks of travelling, booking online a week ahead in advance, bookings trains a few days in advance and just generally lookign after myself. I have no doubt that i would never have gotten that whole “done it myself” real travel experience.
 
Definitley do it yourself man…..its worth it.

Don’t wing it. A well planned itinerary gives you more comfort and peace of mind on your trip.
A spontaneous itinerary gives you headaches and regrets.
Contrary to popular belief, “winging it” is not that flexible. What if you arrive in a city and find all hostels booked? You’d have to pay 200 euros for a hotel. Or what if you arrive on a monday and find all museums closed?
If you do your homework now, you end up having fun on your trip.
If you don’t plan, you end up doing your homework while on your rip.

I only “winged it” twice on my last trip with a 50/50 success rate. The first time I apparently got lucky because tourists apparently decided not to go to Hallstatt that week so the fact that I was unable to book a room in advance didn’t mean I couldn’t find a bed.
 
The second time, however, I was trying to stay at a hostel in a town just outside of Frankfurt because there was soemthing I wanted to see there. However, after struggling to even find the right commuter line to get there, and not being able to get a map of the place, I had to wander around in the rain following rudimentary directions on how to get to the hostel. Then when I arrived, the pricks at the desk informed me with a chuckle that they were entirely full. Thanks for not answering the phone motherfuckers!!!!!!!!! [:@] They seemed to think this was the funniest thing in the world, too. So I had to find my way back to the S-bahn station, in the rain, and it was dark by then…. and then had to walk around Frankfurt am Main looking for a hostel. I was lucky enough to get a bed on my second try (thanks, “Letsgo!”).
 
But obviously after this, I didn’t feel like doing a goddamned thing, and just used the rest of the night to make phone calls to the States. So, would I recommend “winging it” on purpose? No way []

i winged it on my last trip, had no problems doing so at all. i guess because after austria, there were no places that i just HAD to see, as i was happy just being anywhere in europe, so my philosophy was that, having a rail pass, if i ended up in a place that was completely booked, i would just hop on the train and go somewhere else. although that never happened. i prefer the freedom of winging it, it allowed me to leave rome the very same day i got in when i discovered it wasn’t to my taste, and to spend a week in zurich when i met someone at the train station (when i was waiting for my train to vienna) who offered to let me stay at their house, even though i had no prior plans on staying in zurich at all. no stressful moments at all. your trip should be an adventure, if you have to put your stuff in a locker and wander around all night, so what? it’s an experience.

I winged it for 7 weeks and it was just fine. There is no reason to hike to hostels for a room. Use a pay phone when you get to the train station or even better before you get on a over night train. My travel guide had phone numbers to many hotels and so did the train stations. The train station will even call and make reservations for you. I found a place to stay in every city I stopped in.