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Complete International traveling noobie - Please Help!

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My husband and I have decided that we want to take the leap and plan a trip to Europe. As is my customary style, I began pouring over traveling books, message forums, and hotel websites. I immediately purchased Fodor's London 2012 for my Kindle and begin spending my mornings bleary eyed from the lack of sleep the night before.

This started a week ago. Since that time we've gone from London > Paris > Amsterdam to Rome > Venice > Athens back to London>Amsterdam (where we have stopped for the moment). We have flip flopped back and forth over what time of year to go, what type of place to stay (hotel, hostel, B&B), the list goes on and on. I spend most of my lunch and breaks reading the glorious posts on this website, searching for one that will say exactly what I need it to say.

Tonight I have finally summoned the courage to post my own!

Help me.

There's just so much...what to do?, where to stay?, is that a good price for that?, how do I budget my time? What’s more important, Stonehenge or Westminster Abbey?...ArggHH!

So here’s the deal. I have posted all the info I have, so far, below. I also laid out just some basic questions have been tough for me to narrow down. Most of the information I’m looking for is on London for the moment. (Anyone who has done a trip similar to this, please feel free to post about any of the cities below).

My#1 question is - Can this be done on my budget without watching every single red cent that I spend (but still being cautious and responsible)? We don't expect 5-star service/food, but we want to have a good time without worrying.

Our budget:
$5,000 (a little wiggle room, but not a lot)

Travel time:
10-14 days

Time of year:
We're low-key people who would like to avoid the crowds. We are currently leaning towards May or late October/Early November.

Airfare/travel:
Where is the best place to buy? Best time to buy? What to look out for? (I've only flown once and that was to Tampa, FL from Louisville, KY) What is it like on an international flight? Are they the same size as the planes that fly domestically? I can’t imagine sitting in a seat like that for 7 ½ hours.

Places we want to visit:
London>Amsterdam (if only 10 days)
London>Paris?Amsterdam (if allowed 14 days)

Best modes of transportation:
I’ve heard of this Oyster Card in London, any details? Where to buy, price?

And possibly my biggest question:

Where to stay on a budget?
I would like a half-way decent room (some likes would be - Wi-Fi, Queen/King bed, en-suite bathroom, close to the tube, good neighborhood) for right at or below $100 a night.
I have read about the overnight ferry from London > Amsterdam and we do plan on using that for two nights (there and back because flying open jaw to London and back from Amsterdam seems to be more expensive than round-trip to London).

And lastly, please feel free to share any little, golden pieces of traveler knowledge that you like. Pictures are also always welcome!

Many thanks!
Jbailey

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