first Europe trip

Europe is a fascinating place and you will never forget the experiences you have there.
It is also geographically bigger than some people think.
There are resources here and other places online that will help you get a realistic idea of travel times.
You mentioned getting to "meet and know" the locals--that is sometimes a challenge.
This site will help in what can be a confusing situation of travel planning, and you should also explore other resources, books and websites.

Have you read any guide books on Italy or Amsterdam yet? Check out RS' "Europe Through The Back Door."

I see that you are not interested in structured tours. Perhaps though, you can use them to gain a few ideas to tailor make your own. You have some time to play around with different things.

pwood4 You really would get a lot of help in reading the Europe through the Back Door guide first. If you want the real backpacking experience, just plan on starting in Amsterdam, and ending in Italy, and figure out the middle when you get there. I wouldn't worry so much about keeping him entertained. If you need more structure, do take a look at the RS tour itineraries, and you'll get an idea of some reasonable itineraries.

What about doing half tour/half on your own? I suggest this because you seem overwhelmed with the amount of time you have. You could do a 10 day tour somewhere to start of your trip and then continue on your own. Not all tours are large group/rushed/focused on just the large cities. There are the Rick's "My Way" tours or tours based on cooking classes or hiking every day.

Start with a map :-)
break down the trip to chunks

you could go into Amsterdam and fly home from Rome.
Plan start and end lodging.
Set up some airfare searches on kayak.com

better yet have your son do the research :-)

enjoy the planning and the trip!

pwood,

As others have suggested, I'd highly recommend reading Europe Through The Back Door before you get too far in your planning. It provides a lot of good information on "how" to travel well in Europe, and great tips such as Itinerary planning. It would help to know where you're travelling from?

You've already got a start on choosing destinations - start in Amsterdam and finish in Rome. Now you'll have to figure out what to put in the middle. I'd suggest that both of you make a list of places you'd like to see, arranged in order of most favourite to least favourite. That will give you a starting point to start choosing places to visit. Don't worry about the details yet, such as hotels, transportation, Railpasses or sightseeing. You can work that out once you've finalized a list of places, and the group here will be able to provide lots of guidance on those.

One point to mention regarding Amsterdam, is that the authorities may be tightening up the regulations at the "Coffee Shops" and preventing foreigners from making purchases there. I haven't been following the situation to closely lately, but I'm sure one of the others here will be able to provide further information.

Could you provide some idea of the places you're interested in seeing? I'm surprised that London wasn't mentioned.

Using open-jaw flights would be the most efficient method, so that you don't have to waste the time or money to return to your starting point (which is partly why I asked where you're travelling from - others here may be familiar with the best flight options from your airport).

Hostels are a good way to save money, but I find that a mix of Hostels and budget hotels works well, as it's nice to have some privacy some of the time, rather than "communal living" for an entire trip. In some cases, the cost is not much different.

Even at that time of the year, I'd suggest pre-booking some accommodations as it can still be busy in some parts of Europe. I much prefer to have some idea where I'll be sleeping when I arrive in a new and unfamiliar city, and that also provides the ability to choose which part of each city I'm staying and the price range.

Good luck with your planning!

I would start in Amsterdam and explore the Netherlands first and then head to Ghent Belgium and then thru Germany and Austria and end in Italy.

Trains. Maybe pre-purchase some longer routes. I doubt a train pass would be cost effective.

Thank you for all the great suggestions. I am fortunate that a close friend works for United and is getting us buddy passes. We have the freedom of flying in and out when we want or Can! I have ordered the book everyone mentioned it should be here any day. Thank you so much for reminding me to let my son plan, and not worry about everything at once. They brain just takes off. Everyone helped ground me again. That idea about taking a short tour then head out on our won sounded really good. I'm a all or nothing kinda girl so it helps to see there is a in-between s. I look forward to sharing with all of you and picking your brain.
London wasn't on the list because I have been there a few times its been very long ago but I was in a relationship with a man from Ireland way back we traveled to Ireland to visit his mum and Da and London, Then Greece. I didn't consider that Europe, I guess lol. Tristan (my son) has been to Madrid on a school trip and Scotland with a friend. He might want to go to London. Trying to get him to sit down and plan is a challenge. Now that he just finished school it will get more real for him. Rambling sorry

@pwood :)

The other part of the fun in traveling is the planning - it is exciting. I hope you and your son have a wonderful trip!

Lots of good advice above and the book will certainly help. To paraphrase, choose your destinations first, in a logical path, and worry later about booking hotels or calculating the cost of train travel. When you have your wish list laid out, it makes sense to cut off the "oddball" that's furthest from the others, perhaps Spain or Greece, or to fly those longer legs, even from a neighbor country. A single country can show you a lot of variety in different regions and between large and small towns, so you don't have to venture too far to keep the experience fresh.

As a budget parameter, you would expect to pay about $825 per person for a Eurail Global pass covering your 10 longest days of 1st-class travel on the continent (not including Britain), plus some seat or sleeper reservation fees, or $1100 per person for the next-larger options.

You said you decided quality is better than quantity. I agree with you on that. If you and your son will be away from your home for four weeks (28 days), I recommend : go to Amsterdam and Germany and Italy. It might be best to fly from Germany to Italy. If a traveler goes to many destinations that are far apart, the traveler uses much time for travelling between places. I do not recommend doing that. I like the replies from Ken and Laura. I recommend : try to get your airline flight reservations (for departing in September) this week, if you do not have that. Is the railroad train pass that you mentioned a good value for you ? I do not know. I suggest : when you decide what are all of your destinations in Europe, calculate the total expense for point to point train tickets, and see if that is higher than the price for a railroad train pass. And remember, low priced train passes are available for travelling in trains in a region in GERMANY. You did not say what country you are at. What country will you travel from ? If it is the U.S.A., which state ? For help in deciding where you want to go in Germany, I highly recommend reading the travel guide book "Rick Steves GERMANY". That book is at public Libraries in the United States of America. Reading this year's edition of that book is not necessary for learning about various places in Germany. And I think the travel guide book "Rick Steves' ITALY" is very good and helpful for planning travel in Italy.

Forget about the getting to know locals ,its such a tourist fantasy, you may "get to know " you waiter, or your bakery clerk etc but when you are moving around ecry 4-5 days you are not making buddies, you are perhaps chatting a bit with people who have to talk to you as you are a customer. People who rent apartments and stay put for months can attest that most locals are not that open to true friendships with tourists.

So why am I telling you this?

Because a way of making some friendships with foriengers is by avoiding hotels and staying in hostels. There your son will have a real opportunity to meet youths from many Europe on countries who will be far more willing to chat and share a drink etc. My 18 yr old nephew did Europe by himself a few years ago , part on a tour then two weeks on his own. He still converses with kids he met from UK and states?

Going to small towns does not make it easier to befreind
locals in many places they are more closed off then city folks .I was born in Europe and spent many summers with relatives months at a time, and the friends I made were through family connections .( if you have family
or friends you can look up I strongly encourage that, that is a great way to mingle with locals)