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Lisbon is an overnight train ride from Madrid. Lets you out in Lisbon about 7:30 a.m.

Be sure to spend at least two whole days in Sintra. 45 minutes west of Lisbon by train.

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My subjective remarks would be:
Tuscany is quite beautiful and food/ wine fantastic. But the cities are very touristic and expensive. If you want to get more in touch with locals, I would rather stay in one or two little towns in the countryside and rent a car for visting the cities. As a cheaper and somehow more original alternative to Tuscany you could also go to Southern Italy or even to Sicily.

One or two days for Venice should be enough. Rome - maximum 3 days as you´re not that much into culture. Milan - no need.

You should include Lisboa. Affordable, easy going, good nightlife. The Algarve coast in Portugal is beautiful but quite far away from Lisboa.

Berlin, Paris, Barcelona - definitely. Madrid can be a bit exhausting. Instead I would go to Andalucia (Sevilla, Granada...) and enjoy Tapas.

Brussels - not really, if you ask me.

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The train from Madrid to Lisbon takes about 8 hours, and shall cost around 50 euros return. But you can take an overnight train with a sleeper, so it will save you a night accomodation. For Lisbon i would say two days is enough. The most sights are within walking distance, except Belem (where you go for the best custard tarts in the world). If you rush, you can see all the sights in 1 day, but 2 days will be more relaxing. And try to catch a fado night in one of the bars in the Alfama-district. Best way to see all the sights in 1 time, is to catch a ride on tram 28. And, as gawkabout said, go a day to Sintra. take a bus, or hike to the top of the village, and youll be rewarded with one of the best views ever, overlooking the wonderful weird Palacio de Pena. But although Lisbon is wonderful, ill prefer Porto myself. Its a couple of hours from Lisbon, and is beautiful. Stop on the way for a day in Coimbra, the Cambridge of Portugal. Porto is on the beach, so thats good. It has a beautiful historic centre, and a beautiful bridge over the Douro River, build by Eiffel. Stay in the Oporto Poets Hostel. Also, the surroundings of Porto are beautiful too. There a dozen cities like Braga, Guimaraes and Aveiro, which are beautiful too. Going there myself again this december too. In Porto 2 days is enough to see the main sights, but when i was there i stayed two weeks, cause i didnt wanna leave....From Porto you can consider to take a bus to Spain's Santiago de Compostella, if you have some time left.

In response to other questions. I dont think Icelandair has an open-jaw-ticket, so it might not be the easiest way. But you can always get a cheap Easyjet plain from Athens to Amsterdam, and then take the connecting plane. Youre not the first one to see 'In Bruges' though. It really is a beautiful city, as is seen in the movie. But after this the movie, the tourism in Bruges exploded. So expect big crowds. But its still unmissable. Gent (or Ghent) will be a less touristic alternative, but they can easily be visited both by train. In response of 'Poeppes', Brussels is quite dissapointing yeah..Although the main square is beautiful.

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If you don't buy a round trip, you don't have to go back that way. Go see more of Portugal. Then turn right.:)

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Argh!!! I posted a long response to the thread and went I clicked on "Post Message" it didn't pop out!!! Should have copy/pasted it beforehand. I learned my lesson this time. Typed everything on Word and copy/pasted it... Anyways, here's take two.

AWESOME ADVICES AS ALWAYS, salamat gid. (Thank you in Tagalog.)

I've listened and considered a lot of amazing options and suggestions from everyone and this is the breakdown. 
So here's the scoop guys: My almost-final itinerary. 

Fly from Seattle-Frankfurt   
Train from Frankfurt-Berlin (5nights/6days)
Fly from Berlin-Amsterdam (3nights/4days) 
-Haarlem
Train from Amsterdam-Antwerp (4nights/5days) Visiting and staying with a friend. 
-Bruges
-Ghent
Train from Antwerp-Luxembourg(2nights/3days) Visiting and staying with a friend. 
Train from Luxembourg-Paris(4nights/5days)
-Loire Valley -(2nights/3days) Should I come visit this place to unwind? I heard they have some nice castles and villages around. 
Fly from Paris-Italy (Not sure in what order I should do the other cities. Any recommendations?) 
-Rome (3nights/4days)
-Naples (2nights/3days) Also going to Procida Island as suggested by egallerie. It may be the closest thing to Greece!)
-Florence (3nights/4days)
-Modena (2nights/3days) Visiting and staying with a friend. 
-Venice (2nights/3days)
fly to Barcelona (4nights/5days) Visiting and staying with a friend. 
-Andalucia (Seville and Granada, 2nights/3days)
Train from Barcelona-Portugal (overnight)
-Lisboa (3nights/4days)
-Porto 
Train from Portugal-Barcelona (overnight)
Barcelona back home to Seattle 

As you can see, I have removed some big cities such as Brussels, Milan, Madrid and Greece and replaced them instead with the small towns/cities nearby. For Amsterdam, I would love to make a side trip in Haarlem for the day which is just minutes away. Fun fact that I read somewhere: it has the exact distance from Amsterdam as Haarlem in NY from the tip of Manhattan. I'll maybe spend a day there looking at one museum, bike around this cozy town. Bruges and Ghent is a go especially after reading this thread! The latter was also once ranked 3rd in the most authentic destination by Natgeo a few years ago. Tapas, nom nom nom. The beach would be perfect to end my trip, thank you for suggesting this. I saw some breathtaking pictures online, whew.

Haven't bought my ticket yet, wanted to talk more before purchasing the real deal but I am planning to do so this week. Icelandair.com has good deals but yes, they don't have the multi-city option. I figured it's better to have more than less. I have decided to increase my budget to $6,000.00 including my airfare. I have been checking online and I found one from Seattle-Frankfurt, Barcelona-Seattle for $835.00. Total nights counted were 44 including my overnight train to and from Portugal. I gave a leeway of another 4 days (which can be too much) but just in case I fall in love with the city and decide to stay a bit longer, so a total of 48days, budget of 80euros/day (to be realistic. some days I may spend less, some I may spend more), 500euros for travel expenses (bus/train/flights). I've checked the prices online, I may buy my flights ahead but the train can wait… This will give me 4,300euros for everyday expenses excluding my ticket to and from Seattle. I hope this is doable.

Any more advices and suggestions are welcome. Thank you so much to everyone! You've been a great help in planning this trip :) I can't wait for it to materialize!

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Yes! It published! Kampay! (Cheers in Tagalog. Fun fact: it is the same in Japanese)

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How do you count the travel times. 2 nights in a city does not count for 3 days, its one day and some hours on day 1 and day 3 + time vasted to get orientated in a new place.
I would spend more time in Andalucia and skip Portugal, too much time to travel back and forth.
At least 3 nights in Seville, 2 in Granada and something in between in a smaller town like Ronda.

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Getting lost is a bonus. Take advantage of it.

Learn something!

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Kampay! (Cheers in Tagalog. Fun fact: it is the same in Japanese)
Real fact: the Japanese word 乾杯 kanpai (litt: dry glass) does indeed mean "cheers", but not in the sense of "thank you". It's what people say before they take a drink.

Regarding your itinerary, it's better than the original one, but I'd like to add just a few comments:
1. As akana already pointed out, you're counting days and nights the wrong way: 2 nights = 1 full day, not the other way around.

2. Your itinerary derails in Spain: 2 nights (= 1 full day) to see both Sevilla and Granada is impossible; one-way journey time is 3 hours to 3 hours 40 minutes, not taking into account that in both cities the train stations are located quite a distance from the main tourist attractions.

Train from Barcelona-Portugal (overnight)
I think you mean Sevilla-Lisbon? In that case, note that there are no direct trains, you have to travel to Madrid first and change to the night train there. Travel time is at least 13 hours, and in Madrid trains arrive and depart from different stations

Train from Portugal-Barcelona (overnight)
Just to be sure: when leaving from Porto (Campanha station, which isn't centrally located) this is a 17.5+ hour trip involving a change of trains in Porrino and train stations (by metro) in Madrid.

Much as I like Portugal, I'm inclined to recommend you skip it.

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Oops, my bad. Disregard the days but the nights are the ones to be considered. Ahhhh, then maybe instead of Portugal, have Madrid. Akana, yeah might have to extend my stay there. Thanks for pointing that out Aribo, hmmm. Looks like Portugal might have to be for another time then... We'll see, but thanks again people! This is much appreciated! Will purchase tickets soon, yahoo!

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Yeah. I'd suggest Portugal as a worthy trip of its own. It'll be cheaper too.

Next time.

Spain is as big as Texas, without the panhandle. Different cultures in different regions too.

Take it slow and enjoy.

I meet fellow yanks who say they come back to Spain every year."The more we learn, the more we want to know."

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hi there just reading your post ive been living in london for the past 2 years and travel round europe all the time i agree that in munich town itself there isnt much to do however i went to oktoberfest last year and spent 5 nights there it was a perfect amount of time i would have not stayed so long unless it was for oktoberfest.also im currently in portugal right now i wasnt sure on going there but its the most amazing place we caught a bus the company is alsa from madrid to lisbon itll cost you about 30 euro and the bus ride is about 8 hours so we booked an overnight bus also alsa buses have free wifi ,if you go to porto which is so pretty in portugal id stay like 3 nights also check out the gallery hostel there we stayed there and its the best hostel we have eva stayed in,lisbon id stay 3 nights and u have to go to lagos if u go to portugal the beaches are amazing id stay 4 nights hope this helps a little .we also found that to avoid huge lines anywhere purchase any tickets online and print ur tickets of there's a seperate line and u wait like a few minutes its soo good.hope that helped also ask me any other questions u have if u like

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Portugal would be a worthy, beeezar trip of its own. Cheaper anyway.

I think Spain history here and there, would be good healthy food friendly if you are, sojourne. youtube "Muslim History of Europe" chapter 1-4 would be time well spent on a hot day. Tose chapters cover Spanish city states. Amazing Well done.

Fellow yank families tell me, "We come back to Spain every year. The more we learn, the more we want to know."

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oh wow i didn't even realize i dunno what went wrong there sorry bout that.anyways i was also gunna say after looking at the cities you want to visit.

i think 5 days in Berlin is far to long 3 days and ull see everything.
4 days in Rome.
i found Milan quiet boring it really doesn't have much to offer except for really expensive food and shopping.
also i would stay maybe 3-4 days in Madrid its quiet small i saw everything in one day.
equity point in barcelona is a good hostel to stay,its really central.
porto-gallery hostel is amazing
lisbon-lisb'on hostel(it has an amazing roof top terrace overlooking the river)
lagos-carlos house(so central and the owners are so nice)
i cant remember half the names of the places ive stayed sorry.

look on hostel-bookers and homeaway.co i book all my accom on these sites,theres pretty good places even for 10 euro upwards.

also with your budget it is posable right now i dnt spend anymore then 10-20 euro a night on accom, and i pick places with kitchens so i can cook dinner not buy out, you save alot of money that way.somedays youll spend more like on a travel day when you have to pay for a train/bus whateva ticket,somedays ull spend hardly anything.
i had an old student card in australia which i lost but whenever i line up for something i say im a student and they ask to see my card i say i lost it or i forgot it today,hasnt failed me yet.

and look on skyskanner for flights you can type in your destination and itll come up with all different possibilities on where you can go and it also compares all the airlines.

Dubrovnik(one of my favs),Palermo,Taormina,San Benedetto del Tronto,florence,sorrento,Monaco,Nice,Prague are some really nice places to see.
ive also found that alot of the time the bus(coach) is like half the price of a train ticket and sometimes only a few hours difference between them.

Edited by: kiraleejoy

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Talk with us b4 buying any plane tickets. Don't book all beds b4 leaving home.
Open jaw is most practical.

Now where did I put my pith helmit?!