I have enough $ saved up for a long, nice vacation. 3 weeks - 1 month type of thing. Haven't been to Europe [ France to be more precise ] since I was 8. I'd like to explore the old continent.They're is so much to see tough than I'm not sure what to prioritise, so some hints would be appreciated.
I'm undecided in beetween going for familliar destinations (French speaking Europe) or the intriguing (Germany/Sweden/Scandinavia in general). Maybe I'll mix the 2.
What I'd like to do :
-See historically significant sites : bonus points if it dates from the Roman Empire era, I love that shit!
-Eat good local specialties. Bonus points if it's hard to find in North America
-Chat with friendly locals : I speak French (native language) and English fluently. I can understand some Spanish. My knowledge of German is, sadly, very limited. I wouldn't like to be in a place where I can't communicate with the local population.
-Not break the bank
I'm open to any suggestion in Western and Northern Europe

Also what is the best way to travel once inside Europe? Is renting a car worth it?
Also, accomadations. I'm not looking for luxury, so long as I have my own bed and my own shower, I'm a happy man. Just need a place to crash once the day is over. Should I book in advance for a summer trip?
Also, do canadian bank cards work in Europe? I'll obviously get some euros before leaving but what if I run out.
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You'll definitely want to book places sooner rather than later. Look into hostels to make it easier on your budget.
I believe that there are some train passes that work between European countries, so it might be possible to get one of those and travel between the countries by train. Might be cheaper than flying and, if you don't mind the added travel time, you can sometimes find night trains and as such get lodging over the night through that. If you travel during the day you can get to see the nature somewhat as well.
Given that you speak French, I think a visit to Paris might be in order. It is a town with lots and lots to see, so unless you plan to stay there for quite a few days, look up beforehand what you wish to see. Oh, and if you want to go to an amusement fair I can recommend Park Asterix, which is themed after the comic character by the same name. Visited there several years ago when I was young with my family and had a good time.
Another point regarding language: I think that the Scandinavian countries (or at least Sweden, where I am from) tend to be excellent at speaking english and you would be hard pressed to find an middle aged adult here who does not speak it at least passingly.
If architecture is what you want to see, Sweden might not be the best choice, although we do have some rather pretty nature at least. I am especially fond of the west coast around Västra Götaland and Bohuslän (both Swedish districts), but I might be biased since I live around there.
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Major historical roman sites are mostly in the south of France (Lyon, Reims, Nimes), though it's hard to beat Rome and the immediate surroundings of course. And you could consider Instanbul too, though conversation with the locals will be a bit harder, though Turkey has become a major tourist attraction in the last two decades. I don't think much is left of the Roman frontier along the Rhine in comparison, though there is some stuff around Trier (which briefly was a Roman capital during the 3rd/4th century)
Things to consider:
July 14th is the biggest holiday in France, and pretty close to Independence Day in the US. (Fireworks, barbecues, military parades). It might be fun to be in France at the time.
If you are in to cycling at all, you could plan to see a stage of the Tour de France which runs in roughly the same time frame (2nd week of July to end of July usually).
Throughout Europe it is Festival Season in the summer. If you want to immersive yourself into music and youth, it should be pretty easy to plan a 3 day trip to one of these. They come in at €150-200 and you have to bring a tent usually. Your shower rule would definitely be broken though, and having a day or two with little to nothing planned afterwards might be advicable.
A good fitting city might be Barcelona. It's in the Northeast of Spain (a little more bearable temperature wise in the summer and not so far away from France), it has great beaches, great art (Dali) , great architecture (Sagrada Familia) and great food (Spanish cuisine is excellent in general, and from what I gather relatively unknown in the US), and it's a young festive city.
On the other end of your map is Berlin. Kind of far away from everything I mentioned (by European standards), it is of course a pivotal city in the 20th Century, it's absolutely booming with everything that comes with it.
Think about how you will travel:
Visiting major cities should probably be done via public transport. The quality is pretty good in urban centers, and everywhere north of Paris has excellent train connections for intercity travel, and car rentals get more expensive if you make too many miles in a short timespan. But if you are visiting smaller places, you probably want to rent a car. If you are planning to go more than say 300 miles, then you can get a plane ticket for really cheap by booking early with one of the budget liners. Under 300 miles trains are probably faster though not cheaper, mostly because you can just show up 10 minutes ahead of time in an urban railstation and step on one, instead of dealing with the lines and lines of airports that are outside the city.
See if you can get a bank card / creditcard with a Maestro logo. Those basically mean that it'll work on any ATM and almost any store in Europe. Creditcard acceptance is not totally universal, though restaurants are pretty good at it.
The place to be for Roman excavations and the likes is Pompeii, all the way in southern Italy, there is also lots of it in Rome (the Colosseum, to name one!). There's all kinds of tourist books and websites to plan your trip around this subject.
There is also lots of Roman stuff in Paris, most of it is in museums (the French conquerors liked to bring stuff back home with them), but there's also a Roman arena that is free to visit and some other stuff from back when the place was called Lutetia.
Local food: France and Italy are fantastic. There's decent food everywhere, but unless you're a huge foodie it's not worth travelling for food.
Cheap: hostels, airbnb.com, small bed & breakfast places. Book in advance because it's always more expensive and a huge headache to go hunting for a cheap place to sleep while you're busy with getting to places.
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Use trains and other public transport. Renting cars is expensive and should only be done if you're planning to visit small towns and such.
Summer is high season. Everything is more expensive in the summer. Traveling during spring or fall is much cheaper, and it's still shorts weather in May/September, especially in the south.
Spend at least 3 nights in a city. Anything less, and you end up spending more time traveling than you do sight seeing. Take day trips to nearby cities, if you get bored; day trips waste far less time than changing hotels. For example, during my 8 night Amsterdam trip last fall, I day tripped to Haarlem, Zaanse Schans, Utrecht, and Den Hague, leaving 3 full days (and 2 half days) in Amsterdam itself.
If you are in Germany, rent a nice car (like a BMW or Audi) and drive the Nürburgring. No speed limit and lots of curves makes a perfect drive. No need to rent a car anywhere else in Europe, in fact, I'd say fly or take the train, but make an exception for Nürburgring.
It's worth pointing out that normal rental car companies forbid the use of their cars on the Nürburgring, which means that, at the very least, insurance won't cover anything that happens on there. No idea what other consequences there are for breaking the rental contract, although I'm pretty sure the company will not rent to you ever again if they find out. There are places near the Nurburgring where you can rent cars specifically for use on there, but that's obviously a lot more expensive. AFAIK you still have to pay for damages you cause to the track or guard rail yourself.
For train travel, I just noticed that eurail hasn't been linked yet. Could easily be the cheapest option for train travel.
Provence, if you are not familiar with it, is a region in south eastern France and should fit your needs quite well, as it has a huge array of Roman ruins, nature (beaches, mountains, rivers, etc - for hiking or otherwise) and fantastic food and drink. Plus they speak French. I spent a week there last summer and it was one of the best holidays I've had in a while. Kayaking down the Gard river, under the Pont du Gard is something I think I'll never forget
http://en.wikipedia.org/wiki/Provence#History
http://www.francetravelguide.com/top-10-things-to-do-in-provence.html
http://www.roughguides.com/destinations/europe/france/provence/
You can get there pretty easily from Paris (several hours by high speed train), then you are well placed to move on as Marseille is a major airport hub for Europe.
Taormina sits on the coast, close to Mt Etna and site of various settlements reaching off far into antiquity - the shot below from the Greek theatre on the crown of the bluff over the town to Mt Etna is just one of the best things you will ever see in Europe
http://slowfoodsicily.com/index.html
http://www.italia.it/en/discover-italy/sicily.html
Fly into Paris. Spend at least a little time there, it is one of the greatest cities in the world. Take the train to Provence and soak up the Roman ruins, beautiful landscape, and delicious food for 5-7 days. Visit markets as often as possible. From there head to Barcelona, but stop in Carcassonne along the way. The fortified city as a whole remains one of the more memorable sites I've visited in Europe, and there are elements dating back to the Roman empire.
Head to Barcelona from there. Beautiful city, amazing architecture, and fantastic food. Splurge for a night and stay at Parador Cardona nearby either before or after your time there. It's a castle turned into a hotel, and I booked it for a friend on his honeymoon years ago and he and his wife loved it. They have smaller rooms at just over 100 Euros a night including breakfast, and from what they told me it would be well worth it.
Venture further into Spain from there, or spend more time in France before heading south. My most visited sites in France are all in the Normandy area, but that's mainly because I used to plan and escort military history tours for American veterans groups. It's a good area for a mix of modern and older historical sites though, between the battlefields, cemeteries and monuments and things like the Bayeux tapestry, Mont St-Michel, and all sorts of history in a city like Rouen. If you have any interest in heading to Normandy let me know and I'll see if I can dig up an old itinerary or two that you could look through for ideas.
I'd almost thing he would be best to head to Andalucia instead of Catalonia if he ends up spending a lot of time in southern France, if just to see something a bit different. If he hangs about in that area he could also pop across to Morocco for day trips as well
Last time I was in Europe my itenerary was as follows:
Barcelona -> (bus) Zaragoza -> (bus) San Sebastian (one of the most beautiful places I've seen) -> (bus) Bilbao, mostly to see the Guggenheim, and then flew out of there to Barcelona to Munich for a week to meet up with people
and then back to Spain where I did Sevilla, Granada, and Malaga
If you want to do france + Spain, you could take that first part of my trip (Barcelona - Bilbao) and add in either northeast France after, or Southern France before
that would be fun!
San Sebastian really is amazing though, food and city and beach
Zaragoza and the surrounding area seem pretty packed with Roman remnants too. The old Roman forum complex in the middle of the city was well worth a few hours
Thinking about it, understanding maps / restaurants menus / road indications should be pretty easy for me in Portugal, Spain and Italy since their language share the same latin roots than my native French
I'd really like to go to Germany tough. Is it possible to enjoy Germany without speaking their language? I only know the very, very basics of the german language.
Again, I know its not one of the places you mentioned, but I found it to be really unique and different from paris, rome, london, etc. Just worth a thought!
I think you should also look into visiting Eastern Europe. Prague is beautiful, as is Budapest. Also consider hanging out a few days in Vienna because it's lovely.
Anything in Northern Europe is very very expensive, so if you're worrying about breaking the bank you should throw that out of the window altogether.