There are a few places I would strongly recommend for the timid and first time traveler. The top 2 candidates for “destinations with training wheels” are Paris and Amsterdam. The best part about these cities is that they will become old friends for those few days of starting off and finishing up future visits to Europe and points beyond.
What makes Paris such a great city for anyone’s first time? Well, she’ll be gentle. The reputation for French snobbery and haughtiness is greatly exaggerated. They are proud, yes, and just a bit aloof but that is not the same as being contemptuous of strangers.
Think of a cat. If you go chasing after a cat it will stay out of reach and ignore you completely. You are not speaking it’s language. You are on the cat’s turf, give it the opportunity to examine you from a distance and it will make the first approach. Even a cat understands respect. 
Here is where the training begins. Rule one, learn a few words of french: it isn’t hard to do and talking english louder and using lots of hand gestures won’t do jaques merde. If you wish to penetrate that gallic aloofness just say, “excusez-mois”. Even if that and ‘bon jour’ are the limit of your parlez-vous, it will be sufficient.
Because you are trying.
The fact is most Parisians living in the main tourist zones of the city speak and understand English quite well. There are some who don’t but they will know enough English to tell you that much and go find someone who can help.
The 2nd reason it is such a wonderful first city is the food. Not just the famous restaurants and the wonderful sidewalk cafes but the pastry shops and butchers, the green grocers and the specialty shops.
Might I suggest starting out with a boulangerie. Look at the sign, look at what’s in the window, walk in the door and look around. Examine the display cases and take your time.
The clerks won’t bother you other than to say ‘bon jour’ to which you reply, drum roll please, ‘bon jour’. Very good. See how easy that was? Once you’ve finally decided on something to try, smile at the clerk and say…come on, you know this…”excusez-moi” and point at the item.
Here you may feel bold enough to attempt to say something else to which the clerk may smile or may stare at you with total indifference.
Smile. Really. Not that much, you look slightly demented. Just a natural, easy, genuine smile. Then, if you were asleep when Madame Binet was teaching basic numbers in Grade 3, start using sign language to indicate how many of those gargantuan Palmiers or chocolate croissants you’d like (to cram in your face as soon as safely 
parked on a bench).
Don’t know what it is? It’s a bakery, how bad could it be? Sweet, crunchy, maybe a bit of something custard inside…What’s not to like?
If you don’t feel like going off on that much of an adventure stick to the cafes. In the afternoon it is expected to sit at an outside table, face the sidewalk and watch the people walking by. ‘Cafe creme, sil-vous-plait’. Feeling a bit peckish? then ask for a ‘sandwich jambon et fromage’. This is exactly what it says: ham and cheese on a baguette, no butter, no mustard or lettuce or other frou-frou. It will seem a bit dissapointing at first but in a day you will ask for it again and love it.
Whatever you do, do not order a Croque Monsieur thinking it is the same thing. You will spend the rest of the 
day feeling like the monkey who swallowed a billiard ball. It is great for lunch or even for breakfast but never, ever attempt it as a mid-afternoon amuse bouche.
If in doubt about what to have at any time of the day or night, one word: crepes. With ham, cheese or with cinnamon, lemon juice and sugar or, pardon me while I drool, bananas and nutella….oh baby….
Next lesson will be the Metro. Possibly one of the greatest gifts to a tourist ever created. It takes 2 minutes to learn. If you get lost and start to panic, immediately go outside. Find the nearest cafe, grab a cafe creme, a crepe and sit. Watch the people walking by. Before you know it the panic is forgotten as you hear yourself say, “Mon Dieu, I’m in PARIS!”
Now, smile.
