2 Americans 1 male 1 female in their 30's traveling by plane from Amsterdam to Italy, then a train back through to Switzerland Austria, Germany, Czech Republic, back into Germany again then Amsterdam. any and all tips appreciated
Answer on Will i have a difficult time at any of these points?
No, you shouldn't have any problems. Just remember to bring your passports. Your tourist visas should be fine as long as you are both American citizens.
At the airport in Amsterdam you should look for the passport queue for non-EU nationals. The queues are long, but you can see the EU flag over the queues for EU citizens only.