Itinerary Pointers and Reservations

My friend and I are traveling through southern Germany and Italy for 3 weeks and leaving at the end of next month. We could really use some help! We are both 25 and planning on buying the German Rail Pass with the extension pass for Italy. This is what we have so far...

Day 1 Arrive in Munich (Tues. July 29)
Day 2 Munich
Day 3 Munich
Day 4 Munich--> Garmisch
Day 5 Garmisch /Mittenwald
Day 6 Garmisch--> Salzburg
Day 7 Salzburg
Day 8 Salzburg-- Verona via Munich

Is it imperative that we book any of the trains besides the night train to Verona in advance? Does the GRL seem like a good deal with this itinerary? What about hostels? Your input is appreciated!

There's no night train to Verona(unless you really mean to arrive at 02:37 in the middle of the night), only daytime trains.

The German Rail Pass is a waste of money for these short hops.

The best deals for you:

In Bavaria:

http://www.bahn.de/i/view/GBR/en/prices/germany/laender-ticket.shtml

In Austria:

http://www.oebb.at/en/Tickets/Groups/Einfach-Raus-Ticket/index.jsp

Just to add to above, check Salzburg - Verona via Innsbruck. In fact I might even suggest Munich - Salzburg - Garmisch / Mittenwald (via Innsbruck) - then back via Innsbruck to Verona

Fully agree with #1, the rail pass makes no sense given your intended itinerary. Consider day trips to either and/or Neuschwanstein (head for Fussen, google Neuschwanstien for info to find out why), or Dachau concentration camp.

Thank you for your help. My question is... if we travel from Munich to Salzburg and then Salzburg to Garmisch, we are traveling from Germany to Austria and back Germany. Would these deals apply in those cases?

The Bayern Laender ticket that #1 referred to will cover you from Munich as far as Salzburg (despite it being across the border) and Garmisch.