Swiss half off pass
 

If I go from Germany through Switzerland to Italy and back to Switzeralnd does the "Swiss half off pass" work at all? I'm traveling to Switzerland for two weeks in the summer. I wanted to go to Germany first for two days and then travel through Switzerland to go to Italy for a couple days and then come back to Switzerland (Zermat) for two weeks all via train.

It's a couple of years since I used the Half Fare card but basically any ticket you buy for travel in Switzerland is half price. You have to buy an additional ticket for the German/Italy portion of your travel.

Sorry, what I meant to say is that the German/Italy portion will be charged at full price (or whatever discount you can get for those countries), not that you necessarily need a separate ticket.

From where in Germany to where in italy?
Low cost flights may be cheaper than trains (even if you get half fare in Swiwtzerland).
The half fare card will most probably make sense. The full train fare from the Italian border to Zermatt is 54 CHF and you will have to pay at least the same amount if you go back to the border or to an airport. Add to that the Gornergrat railway fare of 82 CHF and you arrive at 136 CHF without and 188 CHF with Half fare card. If you spend at least 52 CHF for other mountain railways or for other journeys in Switzerland, the half fare card makes sense.
http://www.swisstravelsystem.com/en/...e-card-en.html
https://www.sbb.ch/ticketshop/b2c/sprache.do?en

I'm going to visit a friend in Landstuhl germany, which mean I will fly into Frankfurt. Then do the Cinque Terre in Italy, even though I would love to see more of Italy that's probably one of the neatest places to go as a hiker. Then I will be meeting 5 girlfriends in Zermat, Switzerland.

My suggestion:
Fly with http://www.ryanair.com/ from Hahn to Pisa; fares start at 67 EUR (with 1 piece of checked in luggage). I suppose your friend can drive you from Landstuhl to Hahn airport (88 km). By public transport, it's much longer as you will have to make tons of detours.
Timetable for Monday, Wednesday, Friday (other times at other days):
Landstuhl dp 15.06 - Hahn airport ar 18.18, change at Kaiserslautern, Munster, Idar Oberstein.
Ryanair: Hahn dp 19.55 - Pisa ar 21.30.
Italian railways: Pisa airport dp 22.20 - Monterosso (5Terre) ar 0.23, change at Pisa Centrale. Train fare Pisa airport - Monterosso: 12 EUR

If you do all by train, you have to leave Landstuhl at 8.15 and will arrive at Monterosso at 21.03
Discounted fare up to Basel if you book well in advance in the web:
39 EUR, Standard fare 69 EUR
Basel - Domodossola with Swiss half fare card: 36 EUR
Domodossola - Montrosso: discounted web fare 38 EUR, standard fare 49 EUR

Best connection Monterosso - Zermatt:
Monterosso dp 14.55 - Zermatt ar 22.13, change at Milano Centrale and Brig.

In July, 5Terre will be overrun by tourists from overseas. Among the crowds staying in the 5 tiny villages, it may not be impossible to find some Italian people, however.

If a round trip flight to Frankfurt is much cheaper than a multi leg flight, go back to Frankfurt. Otherwise check the possibility to fly back from Milan Malpensa, Zurich or Geneva.

This information has been really helpful. But now I'm thinking I would like to arrive on August 20th to do Cinque Terre and Ryanair doesn't fly that day. I was trying to look up the trains and prices you have here but I couldn't figure out which site you used and the prices I found were way off.

My brain is going fuzzy. I'm trying to think what I could do with myself if I arrived on the 19th by air. I even thought of going to venice for a day but that would be too much too fast, and I probably wouldn't be that impressed, lol.

August 20th with ryanair:
Hahn dp 6.30am - Bergamo ar 7.50, 82 EUR
Train: Bergamo dp 10.57 - Monterosso ar 15.02, change at Milan, 31 EUR http://orario.trenitalia.com

Better solution: Hahn dp 19th August 20.05 with ryanair, Pisa ar 21.40. Sleep at Pisa.

Train fares Germany: https://www.bahn.de/i/view/DEU/en/index.shtml
Train fares Switzerland: http://fahrplan.sbb.ch/bin/query.exe/en

If you have a spare day at Pisa, you may visit Pisa, Florence, Lucca, Volterra, Siena, Elba Island ......