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2 pax travelling and travel plans -  15 Oct 09 from Zurich-Interlaken. 17/10/09 Interlaken-Milano, 18 Oct 09 from Milan-Rome;  19/10/09 Rome-Civitavecchial; 30/10/09 Civitavechhial-Piza and from Piza-Firenze, 31/10/09 Firenze-Bologna-Milano; 1/11/09 from Milan-Brig; 3/11/09 Brig-Geneva-Bern-Geneva, 4/11/09 Geneva-Zurich.

For such travel plans, is it better we buy a Eurailpass before leaving home?  Or can we get better priced tickets along the way?

In your situation a number of solutions are possible, but neither of them includes Eurail Pass (for such trip it is a rip off and absolutely unnecessary):
1) If you want to simplify whole ticket thing as much as possible go with straight forward International ticket (TCV tariff) for the whole route Zuerich-Interlaken-Milano-Rome (will cost app. 100 euro per person). It works like a railway pass, but for certain route - you just get off train and hope in as many times as you like on your way. But be sure to specify exactly the route you want to use while purchasing it. Domestic Italian tickets like Rome-Civitavecchia, Pisa-Florence etc. cost quite cheap, so no need of any pass for Italy (check our Italy page for some ideas on types of trains and tariffs)
2) Unfortunately SBB canceled Promo e-tickets for domestic trips in Switzerland, so there is no easy way left to save some money (usual Half-fare card useful only if you travel a lot in Switzerland). So probably a good choice for you will be to purchase Swiss flexi pass for your domestic travels in Switzerland (flexi needed because of before and after Italy parts of your journey) - http://www.swisstravelsystem.ch/index.php?id=131&L=1
I guess 4 days within one month will work good enough. In order to get from Switzerland to Italy cheaply you either use you pass till Swiss-Italy border + combine it with cheap domestic Italian tickets. Or look for SBB's Click and Rail offer (https://www.sbb.ch/mct/wi/shop/b2c/adw.do?6056)
3) Another option is to use regular SBB domestic tickets for you Zuerich-Interlaken part and Swiss pass for your Swiss-Italian border -"3/11/09 Brig-Geneva-Bern-Geneva, 4/11/09 Geneva-Zurich." part. Because that second part of you Swiss journeys includes quite a lot of train ride, so pass will be probably the best option for it.     

Hi Thanks for the advice  It doesn't looks easy to connect and guess it's because we are not very familar with the rail systems in Europe.  Can we get the TCV tariff tickets from Zurich and must we specify all the routes that we are going to take to the ticket staff?

Regards

Can we get the TCV tariff tickets from Zurich and must we specify all the routes that we are going to take to the ticket staff?

Yes, you should be able easily purchase regular TCV tariff international ticket in Zuerich. But as was said earlier - make sure you specify very precisely the route you want to take and type of the ticket you need. For your way back it is as well possible to use such kind of a ticket, but it makes sense only for Florence(Milan)-Brig-Geneva part, rest of your travels in Switzerland should be done either with Swiss domestic tickets or Swiss pass. But remember that using TCV ticket for your return part of the journey will be more expensive than combination of Italian domestic tickets + Swiss domestic (Swiss pass) - such way is usually called - "breaking" your tickets via border.   

Good news came from SBB just recently - company once again offers SuperSaver promo e-tickets for major Swiss rail routes (more info on our Swiss page or SBB web page - https://www.sbb.ch/mct/wi/shop/b2c/adw.do?4004). So you might as well consider such option too.