scalaz can be of help here. You'll need scalaz-contrib which adds a monad instance for Try, then you can use OptionT which has nice combinators. Here is an example:
import scalaz.OptionT
import scalaz.contrib.std.utilTry._
import scala.util.Try
def method1: OptionT[Try, String] = OptionT(Try(Some("method1")))
def method2: OptionT[Try, String] = OptionT(Try(Some("method2")))
def method3: OptionT[Try, String] = { println("method 3 is never called") ; OptionT(Try(Some("method3"))) }
def method4: OptionT[Try, String] = OptionT(Try(None))
def method5: OptionT[Try, String] = OptionT(Try(throw new Exception("fail")))
println((method1 orElse method2 orElse method3).run) // Success(Some(method1))
println((method4 orElse method2 orElse method3).run) // Success(Some(method2))
println((method5 orElse method2 orElse method3).run) // Failure(java.lang.Exception: fail)