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What's the longest duration (actual travel, not waiting for connections), longest distance, or most expensive, trip that's available for free once 8 trips have been taken on an opal card?

A trip starting or finishing at one of the Sydney airport train stations doesn't count, because the free travel after 8 trips doesn't cover this.

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Without getting into the philosophical paradoxes inherent in asking about "the most expensive free trip", I'm pretty sure the longest duration & distance that you can pull off with an Opal card in a single day without backtracking is Goulburn, NSW to Scone, NSW by train:

https://goo.gl/maps/6nYEY2oTjqT2

This clocks in at a cool 513.54 km per the official fare/distance calculator and would take you just short of 8 hours (7h 57min, to be precise) with a single connection at Central.

Farewise, though, any distance beyond 65 km is charged the same, so it's just $8.30 for the whole trip. Since Opal cards max out at $15/day, it's not possible to get more financial benefit than this out of any itinerary. Because you're charged every time you transfer, it's quite easy to hit the $15 mark, even on much shorter journeys (say, Circular Quay-Manly return at $14.36 plus any trip anywhere).

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