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Most tyre pumps have a built in gauge, so it won't be absolutely necessary to carry a gauge. All Royal Enfields are air cooled, so you won't need a coolant, which are meant only for liquid cooled bikes. As far as Engine oil is concerned, you should first start from Chennai after getting it topped up at your service center/mechanic. You can take some spare oil in a small bottle, and use the dipstick during the ride to check the oil levels.

On the Royal Enfield, there are only a few things which would normally bug you during a long ride, that too on rare occasions.

1) Flat tyre (ask your mechanic to give you a demo and you can learn to do it yourself, including how to use the puncture repair kit.)
2) Blown fuses ( carry a few spare bulbs)
3) Broken throttle and clutch wires - again, first take the cable out and practice putting it back again. Again, you can go to your mechanic and learn how to.


Apart from your list of tools, carry a pair of pliers, scissors, spare piece of wire. Would be great if you can also carry an adjustable wrench if you can find one. Saves you the trouble of carrying multiple spanners, especially in bigger sizes (14+)

Make sure you and your wife wear a properly strapped on helmet, gloves and a riding jacket if possible!

Have fun - Gingee fort is awesome! I have not stayed in Yelagiri, but my outlook traveller weekend guide recommends Hotel Hills, Taj Garden resorts, Hotel Yelagiri and Hotel Nigress. Maybe you can check them up on the net.