So, I did guess that WI was somewhere in the USA and not West Indies : )
Lots of good thoughts from others; my reactions:
Ride from WI to Chile.
- this would take us at least a year - 3 months is not nearly enough if you plan to see anything.
Fly to South America (Colombia?), ride around South America, sell the bikes (back in Colombia or ???), fly home.
- same comment - it took us 11 months to travel "around South America" and we had already made a lot of trips in SA, have done lots since then in SA, and live in SA.
Ride and camp from WI to Alaska (likely sell bikes once we arrive and fly home).
- you could probably do this in 3 months, although I'd think that double this would be better. We wandered around Western Canada (BC, Yukon, NWT, and a little bit of Alberta) for 3-1/2 months last year and didn't touch the USA, so it would take us at least twice that to do the WI-AK trip.
Ride from WI and camp in national parks of the Rockies and West Coast
- see above comments.
The point I am seeking to make is that you could do some or all of the trips you're considering, but will not see a lot, in my opinion. If your goal is to ride through interesting country and not spend any time getting to know the towns, taking hikes, etc., then things are easier.
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