My thoughts on your post - well you did ask

Having ridden Canada to Patagonia recently I would say 3 months is not long enough for such a trip to catch your breath and look around.

Alaska is beautiful wilderness and I love that stuff now but when I was a younger traveller I wanted a bit of life and culture.

So I reckon a combination of wilderness, culture/action, exotic destination and holiday time would make the perfect first trip for a family - something for everyone.

My option would be ride down the Appalachian MABDR (wilderness plus lots of iconic routes such as Skyway, dragons tail etc), down to New Orleans (culture), then down into Mexico (exotic) If you go down the east side (not the coast) you’ll come across very few non-Mexican tourists and be in the real Mexico. There are beautiful mountains with waterfalls and Cenotes without the crowds. head down to Oaxaca for food and cool beaches then if you still want a bit of main steam holiday head for Yucatan.

Back via the west route - I’m sure I don’t have to list the stuff to see on the way back.

If I hadn’t already done most of this I’d be planning a trip now

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.

As markharf suggests, there really are too many variables to consider at what is still the embryonic stage of planning such a huge trip.

fwiw. [as Mark suggests] I'd get a bike for each of you (which suits the size/strength and experience of the respective rider) and plan a shorter cross-country style trip or two next year in and around the United States - Colorado and Utah for example, or Montana/Idaho/Washington, or even south to New Mexico & Arizona - and basically get a feel for what it's like travelling as a [family] group on individual machines.

Not only will you all gain valuable experience (both as individuals and as a group), but you'll soon know what it is you don't like about travelling/the bikes you've chosen just as much as the things you do...

And if you're still all in agreement, then spend next winter planning your 2025/26 'big' trip.

Jx

ps. there is also a huge difference between a One month trip and a Three month trip with regard to where you can go, and whether you fly/rent or buy/ride your bikes - again, this ought to become clearer after a couple of shorter trips next spring/summer.

Yeah, we're definitely assembling a set of machines and doing some test trips!

Very fun idea, thanks!