If I was gifted with a year of time, enough money in the bank and (this is the tough one) did not have to start over yet again working my way up at a job (the wife would esp appreciate that!!! :) ), I would not do one grand adventure but a series of mini-adventures. Cherry pick trails and routes for the best time of the year. Come back home for a month or so  and then set out again.
January or so? I'd backcountry ski every day or close to it. When I was unemployed a few winters ago, it is without exaggeration to say I was on skis probably 20+ days out of 30 during winter. It may not have been all day affairs (3 hrs perhaps at time), but it was skiing. Nordic backcountry or backcountry tele. I was in the best shape of my life, too. Cardio, core, upper and lower body. Balance. Large and small muscle groups. Plus it is beautiful and fun!!!
Which brings us to:
Starting in mid Feb or early March, I would "thru-ski" the 300 mile long Catamount Trail in Vermont. Always wanted to do it. Logistics (esp camping) may be interesting at times, but what a way to see New England in the winter!
Short rest and then:
early-ish to mid-April: A southwest desert trail. The Hayduke, AZT or GET would all be worthy jaunts. The AZT for the beauty of Arizona, The GET for the wonderfully easy logistics or the HDT for the sheer uniqueness of the Colorado Plateau. Decisions. Decisions.
And in May and June, I would focus on local hikes and work on my climbing more. Enjoy my town and haunt the brew pubs after post-hikes and climbing. :)
In July, time to squeeze in the High Sierra Route.
Early August? Time to hike the Great Divide Trail along the Canadian Rockies ~700 miles of some of the most scenic, stunning and awesome mountains I've ever seen.
Finish by mid-September at the very latest (and hope it does not snow ;) )and go back to my very patient wife.
Spend a month again enjoying the local area as the CO Rockies in late fall is cool, crisp and wonderful.
And in mid October or so, I'd do the Allegheny Trail just as the leaves are hitting their peak foliage. The Eastern hardwood forests are awesomely beautiful in the Fall, and I've always wanted to do this obscure trail. At 300 miles long, a nice two week journey for me.
And in November? It is car camping season in the southwest. Short days, but less people in the BLM area, national parks and national monuments. Makes for long nights in camp..perfect for what I call "base camp" car camping. Make long day hikes, come back to camp and snuggle in the ridiculously large and warm sleeping bags we have. This would be after a delicious meal we cooked on the Coleman stove. Naturally we'll see it on our camp chair in our out-of-the way primitive campsite some where off a dirt road in Utah. We'd enjoy the brilliant night sky above while sipping on a hot drink with "splash of something extra". Mrs Mags likes these types of trips and I've grown to enjoy them myself in the very late fall/early winter.
And in December? A little skiing while I get ready to start another job.
Maybe it is my age, enjoy my community or the fact that I've done some reasonably large adventures earlier in life, but the mini-adventures and cherry picking the best seasons to do them in really appeal to me at this point in my life.
 I actually enjoy where I live. Would not want to be away too long. See above about the wife part. ;)