For a bunch of different reasons I’ve found the original post in this thread to be difficult to answer. Actually, it’s been easier to figure out what I would not want.
With unlimited time off, I see some appeal in extended stays at three or so locations. However, my wife and I appreciate, enjoy, and depend upon our friendships and community too much to want to essentially drop out of both for much of the year.
Even though the question is framed to provoke a fantasy response, I’m not confident we’d know what to do with a $100k annual travel budget. In our international travels, both my wife and I have generally preferred somewhat off-the-beaten-path, modest Airbnb or VRBO rentals, often in neighborhoods, to hotels. We also both prefer a mix of meals that leans more heavily into self-catering and street food than towards fine dining. Both often afford more contact with the local culture. In our 20s and early thirties from the late 80s to the mid-90s, mostly separately, we both did a fair amount of seriously shoestring-budget travel in developing countries (South America for her - Kenya, Egypt, Jordan, Syria, Turkey, and Eastern Europe for me – pre-Chavez Venezuela and some backwaters of the Caribbean together). We’re too old for that kind of travel now, but we both generally enjoy budget-ish travel because we find it's generally a bit less insular. For some of the same reasons, neither my wife nor I (with the exception of cat skiing, I guess) are likely to enjoy most all-inclusive, cruise, or extended-tour scenarios.
Funny to say on FTO, but even indulging in fantasy, I’m not sure I’d spend a huge amount of time skiing every year if I had a larger budget and a lot more time off. I’m really getting to the point that I can’t stand not just the cost, but the hassle factor, of large NA resorts. In other words, even if I had enough time off to make the economics of a multipass work for us, I don’t have much interest in dealing with the crowds and hassles the multipasses have brought to large resorts. In 2024-25 I added four new resorts to my modest list: Silver, Mt. Spokane, 49 Degrees North, and Fernie. Skied all with reasonably good packed-powder conditions, but no recent fresh snow. Honestly, overall, I enjoyed our days at the first three more than my two days at Fernie. I see both myself and us doing more skiing at the mom-and-pop and midsized resorts of the Northern Rockies in the coming years. Japan would certainly be attractive in a fantasy scenario in which I had a lot more time off. With more time off, I also feel like we should ski Europe at least once, but at least right now, I know that the need to hire a guide to safely get off piste would drive me absolutely insane. There might be a bit more cat skiing in my future at some point, but even with a fantasy budget, I would probably take a year or two off from that at this point. If I ever heli-ski, it will have to work out spur of the moment; my psychology will not accommodate down days for weather.
So what would I want to do? Well, our daughter took a trip last summer, when she was 18, that I’m still kind of envious of. She and 6 other young people ages 18-23 got driven over four days with all their gear and provisions to Yellow Knife, NWT where they took a chartered de Havilland Otter floatplane 250 miles east and deep into the bush (140+ miles to the nearest road!) to Lynx Lake, near the Nunavut border. Then, over 38 days, they paddled and portaged about 600 miles down the Thelon River (a mix of swifts, runnable rapids, unrunnable rapids, and huge lakes mostly north of tree line) to the Inuit town of Baker Lake, Nunavut. From there, they caught a commercial flight to Winnipeg, connecting though Rankin Inset on Hudson Bay. (She’d been invited to go on the trip at end of the summer of 2022 and worked hard during her last two years of high school as a nanny, a lifeguard, and a swim instructor to earn money to cover all of her costs for the trip. Chartered floatplane time ain’t cheap!) As long as we’re talking fantasy, I’d love to take such a trip. Returning to reality, however, I understand it is not likely I will ever have the right combination of time and physical stamina such a trip would require. Under the right set of conditions, we might consider a commercial trip for some shorter, less arduous version. With more time off, I’d also like very much like to find the time to take a few perhaps month-long budget-ish trips around India, Southeast Asia, and South America. I know I would appreciate such trips a little more if spread out over at least 2-3 years.
Like a lot of Americans, time is kind of a big issue for my wife and me. Neither of us are in professions where we can have much realistic expectation of more than about a month off a year at any time before retirement. It’s most likely that at least one of us will need to work until 65 to keep us in health insurance. (That is assuming Medicare eligibility remains at 65 and that Medicare is still funded when we hit 65. Both are questionable assumptions, especially the later.)
