So I'm confident that the wife and I can do the cruising thing in our 40s and 50s. We've got plenty of friends to bring along for ocean passages. Our initial plan is for 3 years and then reassess.
Like I said, I was half-way joking. Sounds like you have more experience than many that successfully pull off the lifestyle. There always seemed to be thresholds that people would reach and wouldn't continue out of fear or funding or just lack of interest. Georgetown, Exuma was always the first one in the Caribbean. The herd would thin drastically making the jump to outer-islands and then T&C, Hispaniola, PR, and the Virgins (and beyond). Getting through the canal also seems to be another stopping point, as things get more serious on the Pacific side.
It does seem like the farther you want to go, the more expenses increase, at least initially. Go outer-island and a wind generator makes sense, plus a SSB and modem (or sat phone nowadays if that's your jam). A primary and backup helm system are a must for open ocean sailing. Go to the Pacific and a water maker is a necessity. Radar is super helpful in Europe. AIS just makes life easier everywhere. And so on...
I lived aboard a Pearson 36 for about a year and some change after college.
Sweet. My parents had a 424 that they circumnavigated the Caribbean with, then crossed to Europe and did the UK and the Med. They eventually made it to the South Pacific and Australia where they sold the boat. Those are great boats and she held up great for them.
As an aside, they were about 2 weeks ahead of us on my last deployment. I got them on HF one day for about 2 seconds, but otherwise we couldn't quite catch up with them due to our tasking. By the time we made it down towards the Galapagos, they had already jumped off for the crossing, so I was never able to VID them and say hi on the VHF.
Why anyone would sail anywhere west of the Seychelles is beyond me. Go south, then take the southern route to Zanzibar if you really want to go. But sailing anywhere near East Africa is a dice roll I'm not willing to take.
Agreed. Over time, there's always places to avoid as a cruiser, be it known piracy or armed conflict. East Africa during that time sounds like a very British thing to do.