This may not work at all, but Alaska Airlines had round trip flights from my tiny airport near Bend, OR (Redmond) for under $500 to Havana, so I'm giving it a go.
Very tentative plan is to buy/rent a cheap bike in Havana and take minor roads to Vinales climbing location about 200 km away. Will probably bring sport climbing gear and maybe a tiny trad rack.
I bikepacked on dirt roads and single track in Patagonia for a couple months, so hopefully this trip will be a success too!
Bikes were a pretty valuable commodity in Cuba, and often in rough shape. If you could get together a cheap bike I would suggest bringing your own, especially if you plan on doing all your travels by bike. It would be a blast to have a bike around Vinalles, and you could probably make it to the beach in a half day.
Also, if you meet a particularly friendly Cuban (very good chance of this), you could leave them your bike out of good will or for trade. A bike that you pieced together in the states would be worth its weight in gold there.
I'll second the bike comment. I thought I'd be able to just cruise down there and rent or buy a bike for cheap...nope. After three days in viñales i finally talked somebody out of an absolute beater for $40. Bent rims, barely functional brakes, broken pedal, seat falling off. I speak almost fluent spanish and have lived in a couple central american countries for what that is worth. This was 8ish years ago, so I'm sure things have changed a bit. Just be ready for that to be a greater challenge than you'd expect.
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