I used to share a yacht with my brother in Weymouth- Nicholson 35. It was great fun too, except for the British weather. We alway had big plans to sail it across the atlantic to St Lucia - my brother did eventually but there were also years when the weather was so !!!!!e that I only sailed it for 3 hours in a whole season. He's the captain of an offshore diving vessel so I used to mainly sail with him (as he knew what he was doing!) though I did do the Yachtmaster theoretical stuff. Then he had kids, and I got into flying so we sold her.
I'd vote for flying, and then charting in the sun if you get the sailing urge!