I see the appeal of going on a two week boating trip on a large ish sail boat, doing some real sailing and some steering and manning the sails and stuff would be cool and going around some lesser seen islands in the world with a small group of people, stopping off on tropical beaches and the like.
This is the best!
My parents friends rented their house out and bought a boat to sail around the world in, they've been pretty much everywhere I would want to go!
I've been away with them between Greece and Cyprus which was amazing, so much better than any holiday I've ever been on, just being in the ocean, sailing properly, being able to go anywhere you want, theres so many little places people just don't see, all the back street restaurants, anchoring up anywhere and spending the night star gazing (out of this world, no light polution etc) so many little caves we found.
We went to an volcanic island in Greece as well, just rented out some motorbikes and took us the best part of a day to ride up and back down into the volcano, was immense even if it did smell horrendous!
They've been pretty much everywhere, and are going to the Galapagos islands next, I'm going again with them and can't wait.
I go sailing with my old man a lot and hope one day I will be able to do this (when I retire etc) a fair while yet lol.
(Charter holidays would be a good start as well, if you're not into the whole cruise thing)