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There's no real "vacationing" in Island Paradise. Boats are basically water transportation that are only practical in Isla Paradiso since that's the only neighborhood with multiple islands not connected with roads. If you want to go to a different island there, you just go there with your boat. Nothing special.
If you live in Isla Paradiso and say, you want to move to a different neighborhood like Sunset Valley, you can use the new move out system. However, if you really move to a different neighborhood, your previous neighborhood data will be completely deleted. Family members that are left behind, friends, and the people there will be deleted and you can't see them again when you move back there. The move system is basically saving your family to the family bin and changing neighborhood.
You can use Twallan's Traveller mod to prevent this, however. You can move to a different neighborhood while still retaining the previous neighborhood's data. Keep in mind that this will cause your save game to bloat since it contains excessive data for multiple neighborhoods, though.
Just call me Nikel