Good Spontaneous, Bad Spontaneous

We all want to be the cool, spontaneous traveler who likes to pop into local dives and try their unique food, or dance in an unexpected monsoon. However, a seasoned traveler knows the difference between good spontaneous and bad spontaneous.

Example 1: Bob and Betty wake up in Kauai, and decide spontaneously that they want to go kayaking. They drive an hour to the Wailua River to spend a day on the water. Unfortunately, they slept in, the 6 permitted self-rental kayaks per kayak place are gone, and they didn't book a guided tour, so they end up wandering around town and eating some dry burgers before driving back to their resort, having wasted the best part of the day. This is Bad Spontaneous.

Example 2: Bob and Betty have booked a self-rental kayak in Kauai, and have decided to leave for their kayaking trip early in the morning, as they have read that the crowds are thinner and the kayaking better then. Before they drive up to the Wailua River, they grab a delicious picnic lunch at a local deli so they won't starve while kayaking. They pick up their reserved kayak, hit the river, and after paddling for a while, decide to spontaneously jump into the river while they're kayaking. This is Good Spontaneous. (Also part of our upcoming itinerary).
 
I enjoy having a framework and being spontaneous within that. Trying to make decisions about what to do and where to go eat while we are stressed and starving never ends well for us, so below I've shown our itinerary. I do have a short list of places that sound good to eat, (I hate wasting money on bad food) but food plans and the next day's schedule usually get finalized the night before.

Proposed Kauai Itinerary:

Thursday:
Get in late, explore resort pools and hot tub.
Friday:
Snorkeling, check out other beaches, beach walks by hotel, nap, relaxing in Hawaii, sushi supper, evening luau at Smith's. (Show only).
Saturday:
Kayaking and lunch on the Wailua River
Resort in afternoon ?
Sunday:
Sunday drive to explore island and hiking--Austin still has to pick one--Honopu Ridge, Nualolo, Waimea Canyon, Blue Hole
Monday:
Snorkeling, hit the beach before plane leaves at 12.