Fall there is not too crowded, and the water is still warm, days warm to hot, nights pleasantly mild. You can sleep under the stars (no bugs). Call out for echoes in many alcoves. Go swimming and hiking. Relax. It is a place I know I'll miss being (relatively) close to.
If paddling starts to seem like a chore with all the "kit" and need for planning, pick places that have more margin of safety if you don't want to set alarms for your starting time. And avoid places with cold water when you're in that frame of mind. You'll still need to be careful about wind conditions in any body of water that is large.
PFD's (Life Jackets)
Deck Rigging Gear
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