Improved: the Lock & Bridge Planner plans a long run as days
A run longer than a day is now a list of days — each cut at a real overnight stop, every lock and bridge checked on the day you actually reach it. Hammond to Green Turtle Bay is 14 days at 8 hours a day, and the planner says so, day by day.

Days, not one long night

Tools → Lock & Bridge Planner. When your run does not fit in a day, a row of day chips appears under the controls: "Day 1 · Mon, Sep 21 — Hammond Marina → Joliet City Dock · 37 nm · 2 locks · 6 bridges · leave 7:30 AM · in 2:22 PM". Tap a day and the page below is that day: its map, its staircase, its locks and bridges in order, its cards. On a phone the chips stack and the day you tap opens under its chip.
Every gate on its own day

Wilkins Lock on the Tenn-Tom is closed through October 10. Leave Green Turtle Bay for Demopolis on September 21 at 8 hours a day and you reach it Friday September 25 — so the plan holds the boat at Little Island, one red chip per day, until the lock opens on October 11, and the days after it carry on from there. No day is planned through a gate that is shut on that day.
Two ways on

The verdict at the top says it plainly: "Wilkins Lock is closed when you reach it Fri, Sep 25 (day 5) — it opens Oct 11. Two ways." Wait for it — sixteen held days, arriving Wednesday October 14 at 1:06 PM — or go round it by the Tennessee, the Ohio and the Mississippi: 1,162 nm, arriving Sunday October 11. One tap plans the days the other way.
You own the mornings and the nights

"Hours a day" (your boat profile's figure) decides the cut; a day never plans past sunset unless you leave late on purpose. Each day's card has "Leave at" and "Ends at" — pick a different marina or anchorage from the ones near the cut, and the days after it re-plan; the days before it stand. Nothing is written to your trip: the plan lives in the link.
Where to find it
Tools → Lock & Bridge Planner. Pick any two places with Change, or let it take your trip's next leg. It needs an active trip: the plan runs on your boat's speed, air draft and hours a day.