Games like The Florida Trail
Games like The Florida Trail include Reventure, The Henry Stickmin Collection, Undertale, Late Shift, and Terraria. We matched them by the tags players give The Florida Trail on Steam (Choose Your Own Adventure, Interactive Fiction, Adventure, 2D, and Dark Humor): closest matches first, and among equally close ones the better-known games.

Reventure
Shared: Adventure · 2D · Multiple Endings

The Henry Stickmin Collection
Shared: Choose Your Own Adventure · Multiple Endings · Choices Matter

Undertale
Shared: Choices Matter · Multiple Endings · Pixel Graphics

Late Shift
Shared: Choose Your Own Adventure · Interactive Fiction · Choices Matter

Terraria
Shared: 2D · Adventure · Survival

Endless Monday: Dreams and Deadlines
Shared: Choose Your Own Adventure · Interactive Fiction · Choices Matter

Kindergarten 3
Shared: Choose Your Own Adventure · Dark Humor · Interactive Fiction

Roadwarden
Shared: Adventure · Interactive Fiction · Choose Your Own Adventure

To the Moon
Shared: Adventure · Interactive Fiction · Pixel Graphics

The Test
Shared: Choose Your Own Adventure · Multiple Endings · Pixel Graphics

Suzerain
Shared: Choose Your Own Adventure · Interactive Fiction · Choices Matter

60 Seconds! Reatomized
Shared: Choose Your Own Adventure · 2D · Dark Humor

Refind Self: The Personality Test Game
Shared: Interactive Fiction · Adventure · Choose Your Own Adventure

OneShot
Shared: Pixel Graphics · Adventure · Choices Matter

Finding Paradise
Shared: Adventure · 2D · Pixel Graphics

Far Away
Shared: Choose Your Own Adventure · Choices Matter · Adventure

There Is No Game: Wrong Dimension
Shared: Adventure · Pixel Graphics · Indie

Until Dawn™
Shared: Choose Your Own Adventure · Adventure · Choices Matter

Forager
Shared: Pixel Graphics · 2D · Adventure

Beat Cop
Shared: Adventure · Pixel Graphics · Indie

Kindergarten 2
Shared: Adventure · Pixel Graphics · Dark Humor

The Wolf Among Us
Shared: Adventure · Choose Your Own Adventure · Choices Matter

Road 96
Shared: Adventure · Choices Matter · Choose Your Own Adventure

Ten Trials of Babel: The Doppelganger Maze
Shared: Choose Your Own Adventure · Multiple Endings · Adventure