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I'm currently running Tomb of Annihilation for the first time and have a bit of an odd ask. I'm mainly asking this because one of my players is running a character who's really into maps and wanting to map the island.

If the party succeeds on a proper navigation check for the day and I clear one of the hexes on the map, then say they want to go back exactly the way they came... Do I still need them or their guide to roll a navigation check? Or is that only for when they move into new hexes?

If the player characters have the map from Syndra Silvane and are trying to fill it in too, does that help them with checks at all?

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These hexes are big!

The scale on the map is 10 miles (16km) across a hexagon. This is 86.6 square miles (221.7 km2). For comparison, that's 25% larger than Washington DC.

You say your characters spent 1 day crossing this area on foot. Realistically, they know next to nothing about it. It is entirely possible to run an entire campaign from 1st to 20th level entirely within an area this big.

For a further idea of scale, Chult is bigger than Great Britain and Ireland:

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Aproximately 71 million people live on those two real world land masses but the area is still over 80% rural or wilderness. The current record for going from one end to the other of Britain on foot is 12 days, 11 hours, 6 minutes and 7 seconds but that was on roads and not through jungle.

To answer the headline question:

If you are familiar with an area you don’t need Navigation but your character’s aren’t.

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I would let them roll but since they have map and it is somewhat familiar terrain I would give them advantage and/or lower the difficulty. It should not be as difficult as trying to navigate in completely unknown terrain but on the other hand I can imagine perfectly fine that someone can lost when they want to go back where there come from (especially when they did go through that terrain just once).

But the most important question is: Would it be fun for you and your players?

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    \$\begingroup\$ Welcome to the site! We prefer answers like this to dive a bit deeper into the processes you've used in the past. Demonstrate your expertise as answerer by elaborating on your experience when you "let them roll", and how you've helped make it "fun for you and your players". \$\endgroup\$
    – David Coffron
    Commented Dec 10, 2020 at 16:10

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