I've already got Windspear/Umar Hills on my map, but I can't seem to access either. Both are outlined in gray. What am I doing wrong?

PS: I have done the De'Arnise keep quest, so I've gone through the city gates.

To "activate" Windspear, you just need to talk to Jordan Firkraag in the Copper Coronet & accept his offer to clear out some monsters. If you declined his offer, you may be screwed, unless you're a Paladin - visit the Radiant Heart in the Temple District (if you're still unable to reach Windspear [or Umar, see below], you can teleport there, but that's a whole 'nother ballgame).

Umar Hills can be activated in a couple of ways. Delon (I think his name is) at the City Gates should recruit you to this one. Again, you must say "Yes, I'll help you" (or something to that effect). IIRC, Delon will find you in the city if you have Minsc in your party even if you don't go to the gates. Alternatively, you can talk to Tolgerias (sp?) in the Government District, in the Council of Six building (in the middle of the map) to activate the Umar Hills.
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mild spoiler
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...in that I mention Valygar here... I believe you can also go to Valygar's Home (which is labelled on The Docks map) & ask his butler where he is, although you may have to have already talked to Tolgerias to have his butler appear - I'm not quite sure.

In any case, any of those should activate Umar Hills.

The other thing to remember is that, if you didn't have those places activated, then got them activated through one of the dialogues, you will likely have to exit through the City Gates again, even if you have already exited from the City Gates, in order to reach them.

- Imrahil

<font color="gold">Imrahil is correct, you'll need to exit through the City Gates the first time you travel otside the city. ;)

And a little nitpck on Imrahil, Flydian, the guy who tells you about Trademeet, is found in the City Gates. Delon is found in the Government District. ;) </font>

actually I had delon camped out in front of the copper coronet in one game, although I think maybe that was because he started chasing us, but I exited the gov't area before he could start talking, and so followed us to the slums.

ps. you don't need minsc to activate delon, minsc just has dialogue with him if he's in your party. AFAIK you never need have any NPC in your party to activate major areas, talking to the right person will open them up reguardless of who is in your party (otherwise soloers wouldn't get far)

Exiting the city through the Gates doesn't allow you access to ALL map areas--it only allows you access to the areas that are already on your map. If you add a new area to your map, it will appear in gray, and to turn it blue, you must exit via the Gate, even if you have done so previously.

That's it! No "activations" of areas are needed. The areas either are on your map or they are not there. Once they are on your map, you can access them without any additional action.

But, when you travel to a new area FOR THE FIRST TIME, you must go through the City Gates in Akathla. The new area is unaccesible from elsewhere and it will be greyed on your map if you attempt to travel to a new area without going through the City Gates. Once you have already visited the area, you can travel there repeatedly from anywhere.

There are few exceptions from this rule:
- You can travel to the Ruined Temple from Umar Hills directly - after getting the quest, i.e., after the area appears on your map.
- You can travel to the Druid Grove from Trademeet directly - after getting the quest, i.e., after the area appears on your map.