Travel

For travel into unknown territory in the Wilderlands I give a bit of colour, maybe some legends of the vicinity, describe what PCs can see, encounter checks and recently-were-here checks. Encounters I use a 6 on d6, roll a few times a day, then either select from nearest NPCs/monsters or roll on a table. These days I mostly use a d20 table based off donjon prerolled encounters from http://donjon.bin.sh/fantasy/random/...;enc-type=Road - most of those are non hostile encounters and IMO beat the "Manticore jumps out! Bugbears jump out!" approach encouraged by the 1e DMG & MM2 AD&D charts and other monster-heavy charts, though even there using a 2d6 Reaction check can produce something interesting.
I always roll checks in the open, players love/dread seeing that 6 come up with preternatural frequency.

I like to roll weather daily, pretty much given up on weather generators though. I use a d8 so the players know it's not an encounter check; 1 = really bad (or cold, stormy) weather, 8 = really good (or dry, sunny). Also use d8 for direction of wind, 1 = north; may modify if there is an obvious prevailing wind.

I will also use "Indiana Jones red line on the map" approach "3 days later you arrive" at times to abstract travel - almost never in Wilderlands, but in a big largely undetailed world like Forgotten Realms or Greyhawk it can be necessary. I have done it in Wilderlands when I really wanted to skip the road travel between two known locales, but have tended to regret it.

Maps - especially in known territory, but very often otherwise, I usually show players the hex map I'm using, as well a describing what they see. I generally find players are short of info & it helps to give them plenty. I also find the idea of fantasy PCs marking hex maps in-game a bit weird.

http://www.therpgsite.com/showthread.php?38195-Early-Random-Dungeon-Gen-systems-and-Outdoor-Survival&p=1013971&viewfull=1#post1013971