I totally agree with Gilrohir.
It is worth to point out one more thing - even if wanderer has a "safe-house" in every land along the route, stopping in each one of them wouln't be such a good idea.
-You have to begin new journey after every long rest, rolling for embarkation (sometimes starting in Severe or Daunting terrain, which increase chances for low Embarkation roll.).
-Even if the journeys will be short, each of them is another d2 events (with additional +1/+2 if the journey starts in more difficult terrain). More events = bigger chance for failed Event rolls and their consequences (Shadow Points, Fatigue etc.). Sometimes is better to take longer route, without long rest after every minor leg of a journey.
Remember also, that each time the company ends its journey (this includes wanderer's "hideout"), Guide has to make Arrival Roll. If the destination (in this case "hideout") is in Hard or Severe Terrain, it suffers -1 modifier, if in Daunting it has -2 to roll. Given the fact, that every roll 4 or less have some drawback for the characters, the more arrival rolls you are making, the risk of getting extra Shadow Points and Fatigue at the end of journey is greater. So yes, the players have to decide if they want to take the long rest (and regain hit dices, class abilities etc.) in some "relatively" safe place, risking that the world, danger and Shadow will take their toll on them anyway.
If you want to play the "grim and gritty" version, you could rule that Arrival Roll after ending journey in Wanderer's "hideouts" are made with d6 instead of d8 (because they are "emergency safe-places" without any conveniences), but be prepared that could end very badly for the characters.
Hope it will help