By road, Yartar to Xantharl's Keep is about 520 miles.  Do you all want to travel at a normal pace?  Do you want to stop anywhere along the way?

Make a Perception roll for the first few days.

Make a forage survival roll if you are foraging?

Ireniana Perception rolls 

18

16

21

Survival for foraging

15

( Normal pace. By Road. Try to sleep in towns if possible...if not then roadside camp.

Perception: 13

Perception: 7

Perception: 14

Use Rations. )

Whistler Perception: 21
Whistler Perception: 18
Whistler Perception: 17
Whistler Survival: 9

Owlbear Perception: 7
Owlbear Perception: 15
Owlbear Perception: 19
Owlbear Survival: 10

(Yep, normal pace, sleep in towns when possible)

Perception: 18

Perception: 18

Perception: 14

Survival: 5

Dang, everyone is sharp eyed!  Foraging works as well.

The three day stretch from Yartar to Triboar is uneventful.  There's less travelers than usual, in fact.

Upon your triumphant return to Triboar, you are all greeted warmly by Darathra, who is anxious to hear if you delivered her message and excited to hear about the rest of your adventure when you tell her.

The carnage in Triboar has been cleaned up, and repairs are well underway.

At the behest of Urgala, you spend the night for free in her inn, and the morning of the 3rd of Eliant start the journey north.

(Pick up any supplies needed in Triboar.  Droop tops off his rations, in the form of hard boiled eggs.)

Asking around in Triboar about the journey north, you hear that Longsaddle is a small, sleepy frontier village and member of the Lord's Alliance.  The Gilded Horseshoe is the place to stay.

It's a 7 to 8 day journey to the next town, LongSaddle.  For this week long journey, make just 1 perception check, and if you are foraging, a Survival check at disadvantage for normal pace

Ireniana Perception 24

Survival - 15

Whistler Perception: 20
Whistler Survival: 11

Owlbear Perception: 17
Owlbear Survival: 5

Baeshra perception: 22 Survival: 10

Perception: 10

The week-long scenic route from Triboar to Longsaddle also passes uneventfully.   Food is pretty easy to forage on this stretch, and ironically, Owlbear is the only one who was unable to feed himself off the land.

It's evening of the 9th of Eleint, as the dog days of summer drag on, but it does start to cool down a bit as you get closer to Longsaddle.

Rows of homes and businesses stand on either side of the road, other than that Longsaddle looks pretty small, and quiet.

On your way to spend the night at the Gilded Horseshoe Inn, you see several wanted posters, all bearing a charcola sketch of a dwarf with dark hair and a mad gaze.  Written on them in common:

“Let justice be done! The Marchion of Mirabar hereby offers 5,000 gold pieces for the capture of the brigand Worvil Forkbeard, known from Luskan to Mirabar as the Weevil. Last seen around the Mines of Mirabar, the Weevil is wanted for theft and murder. He is armed and dangerous. Deliver him to the Axe of Mirabar to receive payment.”

The Gilded Horseshoe Inn is surprisingly nice and well kept.  An evening of drinks, dinner and rest will cost the whole party 8 gold.

Alright, make another Perception check, and DC12 survival roll at disadvantage() for foraging for the 4 days from Longsaddle to Xantharl's Keep.  If you don't make it, or don't want to forage, consume 4 rations.

If you want, make a DC15 History check to see what you know for Xantharl's Keep:

 DC20 History check:

Map from Triboar to Mirabar:

While happy you walk at the start of the long trip, by the end Nyx sits on the back of the wagon playing tunes and making images of Whistler running after some fire giants with a sword double the size of the little Kenku.

"I think from what I have heared about this place, its run by Narbeck Horn and it truly is a keep. More guards around here then bees to a pot of honey and double all the common folk. We could make some money here, soldiers are always wanting entertainment and have more money than they can spend."

OCC:

Perception 21

History 23

 Whistler reverts to a Chick, watching and demanding an encore from Nyx.

Umbriel Perception: 8

Survival: 4

History: 4

Along the way, Umbriel tells Droop of his homeland in the Shadowfell, and of the many dangerous denizens there. In response to Droop's questions, he's not sure if balhannoths are edible, but he promises that if he ever finds out, he'll save some for Droop.

Haha!  Droop listens attentively, asking all sorts of questions about how those things would taste.

Droop Perception: 3

Droop Survival: 8.

Baeshra wanders along with the others, at some point he'll realize something, "So this person we're turning in, do we need to capture him, or just verify its him and let the guard do it? And does he need to be alive for it?" 

Perception: 25
Survival: 12

"I think we should check with Narbeck but I imagine for that much coin, it's a dead or alive situation. And seeing he's wanted for thief and murder, he can probably defend himself. No way he's going to come along because we ask"

"I'll do an encore later tonight Whistler" she adds, ruffling the feathers on his head.

Perception:8

Survival:16

History:10

" This fellow is giving dwarves a bad name....we should probably teach him some manners."

The hot weather breaks and turns to rain on the evening of the second day, and it continues for the next day and a half to Xantharl's Keep.

The third day passes in the rain, and on the late afternoon of the 4th day Xantharl's Keep comes into view.  A tall outer wall circles several dozen narrow stone houses and a few businesses.  The only inn appears to be the Falling Orc inn.

A hulking female half-ogre greets you from behind the counter of the inn.  "Hi!  I'm Arzastra.  You look wet and tired!  Come, warm by fire!" and she points to a roaring fire in a soot stained fireplace.

"How many room?  1 gold each room.  Good food too."

Ireniana will toss a gold. "I'll take a room."