As you stand and discuss the situation Captain Aragorn approaches.  "We'll be ready to sail within the hour.  Will you be goin' with us?"  He asks.   When you explain that Griggle is seeking passage somewhere else he accepts payment from Griggle.  He waves a couple of crew members to help with the chests and they bring Griggle aboard.

Listening to the conversation Aragorn can't help but add his thoughts.  "Aye, I've heard the same.  I had hopes to sail clear round to Ironmaster but the Sea of Moving Ice is colder than I've ever seen and its locked up tight.  She may be the Icebreaker by name but there's only so much she can go through.  If your job is looking for trouble, the the Dale is where you'll likely find it.  Strange things amiss is what I hear.  You best be be going overland and taking the Ten Trail into Icewind Dale."

Kalannai answers, "I know little.  Not much news is coming out of the north lately.  A pass leads through the western mountains into the Spine of the World, though the route is nigh impassable in winter because of the snow and ice. Well-armed caravans use the Ten Trail to move goods to and from the settlements of Icewind Dale.  But they've slowed to a trickle or stopped completely.  Rumor is the winter is harder and earlier than ever.  You may learn more in Hundelstone, which is on the way.  For most people, Hundelstone is either the last outpost of civilization before taking the pass north to Icewind Dale or the first welcome sign of refuge after making the wearying trip back. But few are even coming from Hundlestone"

Kazri listens to both captain Aragorn and Kalannai. "Very well. It seems that we do not have much of a choice. We do not want to endanger your ship captain Aragorn. We are already grateful for taking us this far. Please give us a moment o discuss the matter."

Kazri turns to her companions. "It looks like we have a long, and cold trek ahead of us. Does the Fellowship of the White Cloaks travel north?"

"Sounds that way..." Chip would reply as he plays with the ring on his finger. "Sounds like it might get a little chilly... I suppose we better make sure everyone is prepared for some cold nights ahead.."

Rhogar had waved off the coin meant for him, wanting to keep the splits even as possible, and trusting there would be other opportunities. The rest he observed quietly and without interruption. Though the more the Bronze heard, the more troubled the expression. Yet at Kazri's questioning, Rhogar pushed aside concern for a grin. "While the sentiment is appreciated, did you need even ask?" He jokingly questions in return. "Let's stock up on what we can here, and set off as soon as possible. For if its possible the route to close, every moment shall count."

He looks to Kalannai on that note and asks, "Where might we acquire supplies in town, and are is there anything you'd recommend we acquire given the circumstances beyond just thick clothing?"

Rekuberk listens and crosses his arms as he looks to the others. "Some of us will have an easier time since we still have the things aquired in our last quest. I will do my best to deal with the snow but after months of being in the keep where it snowed so much I was happy to be away from it..."

Chill rubs his hands together.  "Colder and darker eh?  Sounds fun.  But as Rhogar said, we are already in, so I'm up for it Kazri.  I packed my cold gear the gnomes gave us.  Beyond making sure I can light a fire and stay warm I can't think of anything specific besides maybe some more food.  But that hasn't been an issue up till now. "

Krom listens to Kazri and smiling replies "We already all agreed to follow you on this quest lass, so of course we will travel North. Snow and ice have not stopped us before, they will not stop us now, do not worry."
"We should already have all that we need for our travel, but do not forget that I can craft things as we travel. As Chill said as long as we have food we will be fine."
"Thanks to the jug and the tankard that our friend Rhogar made, we will have plenty to drink to keep us warm."  says Krom with a big grin. "I am ready to go as soon as you all are ready."
Krom turns towards Captain Aragorn "Thank you for the hospitality Captain, safe travels."

Kalannai answers Rhogar,

"There is a trading post near the docks where basic supplies can be bought.  Your travel to Hundelstone will be hard but you seem a capable lot.  What perils lie north of Hundelstone I cannot say. You will need to travel on foot from here, the trail is becoming impassable by anything but foot."

"I can pitch in some coin for some additional food" Chip would say looking to Krom

"Very well. Perhaps we should reset for the day, and start our journey on the next day." Kazri prepares to retrieve her personal belongings from the Icebreaker.

Both Gorrah and Rhogar grinned softly at Krom's comment, but aren't given long to bask long in the warm words without backing turned back to Kalannai. "Ah, I see. Things have already reached that point. Very well then. And thank you for the assistance, Lady Kalannai." He gives a small, informal bow, before then looking to the rest.

"That... if that is what is wished. Considering how bad it's already gotten, every bit of preparation is in order. If the rest of you have yet things to off load, I'll see you at the trading post. From there we can together seek out lodging, and prepare ourselves further for the journey.... Actually, speaking of lodgings.." He looks Kalannai. "Is there anywhere in town you might recommend?" He asked, and once an answer is given, saw first to hit up the trading post to buy up rations.

(@DM: Not sure what you'd place on hte limits on how much a thing we can get. But, Rhogar would like to see about paying for 20 days worth of rations. All of which he'll be storing inside the bag of holding he made during break.)

"I agree, let's rest and prepare today so that we can start our travel tomorrow at the first light." Krom says to the group "I will go with you at the trading post Rhogar, I too intend to purchase some rations and a few other trinkets."

 Krom will purchase a grappling hook, a climber's kit and rations for 10 days.

Chip would also head to the trading post. while he is there, he would buy a rope, grappling hook, a climber's kit, and 10 days of salted meat rations. 

Kazri will go to the trading post too. She will also purchase 10 days of rations. One never knows. I think the Boots of the Winterlands will really come in hand here.

Rekuberk does the same and buys the rations for himself as well. "Perhaps we should look into some form of transportation. I am sure they have beasts of burden that are bred to deal with the folder temperatures."

"Lad, I too would prefer to use some form of transportation, but Kalannai said that the trail from here to Hundelstone is becoming impassable and that we should travel by foot." says the dwarf to Rekuberk.

Chill is looking for 10 days of rations.

You easily find the trading post and purchase the gear and extra rations that you seek.  Kalannai Grayfu has also directed you to where you can find a place to sleep for the night.  You are surprised to learn that, despite the size of the city, Fireshear has no inns, just a single guest house, wryly called “the Cells” by locals. It is a building of sparse accommodations but it gives you a decent place to rest overnight.  You find dinner at the a tavern called the Singing Manticore.  Engaging a few of the friendlier locals in conversation you learn more of the area that you are headed to. 

Icewind Dale is far to the north, sandwiched between the Sea of Moving Ice, the Reghed Glacier, and the Spine of the World. It's home to a few tribes of tundra barbarians, reindeer, polar bears, wolves, elk, the fierce tundra yeti, and a white dragon or two.

In the west, as the mountains descend to the Sea of Moving Ice, the ridge falls sufficiently to provide a pass. Through this, caravans journey to transport the ivory scrimshaw carvings that make the Dale financially worth inhabiting. A harsh land almost beyond the reach of the warmer and more settled south, the small amount of warmth generated by the Sea of Swords funnels across the lowest part of the mountain wall, keeping the dale marginally hospitable.

Nomadic tribes who hunt reindeer huddle next to the three lakes (Maer Dual-don, Lac Dinneshere, and Redwaters), and the dwarves in their tunnels attempt to survive in the harsh land. Evil creatures flourish in hundreds of mountainous delves, and Icewind Dale has the reputation as a hideout for those seeking to lose themselves.

In this bleak tundra is the farthest bastion of civilization in the Savage Frontier, a loose confederation of 10 towns and villages known collectively as the Ten Towns. The towns are located on or near the three deadly cold lakes, the habitat of the knucklehead trout (found nowhere else in Faerûn). The lakes of Icewind Dale are justly famous for their fishing.

On the way you will pass through Hundelstone.  For most people, Hundeistone is either the last point of civilization before taking the pass north to Icewind Dale or the first welcome sign of refuge after the wearying trip back. For the town’s inhabitants, Hundelstone is a gateway to the riches—and dangers—of the subterranean realm beneath the Spine of the World. Many of the dwarves and gnomes here spend their days excavating tunnels, mining ore, or smelting and smithing the local iron and tin. Meanwhile, the few score human residents are generally sellswords or would-be adventurers who earn a living as caravan guards and beast hunters in the crags. 

The following day, the sky overcast and a light snow falling you head north along the ten-trails.  The snow cover increases as the first day passes but the general direction of the path is easy to follow.  The further north you go, the colder the temperature gets during the day.  At night it is even worse.  Hundelstone is just about 50 miles north along the Ten Trail but trouble begins some ten miles away from Hundelstone, on a gray, overcast afternoon. Chill, who is scouting ahead, identifies that the gray clouds covering the sky promise snow—and likely a storm.  

Snowflakes begin to fall within the hour, and grow thicker and thicker in the next few hours of travel until it’s difficult for characters to see even thirty feet ahead of them through the torrent of snowfall. You need to hurry toward Hundelstone, but the Ten Trail is almost completely invisible beneath the snowfall.

Chill needs to make 5 survival rolls, with advantage as someone can help.

Everyone needs to make 5 CON saving throws.

.

Survival rolls with advantage

28

18

23

29

23

CON saving throws

12

13

16

7

4

Kazri CON Save:

7

24

18

10

19

(Does Boots of the Winterlands helps Kazri at all?)