Jay H said:
There is a funny guy who runs the van service there that will drop you off at the trailhead for Dyea, his card is plastered everywhere downtown. Check out the Red Onion saloon (former Brothel) to eat.
That would be the world famous Dyea Dave! The guy is classic... Has some cheesy jokes, but again, a local that knows everything and anything... I had him hold some of our gear while we hiked the Chilkoot... When I saw him after I got back to town and out of the clinic, he remembered me right away and got our stuff to me ASAP... There are other people that drive folks out to Dyea, the Chilkoot Trail trailhead, but this guy is the ONLY one to take... You will find him at the ferry terminal, he is always there when a boat arrives... Look for the guy that can be Yukon Cornelius' brother... That's Dave. His sister runs the hostel in town.
I would recommend the White House B&B for a place to stay... A bit pricy, but well worth it for the breakfast in the am, great baked goods!
The Red Onion was ok to eat at, but do it after the cruise ships leave, the place is on the tourist trail and gets BUSY! After 5pm though, the place is empty except the locals... A great place to get coffee is the Haven Cafe, which is a few blocks of the main drag. They also have great sandwiches and baked goods at reasonable prices compared to the prices on the main drag in town. It is also just up from the public library where you can get free internet, just sign up for a block of time, they were open 7 days a week this past summer.
Also Moe's Frontier Tavern on the main drag is the locals place to hang...
Overall Skagway is a small town... It takes a whole 10 minutes to walk across town, at a stroll, and maybe 15-20 minutes to walk in the other direction. You should read the police blotter that they post on their newspaper's website... They had a case a few months back of loud music... The officer saw someone sleeping who would not wake up to answer the door, so they went in, turned the music off and left their card there in case the sleeping person awoke and wondered what happened... Classic! I joke that I was waiting for the moose to stroll across the town ala Nothern Exposure.
Whatever you do, if you ever end up in Skagway, look for the locals places, I learned this out when I was killing time. A slice of pizza near at a tourist place was $3!!!! A whole pizza was $20... Over at the towny sports bar it was a buck a slice for some great pizza...
In Juneau, you have to stop by the Alaskan Brewery which is out in the Mendenhall Valley... FREE samples... I made sure I stay well hydrated there one afternoon after my experience in Skagway...