Skagway Transportation

Skagway Jobs In Guest Services & Transportation

This small Alaskan port town, situated at the north end of Lynn Canal, has a population of 700 year-round and 1,400 summer residents. Skagway is a popular destination with over 750,000 visitors a year, who come for the history that dates back to 1898 and the Klondike Gold rush. There were over 500,000 people who passed through the town in search of gold. The town still retains much of that turn-of-the-century charm. For the adventurous, the Chilkoot Trail awaits. This trail led prospectors up and over the mountains through some of the roughest terrain known to man. The historic trail still displays relics left behind from those prospectors over 100 years ago.
For more information on the Skagway area, we recommend visiting these sites: and


Skagway, Alaska is surrounded by mountains that will enhance your enjoyment on your days off with camping, hiking, rock climbing, river floats, train rides, and numerous other attractions. Become a part of a family that works at having a good time and giving great service to people on vacation.

Housing Options

Housing options include dormitory and hotel-style living which typically includes shared rooms with bathrooms down the hall. All employee housing areas are smoke free environments. Some off-property housing is available in the small community, but is very limited. Cost of employee housing is $8.00 per day which is deducted from your paycheck. Amenities at employee housing include:
Laundry facilities
Television is available with other amenities in the common room for entertainment

Why Work in Skagway?

Skagway is full of small-town charm and brimming with plenty of outdoor adventures all within walking distance. Also, upon successful completion of the terms of the employment agreement, an attractive discounted travel program may be available including cruises with Princess Cruises & Holland America Line.
The Skagway Day Off Guide has more great recreation ideas!


You may fly directly into Skagway, Alaska, on a company provided flight or you may choose to purchase your own transportation and receive a $550.00 reimbursement upon completion of your seasonal work agreement. You will be met by one of the employees of the company to escort you to the Main Office to get you signed in for training and housing. They will take you to your place of residence. Due to the nature of the employment agreement this does not apply to employees who are hired under the J1 visa program.

  • Location: Skagway, Alaska – The Garden City of Alaska
  • Number of Employees:  100
  • Housing Type: Dormitory and Hotel
  • Typical Season: May 1 through September 28
  • Types of Jobs
    • CDL Driver-Guides
    • Tour Desk  Representatives
    • Office/Dock Representatives
    • Luggage Crew
    • Detail Crew