The experience of cruising with Disney Cruise Line to Alaska is just incredible, and if you haven’t experienced it, you may want to add it to your bucket list.

The first Port of call on our Alaska cruise itinerary was the tiny town of Skagway. The town might be tiny in size, but it is huge on preservation. Skagway offers visitors an authentic glimpse into the gold rush era, and the city looks as though it hasn’t changed a bit from all those years ago. There is actually a rule in Skagway that if any new construction is built, it has to be themed as it was in the 1920s, so the town keeps its authentic look. This is one of the few towns that did not burn to the ground back in the day, as it’s pretty sheltered by giant mountains.


When trying to figure out which port excursion to go on in Skagway, my first choice was the White Pass Scenic Railway. I read the description of the excursion and loved the idea of riding a vintage rail car and going on a narrated trip aboard the train. Then I read more about the train ride, and it stated that the train climbs almost 3,000 feet over 20 miles of steep grades and cliff-hanging turns. Umm…NOPE. I’m not into either of those, thank you very much.

I looked at Skagway‘s Original Street Car City Tour, and that was definitely more my style, so I booked that one. Guests board an old-time sightseeing bus right from the cruise ship’s pier and learn about the historic events and the history of Skagway. I love the idea of not only seeing the town but also learning about its history.

One of my favorite things was that our conductor was wearing a costume from the 1920s, and she was adorable! She even had on Minnie Mouse ears with pink flowers from Epcot International Flower and Garden Festival since she was picking everyone up from the Disney Wonder. I thought that was such a cute touch, and they matched her vintage dress perfectly.

We boarded the 1927 yellow street car right by our ship, and we were off. The front of the vehicle reminded me of my dad‘s Model A Ford that he worked on all throughout my childhood in our garage. It was the cutest thing. Our tour wasn’t too crowded, and there were plenty of seats for everyone on the street car.

The bus took us through the town of Skagway, which only has four streets; we actually drove on all four of them! The residential area in Skagway was just as quaint as you may have guessed. The houses were mostly pretty small, craftsman style, and cute as can be. The flower gardens around the houses were beautiful. There was even a funky tree in someone’s yard that had blue glass bottles all over it.

We also learned the story of Skagway’s hero and villain, which was honestly quite entertaining. I am not going to go into all of the details of the story here as it was a big part of the tour, and I don’t want to spoil it for anyone who might go in the future. I will say that it was an interesting story that took us to a small graveyard on the outskirts of town. One tidbit that I found fascinating about this cemetery was that some graves had what appears to be a Victorian bedframe surrounding them – they call it a “surround” – and it’s meant to make the dead feel like they’re resting in bed. This means that the families of the buried loved ones had money in which to spend on such frivolous things.

We visited a lookout spot up on the side of a mountain that gave us a great view of our ship from afar. We were also able to look across and see some of the landslides that have occurred in Skagway. It’s crazy to think of how gigantic the landslides were, but we were glad to learn that no one was injured in them.

Would you believe that there is no doctor or hospital in Skagway? Like, at all. So, if you are someone who lives in Skagway and needs to go to an emergency room for a broken bone or another medical emergency that cannot be handled by a medical assistant, you’ll have to be taken to the nearest hospital in Juneau via helicopter to the tune of $30K. Woah!

Not only is there no hospital, but most folks who live in Skagway travel to Canada to do their grocery shopping as there is only one small grocery store in Skagway. Apparently, fresh produce can be a hot commodity, and items like an avocado can cost you around $6 each. I should note that bringing produce back into Skagway from Canada is not allowed, so they have to deal with whatever they can get at their one small grocery store. With all that being said about food shopping, there are two breweries and five churches in the tiny town, surprisingly.

Our conducter told us that only around 700 people live in Skagway year-round and that most folks come into town just for the cruise season and then go back to their hometowns. I can only imagine how tough the COVID closures must have been on the folks who live and work there. I heard some other numbers thrown around on tours others in our group were on, but I’m sure they’re all approximates.

Overall, I’m really glad that I had the opportunity to visit Skagway and I recommend spending a bit of time in town. We could have been dropped off for shopping in town after the tour was over, but elected to go back to the ship as we had other videos to film.

Have you been to Skagway? I’d love to hear about your experience in the comments below!

About Post Author