Skagway Walking Tour With Madam Shirley Wood .

A madam named Shirley Wood, gold‑rush tales, creaking brothel floorboards, and a few beers to finish the day, my memorable and very human visit to Skagway.

The ship docked in Skagway mid‑morning, and I woke up with my leg feeling very sore. I honestly considered skipping my tour, but I reminded myself that I might never return to Skagway, so I pushed through. Before doing anything else, I went for another acupuncture session. Needles, electrotherapy, the works, back, legs, shoulders, knees, even my skull. It helped enough that, after breakfast, I felt ready to face the day.

Skagway Walking Tour.

When I stepped off the ship, I was greeted by a woman dressed as a Madam from the Red Onion Saloon and Brothel. Her stage name was Shirley Wood, a clever choice. While waiting for the rest of the group, I chatted with her. She was originally from New York, trained as an actress, and her parents were from Brighton in Hampshire, not far from where I used to live in Fareham. She was lovely to talk to, but once the group arrived, she slipped back into character as Madam Shirley Wood.

We boarded a small bus for the short ride into town. From there, she led us on foot around Skagway, sharing stories about the buildings, the people, and the rough, often tragic history of the gold rush. It was only a couple of hours long, but it was one of the most interesting walking tours I’ve ever taken.

Our final stop was the Red Onion Saloon. Because we were on the tour, we were taken upstairs into the old brothel. The rooms were tiny, the beds even smaller, and much of the original building remained untouched, old wallpaper, gaps in the walls where the wind still slipped through. It felt like stepping straight into the past.

After the tour, we went downstairs into the saloon itself. I didn’t stay for food or drink, but I did buy a T‑shirt before slowly making my way back to the ship.

Return to the NCL Spirit.

That evening I chose the buffet instead of a restaurant, easier on my legs, and later sat in the Local Bar chatting with a man from Hawaii. He introduced me to his wife, who then invited me to join her and her friends on another cruise later in the year. It was a kind offer, but I had no idea where I’d be by then, so I had to decline.

After several beers, I headed back to my cabin to sleep at around 22:00. I didn’t last long. I lay down, closed my eyes, and the next thing I knew it was early morning and we were approaching Skagway’s neighbour on the itinerary. I’d slept straight through the night.

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