🎥 Watch Episode 5 first: 

*By Billy Bohan Chinique, Vice President, Marketing & Digital Innovation

Watch it first, then read this — mostly because I want you to see my face during the helicopter landing before I try to describe it in words.

I joked on set that this episode should just be called “planes, trains, helicopters, and boats,” and honestly, by the time we wrapped filming, that joke had basically become the real title in my head. Skagway hands you one of the longest port days on the whole itinerary — roughly 7am to almost 9pm — and we used every single hour of it.

Michelle Bentubo, Chief Operations Officer at Virgin Voyages, has done Skagway more than ten times and told me this is consistently one of the ports where first-timers hit information overload the fastest, because there’s genuinely so much packed into one day. Noted. Confirmed. That was me.

More Modes of Travel in One Day Than the Rest of the Trip Combined

That length matters for how you should think about planning your own Skagway day, so let me flag it up front: this is not a port where you casually wander for a couple of hours and call it done. It rewards — honestly, it requires — a genuinely full day.

What You’ll See in This Episode

We started in the sky, lifting off from the TEMSCO helipad on Skagway’s waterfront for a scenic flight over the surrounding fjords before landing directly on Meade Glacier — solid ice, near sea level, close enough to actually walk on.

Back on the ground, we moved into the Exclusive White Pass Railway & Red Onion Saloon bundle: a fully narrated ride in vintage rail cars climbing the historic White Pass, a route originally cut through the mountains some 125 years ago using nothing but hand tools and dynamite, over a construction period of just 27 months.

The day got considerably more bawdy and human once we reached the Red Onion Saloon & Brothel Museum, where a costumed guide known as “Madam Purity” walked us through the story of a boomtown that saw roughly 100,000 stampeders pass through during the gold rush era. We closed on a more reflective note, weighing the actual human and environmental cost of that gold rush against the romanticized version most people, myself included before this trip, carry around in their heads.

Behind the Scenes: Building a Railway with Dynamite and Nothing Else

The detail from this episode that stuck with me most: learning exactly how the White Pass & Yukon Route railway got built in the first place. This isn’t a route carved out with modern machinery over a comfortable, multi-year timeline. Workers cut this line through genuinely brutal mountain terrain in just 27 months, roughly 125 years ago, using hand tools and dynamite as their entire technology stack.

Riding the finished product today — smooth, narrated, comfortable in vintage cars — makes it almost impossible to viscerally connect with what that construction actually involved. I tried to bridge that gap by letting our onboard guide, Jacqui from White Pass, walk through the specifics on camera: the route runs from Mile 0 to the Summit across fourteen cars, and crucially, doesn’t require a passport on its own, despite technically brushing the US-Canada border area.

My pro-tip from filming, which I’ll pass along here: keep a camera pointed both in front of and behind the train at different points during the ride. Some of the most dramatic mountain drops and waterfall views are only visible looking backward as the train climbs, and it’s genuinely easy to miss them if you’re only shooting forward.

A Closer Look at Jacqui's Narration

One detail I didn’t want to lose in the edit is just how much Jacqui's narration shapes the whole experience of the rail journey. It’d be easy to assume a scenic train ride mostly sells itself on the views alone. It doesn’t. The difference between watching mountains pass in silence and having someone walk you through exactly what you’re looking at — which switchback needed the most dynamite, where workers were housed during construction, how the route got surveyed before any modern engineering conveniences existed — completely changes the register of the whole thing. Actually engage with the narration instead of treating it as background noise while you photograph the scenery. A fair amount of what makes the 27-month construction story land emotionally comes directly from that narration, not just the views.

The Real Story: What the Gold Rush Actually Cost

I didn’t want this episode to be pure spectacle — helicopters, trains, a saucy brothel museum — without acknowledging the more complicated history underneath it. The gold rush that built Skagway brought roughly 100,000 stampeders through a town that had essentially no infrastructure to support that population before the rush began. That’s a staggering number of people moving through a remote frontier settlement in a very short window, and the human cost of that — on the land itself, and on the people who lived through the boom-and-bust cycle that followed — is a genuine story, not just a footnote.

The Red Onion Saloon segment captures part of that human story directly. The museum preserves the building as an actual restored 1898 brothel, and Madam Purity’s tour doesn’t sanitize the history — she walks guests through the saloon’s working-brothel history directly and matter-of-factly, without playing it for cheap laughs or glossing over it. It’s a strange, specific kind of authenticity: a champagne toast and a historical tour of a working brothel, delivered with genuine warmth and humor instead of either prudishness or exploitation.

Shore Things Featured

Glacier Helicopter Landing

Lift off from Skagway’s waterfront and fly over serrated peaks, waterfalls, and hanging valleys before landing directly on a glacier for a guided walk on the ice. I landed on Meade Glacier, though the pilot picks the day’s best landing site among Meade, Ferebee, or Chilkat depending on conditions. Guides cover crevasses, melt streams, and glacial geology on the ground, with time for photos and a taste of fresh glacier water, before the scenic flight back to town.

Good to know: the excursion runs about 2 hours total — roughly 40 minutes flying, 40 minutes on the glacier — in a small group of up to six. It’s not wheelchair accessible, and Sailors need to climb in and out with limited assistance. Glacier overboots are provided, so wear closed-toe shoes; no bags, selfie sticks, drones, or liquids permitted onboard (lockers available at the base). Weather-dependent, and a $150 surcharge applies for Sailors 250 lb / 113 kg and over.

White Pass Railway & Red Onion Saloon

A single Exclusive-tier bundle pairing Skagway’s two signature experiences. Ride the narrow-gauge White Pass Railway into the mountains — regularly ranked among North America’s most scenic train rides — past glaciers and waterfalls. Back in town, costumed madams welcome Sailors into the Red Onion Saloon for a champagne toast and a guided tour of the restored 1898 brothel museum, with Madam Purity narrating boomtown history including the roughly 100,000 stampeders who passed through, the “ten dolls” behind the bar, and the ten rooms upstairs.

Good to know: this bundle runs about 4.5 hours total — roughly 2 hours by rail, 1.25 hours by motorcoach, 30 minutes at the Red Onion — and includes a champagne toast (additional drinks available for purchase). Accessible for collapsible wheelchairs if Sailors can manage a few steps, though note 25 steps lead up into the historic brothel building specifically. No passport needed — this bundle stays on the US side of the border.

What This Episode Taught Me About Pacing a Long Day

Filming a day this packed forced me to rethink pacing more than any other episode in this series. With four distinct modes of travel and a nearly fourteen-hour window ashore, there’s a real risk of the whole day feeling like a rushed checklist instead of a coherent experience — exactly the trap I spent all of Episode 1 arguing against.

I addressed that by leaning into the transitions themselves as part of the story instead of just cutting between activities. The walk from the helipad back into town, the wait before boarding the train, the short motorcoach ride to the Red Onion — I kept more of that connective tissue in the final edit than I normally would, because it’s genuinely part of what a day like this actually feels like. If you’re planning your own Skagway day: don’t treat the gaps between activities as dead time to rush through. They’re part of the experience.

Rookie vs. Ten-Timer: Skagway Edition

Michelle told me something on this leg of the trip that stuck with me: after ten-plus visits, she’s stopped trying to do everything Skagway offers in a single day, and instead picks one or two things to go deep on each time. I, obviously, being a first-timer with something to prove, tried to do all four modes of travel in one shot. I don’t regret it, but I fully understand her more measured approach now — by 8pm I was running on pure adrenaline and gift-shop coffee, and she was, predictably, completely fine.

Practical Tips for Skagway

• Decide your excursion combination before you arrive, not on the day. Both featured excursions are substantial commitments, and together with transit and meals, that’s most of a 7am-to-9pm day.
• Weigh the surcharge for the helicopter if it applies to you. Better to know in advance than at check-in.
• Leave the passport worry behind for this one — neither the helicopter nor the railway-and-saloon bundle crosses into Canada.
• If you can only choose one excursion, think about which kind of experience you want more. The helicopter is awe and physical scale. The railway-and-saloon bundle is history and narrative. Neither is the lesser choice.

Pro Tips From Me

• Visit both sides of the car during the ride — the best views alternate depending on which side of the mountain you’re passing.
• Don’t skip the narration on the train even if you’re tempted to just stare out the window.
• Pace yourself — this day is genuinely long, and there’s no shame in doing two excursions instead of all four modes of travel like I did.
• Actually talk to locals if you have downtime — some of my favorite unscripted moments came from conversations that weren’t part of any excursion at all.

Catch you on the flip. 🚁🚂

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