Skagway: Stepping Back in Time to the Gold Rush Days

Hey there, adventurer! Grab your imaginary suspenders and your most durable hiking boots, because today we are traveling back in time. Not with a fancy machine, but by pulling into one of the most charming, history-soaked ports in all of Alaska: Skagway.

If you’ve been following along with our “Join Me in Alaska!” May 2027 campaign, you know that I am absolutely bursting with excitement for this 15-day escorted journey. We’ve talked about the calving glaciers and the sleepy charm of Ketchikan, but Skagway? Skagway is where the legends live. It’s the kind of place where you can almost hear the clinking of gold pans and the rowdy laughter from the saloons of 1898.

As a mom and someone who treats every traveler like family, I can tell you that Skagway is usually the port where everyone’s eyes go wide. It’s not just a stop; it’s an experience that stays in your heart forever. Together, we’re going to walk the same wooden boardwalks that the stampeders did over a century ago, and believe me, the magic is still very much alive!

Where Skagway Fits in Our Official Short Version Itinerary

One of the things I love most about this adventure is how beautifully the land tour and cruise portion come together. Our official Short Version itinerary begins with Day 1: Transfer to Florida Airport, flight to Fairbanks. Then we settle into Days 1-3 in Fairbanks with Pikes Waterfront Lodge, the Riverboat Discovery, a Fairbanks City Tour with North Pole, and the breathtaking Wilderness Express Domed Rail to Denali.

Next, Days 4-5 in Denali include Denali Park Village, the Denali Park Tundra Wildlife Tour, Denali Jeep Adventure, the Denali Cabin Nite Dinner and Show, and the Wilderness Express to Anchorage. On Day 6 in Anchorage, we overnight at Marriott Fairfield Inn & Suites and experience the Alaska Wildlife Conservation Center, Turnagain Pass, and the Kenai Mountains. Then on Days 7-8 in Seward, we stay at Harbor 360 Hotel and enjoy the unforgettable Kenai Fjords National Park Glacier and Wildlife Tour.

From there, the cruise portion begins on Days 8-15 aboard the Celebrity Solstice. This is where Skagway shines as one of the signature ports of call alongside Hubbard Glacier, Juneau, Icy Strait Point, Ketchikan, and the Inside Passage. When we arrive here during the cruise, Skagway gives us that wonderful step-back-in-time experience right in the middle of an already breathtaking sailing. It is such a special part of the voyage because it blends rich Gold Rush history, mountain scenery, and that classic Alaska small-town charm into one memorable stop.

Broadway, the main street, is lined with colorful, false-front buildings that look exactly like they did during the height of the gold rush. We’ll spend our time strolling down those famous wooden sidewalks, soaking up the atmosphere, and enjoying one of the most story-filled ports on the entire cruise. And after all these unforgettable moments, our journey wraps up with Day 15: Flight to Florida, Transfer back to Highlands County.

I love seeing the look on my guests' faces when they realize Skagway is not just another port stop, but a meaningful highlight of the Days 8-15 cruise portion of our Alaska journey. Some places are beautiful, some are historic, and some just stay with you. Skagway does all three! If you're wondering how Skagway compares to other stops, check out our post on land tours vs. glacier cruises to see how this fits into the bigger picture of your adventure.

All Aboard: The White Pass & Yukon Route Railroad

Now, if there is one "must-do" in Skagway, it’s the White Pass & Yukon Route Railroad. Honestly, calling it a "train ride" feels like an understatement. It’s a journey into the clouds!

This narrow-gauge railroad was built in 1898 during the Klondike Gold Rush and is considered an International Historic Civil Engineering Landmark: right up there with the Eiffel Tower and the Statue of Liberty! We’ll board vintage railcars and climb nearly 3,000 feet in just 20 miles.

As we wind along the steep cliffs, you’ll see cascading waterfalls, massive glaciers, and the remnants of the original "Trail of '98" etched into the mountainside. I always tell my group to keep their cameras ready, but also to remember to just breathe. The air up there is so crisp and clean, it feels like a gift from above.

It’s one of those "pinch-me" moments where you realize just how vast and majestic God’s creation really is. Witnessing those peaks together is exactly why I started Gina’s Adventures: to share these breathtaking sights with friends like you.

Ghosts, Legends, and the Red Onion Saloon

You can't talk about Skagway without mentioning its "wild" side. After our train ride, we usually head over to the Red Onion Saloon. Back in the day, it was the town's premier brothel and dance hall. Today, it’s a museum and a lively restaurant where the staff dresses in period costumes.

It’s witty, it’s a little cheeky, and it’s a whole lot of fun. If you’re feeling brave, you can take a "Quickie Tour" of the upstairs museum to see how the "soiled doves" of the 1890s lived. It’s a fascinating look at the social history of the era.

And don’t forget to keep an eye out for Soapy Smith! He was the legendary con artist who basically ran the town until he met his end in a famous shootout. You can even visit his grave at the Gold Rush Cemetery just a short trip from downtown. It’s these stories: the triumphs and the scandals: that make Skagway feel so alive.

Nature's Majesty: Beyond the Boardwalk

While the history is incredible, we can’t forget that we are in the heart of the Alaskan wilderness. For those of you who want to stretch your legs and get a little closer to nature, Skagway has some of the most vibrant hiking trails in the state.

Lower Reid Falls is a personal favorite of mine. It’s a relatively easy walk from the Gold Rush Cemetery, and the reward is a stunning, rushing waterfall that feels tucked away from the rest of the world. It’s a great spot for a moment of reflection or a group photo to add to our adventure gallery.

For the more adventurous souls, there’s the Chilkoot Trail: or at least a small portion of it! This was the grueling path the stampeders had to hike to get to the Yukon. Today, it’s a world-famous hiking destination. Even just seeing the start of it gives you a profound respect for the people who came here over a century ago.

Why This Trip is Different

You might be thinking, "Gina, I can book a cruise to Alaska anytime." And you’re right, you can! But this May 2027 Escorted Tour isn't just about the destination; it’s about the togetherness.

When you travel with us, you’re not just a number on a cabin door. You’re part of a community. This trip is personally hosted and escorted by Gina and Travis Rogers, so you’ll have both of us right there with you, making sure every detail is handled every step of the way. We’re also grateful to partner with Jerry at Cruise and Tour Supermarket to help bring this unforgettable adventure together. We take care of the logistics so you can focus on the memories.

Whether we are sharing a laugh over a salmon bake at Liarsville or quietly watching the sunset over the Lynn Canal, these are the moments that build a legacy of cherished experiences. I’ve seen friendships form on these trips that last a lifetime, and that is truly the greatest blessing of my job.

Join the Adventure!

Skagway is a place where history isn't just in books; it’s under your feet and in the very air you breathe. It’s a town that invites you to be a part of its story, and I would be absolutely honored to have you join ours.

Our "Join Me in Alaska!" 15-day journey is filling up, and I don’t want you to miss out on the chance to see the "Galloping Glacier" at Hubbard, the historic streets of Skagway, and the wild beauty of Denali all in one spectacular trip.

Are you ready to step back in time with me?

Click here to see the full itinerary and secure your spot!

Let’s make 2027 the year you finally take that dream trip. I’ve got you covered, and I can't wait to see you on the deck, coffee in hand, as we sail into the heart of the Last Frontier. Together, let's discover the wonders that wait in Skagway and beyond!

Blessings and happy travels,

Gina and Travis Rogers ✝️