Cruise Guide: 15 Tips and Things to Do in Skagway, Alaska

It’s hard to imagine a more “Alaskan” port than sailing into Skagway. When you think of the state, you likely imagine small, remote, rustic towns that sit in the middle of soaring mountains.

That’s exactly what you get in Skagway.

Skagway mountains
Sitting at the end of a channel, Skagway has water on one side and mountains everywhere else. It features stunning beauty and plenty to do and see.

It served as a hub during the Klondike Gold Rush, but today has transformed into a major tourist destination that plays up the historic charm for cruise ship passengers. All of it is packed into a valley between soaring mountains that has to be seen to be believed.

If it’s your first time visiting the port of call, then there is plenty that you should know before you arrive to make the most of your time. From what to do in Skagway to tips on getting around, we have everything you want to know for visiting the Alaskan port….

Skagway’s Claim to Fame Was a Jumping Off Point for the Gold Rush

Wondering just exactly what a town is doing in such a remote spot, surrounded by nothing by mountains and water? The answer is gold.

In the late 1800s, gold was discovered in the Yukon — a place that to this day can be difficult to reach. While there were several routes there, sailing to Skagway and then making the trek over the White Pass through the mountains was a popular way.

As prospectors flooded in, the town grew. But then, as the gold rush quickly died down, the population plummeted from thousands to just hundreds. With the rise in popularity of cruises, however, Skagway has started to enjoy a second life.

Skagway Today Is Definitely a Tourist Town

Today, Skagway is a small, rustic town that plays up its turn of the century “golden” past.

If you visit Skagway and find it has a different feel than some of the other ports in Alaska, you aren’t alone. In our opinion, many ports are towns that also cater tourists. Skagway is more of a tourist town.

The entire downtown area revolves around cruise ship tourism. In many ways, that’s a great thing as it’s easy to get around, there’s plenty to do and see, and nearly every storefront caters to tourists, such as souvenir shops, restaurants, and breweries.

On the other hand, if you’re looking for what life is like in current Alaska, it’s not a great example. Even so, the scenery makes the port a great spot to visit.

It’s One of the Most Stunning Ports You’ll See (And You Won’t Believe It Until You See It)

Every port you visit in Alaska will have some dramatic scenery and landscape. But perhaps nowhere is as stunning as Skagway. Honestly, no matter how many pictures or videos you see, it won’t do it justice.

That landscape is due to Skagway’s location. It sits at the end of a narrow channel of water, meaning in one direction is the channel and the entire rest of the spot is surrounded by mountains. Even coming in on a cruise ship — which is normally the largest structure around for miles — you are completely dwarfed by the natural landscape.

Hungry? Try a Klondike Doughboy

The Klondike Doughboy is a dinner-plate-sized fried dessert covered in cinnamon and sugar. Think of it like a funnel cake or huge donut.

What the heck is a Klondike Doughboy? It might be the tastiest thing in Skagway, even if it’s not the best for you.

On 3rd Avenue, there is a storefront called Alaskan Fry Bread which is home to the Klondike Doughboy. The pastry is essentially a dinner-plate-sized piece of sweet dough deep-fried and then sprinkled with cinnamon and sugar. Think of it as a massive donut or funnel cake. It’s served on paper towels (not even a paper plate!), and you simply walk around town chowing down on it.

Truth be told, the Klondike Doughboy is delicious (and only costs $7!), but it’s large enough to feed 2-3 adults. And it’s definitely not something you want to overeat.

There Are 3 Different Cruise Docks, Accommodating 4 Ships

For such a small town, Skagway can handle a significant number of ships. In fact, the three different cruise docks (Ore Dock, Broadway Dock, and Railroad Dock) accommodate four ships, meaning that there can be potentially 10,000 cruise passengers — or more — during a single day.

During our stop, we noticed Disney at the Ore Dock (which is furthest west in the port), Holland America at the middle Broadway Dock, and Princess and Royal Caribbean at the easternmost Railroad dock. The good news is that all the docks have paths leading right into town, with easy walks.

Look at the “Painted Rock” Time Capsule

Skagway painted mural of cruise ships
As a right of passage, cruise ship crews have painted a spot on the rock wall next to the dock. Paintings go back decades.

If you dock on the easternmost docks in Skagway, then you’ll be right next to what amounts to a time capsule done in paint. It’s seemingly become a tradition for a ship to have an area painted on the rocks that rise above the pier when they come to visit.

You’ll see paintings from Carnival, NCL, Holland America and more. We saw some markings going all the way back to 1982 — 40 years ago. Each one marks the occasion when a ship visited the port.

What will really pique your interest is wondering how some of these were painted. They can rise 20 or 30 feet above the water on a steep rock face.

Take a Ride on the White Pass & Yukon Route Rail

White Pass Rail, Skagway
One of the most popular excursions is a ride on the White Pass railway, which takes you from Skagway up into the mountains.

If there is one excursion that’s most popular in Skagway, then it has to be taking a scenic ride on the railway. Skagway was an important jumping off point to head to the Yukon over the White Pass during the Klondike Gold Rush. In just a few years, however, a railway was built to make that trip easier.

Well, today you can now ride the rails on a scenic route that takes about three hours and carries you up into the mountains. You get some of the most postcard-worthy vistas you can imagine as the train heads along the pass.

It is a bit pricey — around $135 per adult — but you can’t do this anywhere else in the world. You can book an excursion through your cruise line or just head to the ticket office when you get off the ship. The station is right by the cruise docks, so you can’t miss it.

Walking to Town? Look for the Shapes to Tell You the Right Way

Skagway is extremely easy to navigate. It’s only about 10 minutes to walk from the ship to town, and it’s laid out largely in a grid. Plus, you can see the ships easily from town as a landmark.

Even so, if you’re worried about finding your way, then there’s a navigation tool to help you. Along the walkways between the ship and town are colored shapes painted on the path. Each dock has a different shape (purple square, orange circle, blue triangle, and red circle). So as you get close to the ships, just look for the shape that corresponds with your pier. Follow it and you’ll easily be able to find your way back.

Don’t Want to Walk? There’s a $3 Shuttle to Town

Heading into town is a bit of a walk — about 10-15 minutes depending on which spot your ship is docked. If you don’t want to walk, then you’re in luck.

In a town the size of Skagway, there isn’t a big transportation network. However, there is a “SMART Bus” (more of a shuttle, really) that picks up and drops off at points around town, including the pier. The cost is $3 for a one-way ride into town or $5 for an all-day pass.

We’d suggest the $5 pass as you’ll see markers all around town where it stops, providing a ride for folks that don’t want to or can’t easily walk.

This May Be the Farthest North You Ever Travel

For many people, visiting Skagway may be a memorable spot because it is the farthest north they will ever venture on the planet. The town sits about 59.5 degrees north — the same latitude as the southernmost point of Greenland, and well north of most of Europe.

And with every step you take into town (and especially if you take a train ride through White Pass), then you are setting a new record for the farthest north you’ve been.

We personally took a walk through the town and before we turned around the head back to the ship, took a picture of the spot realizing that we may never reach a point that far north on the planet again.

Don’t Forget to Mail a Postcard (But It Might Take a While to Arrive)

There is a U.S. post office in Skagway, perfect for mailing a postcard back home.

If you want to write to someone back home, then Skagway offers the perfect opportunity. Stores around the town sell all sorts of postcards along with stamps, with pictures of everything from wildlife to mountains, cruise ships, and more.

After you write your note, then you can drop the cards in the mailbox at the Skagway Post Office. It’s located at the corner of 6th Avenue and Broadway, at the farthest edge of all the historic buildings in the main part of town.

Just know that due to the location, it can take more than a week for your card to arrive, depending on where it is headed.

Interested in Learning About the Gold Rush? Head Here…

The Klondike Gold Rush National Historical Park will teach you everything about the gold rush that led to the boom of Skagway.

As mentioned, Skagway was a starting point for many as they headed to find gold in the Klondike. If you’re interested in this history (which the town revolves around), then head to the Klondike Gold Rush National Historical Park Visitor Center. Operated by the National Park Service, this spot tells the history of the gold rush. There’s a museum with photos and artifacts from the era, along with a video that explains the time in more detail.

It doesn’t take long to go through and it will give you a greater appreciation for what so many people went through in hopes of striking it rich. The center is located at 2nd Avenue and Broadway, right as you enter town.

Head on a Helicopter Tour to Glaciers

Want something that’s uniquely Alaskan? What about taking a helicopter ride to go land on and explore a glacier? We can think of nowhere else that it’s possible but here.

When you arrive to Skagway, you may notice that there are helicopters constantly heading in and out of the area. There’s an airport right near the cruise ports. From there, you can catch a ride on a helicopter that will take you out to nearby glaciers. After the ride over, you’ll actually land and be able to walk on the glacier itself.

Just know that prices are expensive. The two-hour tour runs about $340 per adult for the once-in-a-lifetime experience.

Want a Little Nature in Town? Try the Pullen Creek StreamWalk

The StreamWalk provides a quiet spot next to a small pond and crystal-clear stream to sit and enjoy the beauty of the surrounding area.

Skagway features stunning natural surroundings. No matter which way you turn, there are gorgeous mountains. If you really want to enjoy the beauty without going far, then look for the Pullen Creek StreamWalk.

This small walking trail with park is located between the docks and the town, so you’ll pass by as you leave the ship. It has a small pond and a stream, along with some grassy areas to sit and enjoy.

In other words, if you want a pretty place to relax with a crystal-clear Alaskan stream, this is it.

Visit the Red Onion Saloon for a Bite, Drink, and a Peek at the Naughty Side of Skagway

It’s a little hard to explain exactly what the Red Onion Saloon is, but you likely don’t want to miss it. Set in a historic building by the cruise piers, you’ll no doubt pass it heading into town.

Inside, it plays up Skagway’s past. You can grab a drink or a bite to eat, but 120 years ago it also served as a bordello. Today it features not just food and drink in a lively atmosphere but upstairs is also a brothel museum. Staff also play a part in the history, dressed up as “madams” as they provide tours.

The Red Onion does suggest that “parents and guardians should use their discretion as tour material is a tad risque…”

Map of Skagway, Alaska


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