Alaska Adventure {Skagway Dining & Excursions}

Skagway was our last port of call on the ship. The town is located at the northernmost point of the Inside Passage and was at the heart of the gold rush. The town has been restored to its gold rush era look, with wooden boardwalks and unique buildings.

Visiting Vancouver & A 49th State Alaska Adventure

Arriving in Skagway

We were in port today from 7AM to 9PM, which was ample time to do and see it all! The town itself is quite small and very easy to explore. It is a little bit of a walk from the port to the historic district, but there is the option of a paid shuttle. We all walked as it was flat and easy.

Klondike Doughboy & Glacial Coffehouse

Our first order of business was breakfast! We couldn’t decide between two places so we did both since they were located just steps away from each other.

Klondike Doughboy was my favorite sweet treat (posing as breakfast) from any place we visited in Alaska! They claim to sell the “best fry bread in Southeast Alaska” and I feel like that must be true. :-) The portion size is huge so we split one between the four of us. The glutton in me wishes we’d done two.

Right next door is Glacial Coffeehouse. We had an assortment of bagel sandwiches that we shared, as well as coffee and smoothies and all were good! (no pics for some odd reason!)

Chilkoot Trail Hike and Float Tour

Our main event for the day was the Chilkoot Trail Hike and Float Tour. The Chilkoot Trail was something we heard about multiple times when researching and then once we arrived in Alaska. The Chilkoot Trail was originally a trade route for Native and First Nations people, but during the Klondike Gold Rush in 1897-1898, it was the highway that thousands of men, women and children completed in their journey from Dyea, Alaska to Lake Bennett, BC.

Our guide picked us up right in the little historic district for a short, scenic van ride. Along the way, he shared the history of Skagway and areas we passed, as well as neat insight on what it is like to be a seasonal resident and life so far away from a city. We made one stop at this beautiful overlook.

We started with the 2-mile hike through temperate rain forest and along the river. It was absolutely beautiful and serene, but parts were very rocky, steep and difficult to navigate. I would not recommend this activity for everyone! Our guide shared fascinating information both about the vegetation as well as life during the Gold Rush on the trail. The kids loved stopping to try watermelon berries along the way!

The reward at the end of the hike is a gorgeous downstream float through the Klondike Gold Rush National Historical Park! Wellies are provided.

After a quick riverside snack, we loaded up in the van and were headed back to town. We loved this excursion and getting out in the middle of beautiful Alaska!

Read more about Skagway Shore Excursion: Chilkoot Trail Hike and Float Tour 2019 –

I should note that only my family of four did this excursion. Sister’s family went to a summer musher camp in this Yukon Dog Sledding activity. She reported back that they thoroughly enjoyed it! She said she’d pick the glacier dog sledding first, but that this was a great alternative if that one didn’t work for your family.

My parents did the Skagway Streetcar Tour, which they highly recommend for a less adventurous day than hiking. They said it was extremely entertaining and enjoyable.

The White Pass Railway is the most popular excursion in Skagway, but since we already had a couple of train rides as part of our adventure we chose these instead.

Skagway Brewing Company

At the recommendation of our tour guide, we were dropped off at Skagway Brewing Company for lunch. It was absolutely delicious and we welcomed a hearty meal after our morning adventure. I highly recommend anything halibut in Alaska, and the fish sandwich here was quite tasty. One other note on Alaska, all of the local beers are fantastic! I’m not a regular beer drinker, but I had more than my fair share here and don’t regret a thing. :-)

The Days of ’98 Show

From our walk through town first thing in the morning, I got a bee in my bonnet that I wanted to see The Days of ’98 Show. Honey and the boys were not interested, so I procured my ticket for one for the 2:30 PM show and settled in to my front row seat!

In its 96th season, The Days of ’98 Show continues to bedazzle audiences with the tale of Soapy Smith, Alaska’s most notorious outlaw. Soapy reigned over Skagway during the wildest days of the Klondike Gold Rush, and this colorful vaudevillian musical recounts his incredible story. The show features can-can dancers, ragtime music, riotous humor, and the great con-man himself, Soapy Smith!

I thoroughly enjoyed myself and was so glad that I went. I absolutely recommend attending if you find yourself with a free afternoon in Skagway. I do think my boys would have enjoyed it, but they were all quite happy roaming around Yukatania Point.

After the show I was inspired to hunt down Jeff Smith’s Parlor, just a few blocks away.

We all met back on the ship with time for a quick soak in the hot tub before dinner. Tomorrow brings another favorite day: Glacier Bay!

As a Virtuoso affiliated travel adviser, I have global connections with the best hotels, cruise lines, airlines and tour companies, and I secure exclusive amenities for my luxury clients.  I have recently refocused my travel business primarily on Disney destinations, but am always happy to book and consult on destinations I have personally visited, as well as other Virtuoso resorts and all major cruise lines. Contact me to learn more and start designing your dream vacation today!

[email protected]
Learn More About My Services
Consultation Request

Dixie Delights
join me as I travel, decorate, create & celebrate
Instagram | Pinterest

Dixie Travels
perfectly planned trips & our travel adventures
Book Now | Learn More
Instagram | Facebook | Pinterest


One thought on “Alaska Adventure {Skagway Dining & Excursions}

Leave a Reply

Your email address will not be published. Required fields are marked *