Skagway: Chilkoot Trail Hike & River Float with Pickup

Summary

Chilkoot’s wild path and Dyea’s quiet waters in one day

You’ll set out from Skagway with a small group, hiking the first stretch of the historic Chilkoot Trail with a local guide who knows every twist in its story. After catching your breath in Dyea valley, you’ll float quietly downriver — no crowds, just forest and water sounds. Port pickup and snacks are included so you can focus on what’s around you instead of logistics.

What’s the experience like?

“You brought bear spray, right?” Our guide grinned as we tumbled out of the van at the Chilkoot Trailhead outside Skagway. I could smell wet spruce and something sharp — maybe moss? The air felt different here, kind of heavier but clean. We started walking, boots crunching on old roots. There were stories everywhere: gold rushers, Tlingit traders — our guide (I think her name was Jamie?) pointed out a rusted horseshoe half-buried in mud. She said thousands of people tried their luck on this same path. I tried to imagine that many feet on these narrow switchbacks. Couldn’t.

The hike was tougher than I’d guessed — not impossible, just enough to feel my legs by the time we stopped for snacks near a bend in the trail. Someone spotted an eagle overhead and everyone went quiet for a second. The river below sounded like static on an old radio. My hands were cold but it felt good, you know? Jamie told us about how Dyea used to be a boomtown — now it’s just forest and silence except for the river and sometimes laughter when someone slips (me). No crowds here at all.

I didn’t expect to love the float part so much. We climbed into the raft (I nearly lost my footing but played it cool) and drifted along Dyea valley, watching green blur past. There was this moment where the sun came out for like two minutes and everything turned gold-ish — I still think about that view sometimes when I’m stuck in traffic back home. Jamie steered us around a logjam and told us to look for seals or otters; we didn’t see any but somehow that made it better? It felt private. The whole thing lasted maybe 40 minutes but time got weird out there.

Step-by-step itinerary

Day 1 — Chilkoot Trail hike and river float

• Travel 9 miles to Chilkoot Trail
• Hike first 2 miles of Chilkoot Trail
• Float down Dyea valley river
• Return 9 miles to Skagway

Top questions

How long is the Chilkoot Trail hike on this tour?

You’ll hike about 2 miles along the Chilkoot Trail before reaching the river float section.

Is transportation from Skagway included?

Yes, round-trip transport from Skagway port to the trailhead is included.

How strenuous is this tour?

The hike is moderately strenuous; good physical condition and sturdy shoes are recommended.

How long does the river float last?

The float portion down Dyea valley lasts approximately 40 minutes.

Are snacks provided during the tour?

Yes, snacks are included during your hiking break.

Is this tour suitable for young children?

The minimum age is 5 years old; all participants should be able to handle moderate hiking.

What should I wear or bring?

Dress for changing weather and wear sturdy walking shoes with good traction; rain gear is smart too.

How many people are on each raft?

The maximum per raft or group is 11 people.

What’s included

Your day includes port pickup and drop-off from Skagway, guided hiking along two miles of the Chilkoot Trail, snacks during your break in Dyea valley, and a peaceful river float with all gear provided before heading back to town together.