Alaska - Haines & Skagway Multisport

Trip Length6 Days
Group Size4-12
Activity level
Starting from
$4,399for REI Members
$4,839 for non-members
DeparturesMay 2025-Aug 2025

Spend 6 days hiking, cycling, and kayaking through the adventure capital of Alaska.

Sitting amid the convergence of towering mountains; massive glaciers; flowing rivers; and the deepest fjord in North America are the southeast Alaska hamlets of Haines and Skagway. As equally impressive as their jaw dropping scenery are the unique cultural, natural, and historic characteristics, which give each town its one-of-a-kind charm.  

The quiet corners of Haines, where coastal rainforests, turquoise blue waters and snowcapped mountains invite intrepid travelers to explore a bounty of world-class outdoor adventure. Skagway, with its bustling charm, storied past, and jaw-dropping scenery. Where gold rush stampeders met the breathtaking yet rugged terrain of the Chilkoot trail. Both towns offer endless opportunity to explore the majestic natural and human history of Southeast Alaska, and we’ll spend 6-days tapping into the best of what these Inside Passage playgrounds have to offer.   

The 48,000-acre Chilkat Bald Eagle Preserve is one of the best locations to watch the majestic raptors along the Inside Passage.

Trip Highlights

  • Spend the day kayaking at the foot of sky-high peaks and hanging glaciers
  • Unplug at our luxury camp sitting along the crystal blue waters of the Chilkat Inlet
  • Cycle along the historic Haines Highway in route to the Jilkaat Kwaan Heritage Center
  • Bike from the gold rush town of Skagway to the ghost town of Dyea
  • Hop aboard the White Pass & Yukon train in route to our hike along the Laughton Glacier trail

Activities

This trip is rated Moderate [3]. Activities include hiking, biking, and kayaking. Participants should be capable of completing a hike of up to 7 miles with elevation gains/losses of up to 921'; cycling up to 44 miles at a time over rolling paved or gravel roads (ebikes available as well as vehicle support); and kayaking in open water for up to 6 hours.

  • Cycling
  • Kayaking
  • Hiking

What's Included

Five nights accommodations; admission to heritage center or museum; all park usage and permit fees; cycling and kayaking gear as noted in gear list; round trip train tickets aboard the White Pass & Yukon Route railway; all gratuities related to services that support the itinerary, other than lead and assistant guide; transfers to/from airport or ferry; all meals as noted in the daily itinerary.

Accommodations

Historic inn, 1 night; Canvas Cabin Tents, 2 nights; hotel, 2 nights.

Your Adventure Itinerary

Itinerary map for Alaska - Haines & Skagway Multisport
Day 1

Meet your guides in Haines before hiking to Battery Point

Welcome to Haines, Alaska! We meet our guides and traveling companions at our hotel this afternoon. After introductions we're off on a scenic hike to Battery Point. Surrounded by vibrant green coastal rainforest, we're quickly enveloped in the quintessential beauty of Alaska's Inside Passage. After popping out of the forest onto a small rocky beach, we are treated to spectacular views of Chilkoot Inlet, where we'll scan the surrounding waters for possible sightings of harbor seal, Stellar sea lion and Humpback whale. Back in Haines we'll enjoy our first dinner together before retiring to one of Haines' most beloved and historic hotels. Dinner included.

Hiking: 4 miles, elevation gain/loss: ~500'

Day 2

Cycle from Haines to Klukwan and visit the Jilkaat Kwaan Heritage Center

Today we bike along the historic Haines Highway. First used as a transport route for indigenous communities, the scenic highway also passes through the 48,000-acre Chilkat Bald Eagle Preserve. We’ll enjoy a picnic lunch outside the Jilkaat Kwaan Heritage Center, located in the Chilkat Tlingit community of Klukwan. We’ll then spend time exploring the center, which is home to a rich array of precious ancestral artifacts. We’ll finish the day with a return ride along the Haines Highway before a hearty dinner at our luxury camp. All meals included. 

Important Note: All guests have the option of selecting an e-bike for today’s ride. Please inform your Customer Service Specialist ahead of time if this is an option you’d like to use.  

Cycling: 44 miles on mostly paved highway with gentle undulations and curves, elevation gain/loss: 1,950’. 

Day 3

Spend the day kayaking through the turquoise blue waters of Chilkoot Inlet or Chilkoot Lake

This morning, we begin a remarkable journey to one of the area's most beautiful kayaking destinations. Before hopping in our kayaks your guides will provide a thorough orientation to our final route, our tandem kayaks, weather, gear, and will also provide a refresher on kayaking strokes, safety, and boat handling. Our final itinerary will be selected based off weather and water conditions. However, both routes offer a spectacular guided opportunity to explore the remarkable waters of southeast Alaska. All meals included. 

Kayaking: 7-10 miles, approximately 6 hours. 

Day 4

Hop the fast ferry from Haines to Skagway before biking to the ghost town of Dyea

Welcome to Skagway! This morning, we depart for the second leg of our journey and the northernmost point of Alaska’s Inside Passage. The hopping town of Skagway has a rich and storied past. As one of Alaska’s key entry points into the heart of the Yukon gold rush, in 1976 the National Park Service designated three areas within and surrounding Skagway as the Klondike Gold Rush National Historic Park – a 4th unit is in Seattle, WA. After arriving in Skagway, we’ll check into our hotel before hopping in the saddle for a ride to Dyea, a ghost town nestled in the Taiya River Valley. Later this evening we’ll have a bit of time to explore Skagway on our own before enjoying dinner at the Skagway Brewing Company. All meals included. 

Cycling: 18 miles; elevation gain/loss: 1,400’ 

Day 5

Ride the White Pass & Yukon Route to the Laughton Glacier Trailhead

This morning, we hop aboard one of the most unique modes of trailhead transportation; the White Pass & Yukon Railway. First opened to passengers in February of 1899, the route over White Pass offers tourists a glimpse into the past and hikers a convenient option into the heart of spectacular backcountry terrain. After a scenic train ride, we’ll disembark at the Laughton Glacier trailhead and begin our journey to the trail’s namesake. Starting in a lush green forest and ending at the expansive foot of a geological masterpiece, we’ll experience a diverse array of southeast Alaska’s quintessential natural beauty. Later this evening we’ll enjoy a celebratory dinner in Skagway before bidding our new friends farewell. All meals included. 

Hiking: 7 miles; elevation gain/loss: +/- 921’  

Day 6

Depart Skagway on your own

Breakfast this morning is provided at our comfortable accommodations in Skagway. The remainder of the day has been reserved for your journey out of Skagway, although transportation out of Skagway will need to be arranged on your own. There are several options available, including both ferries and flights. Recommendations can be found in your Pre-Departure Information for this trip or by speaking with one of our Customer Service Specialists. Breakfast included. 

Itinerary map for Alaska - Haines & Skagway Multisport

Gear List

The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.

Already booked this trip? Sign into your online traveler profile for a more detailed list of what you'll need.

REI members can shop for gently used gear online or at most REI stores. Members can also trade in pre-loved used gear online or at any REI store in exchange for REI gift card credit. Check out Re/Supply at REI to learn more.

We provide

What to pack

Contact Us

Feel free to give us a call at 1 (800) 622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales ( 1 (800) 426-4840 ) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.

Trip specifics may change over time. Reviews reflect the version of the trip that was active at the time the reviewer took it. Please review the itinerary as described above and call our team for any additional details.