Skagway sits at the gateway of Alaska’s Inside Passage, and its waters and trails are a playground for cruise passengers craving more than just port shopping. It’s a town famous for its Gold Rush history, rugged scenery, and access to wilderness adventures. Whether you want to glide through fjords on a sleek sailing sloop or go deep into the wilderness on a jet-boat, Skagway offers memorable ways to experience its stunning landscapes.
In this guide, we’ll explore two standout tours—Skagway Trail and Sail and Chilkat River Jet-Boat Adventure—each providing distinct perspectives on the area’s natural beauty and history. We’ll break down what makes each one special, their key highlights, and who they suit best. If you’re pondering how to make the most of your time in Skagway’s waters, this will help you choose the right fit.
Quick Overview
This guide features two top boat-based experiences. The first is an eco-friendly, self-guided e-bike tour ending on a sailing sloop for a relaxing sail with local snacks. The second is a wilderness jet-boat adventure into remote parts of the Chilkat Bald Eagle Preserve, perfect for animal lovers and those craving a rugged, active journey. Both tours run about 6 hours, but they differ dramatically in style and focus.
1. Skagway Trail and Sail
This eco-friendly tour offers a chance to explore Skagway’s scenery both on two wheels and on the water. Starting at Klondike Electric Bicycles, you’ll join a self-guided ride to visit some of Skagway’s most photogenic spots, including a waterfall, scenic vistas, the Gold Rush Cemetery, and Nakhu Bay. The electric bikes make this a relaxed ride, suitable even for those with minimal cycling experience.
After the riding portion, you’ll meet Captain Brendan at the Small Boat Harbor and hop aboard the 50-foot sailing sloop Hopscotch. This part of the tour really shines because it combines active exploration with a peaceful sail. While onboard, a charcuterie box awaits, making it perfect for those who enjoy a gourmet snack amid stunning surroundings. The sail offers excellent views of the mountains and coastline, with plenty of opportunities for photography or just relaxing.
This tour is notable for its environmental focus—they use electric bikes and promote eco-conscious tourism. It’s a great pick for travelers wanting a blend of adventure and tranquility without the crowds. The $265 per person price reflects the quality of the experience, including the self-guided biking, sailing, and food.
Bottom Line: This tour is ideal if you like a balanced day of light activity, scenic beauty, and a laid-back sailing experience. It’s excellent for those interested in local history, nature, and enjoying a quiet moment on the water.
2. Chilkat River Jet-Boat Adventure from Skagway
For those looking to dive into the wilderness, the Chilkat River Jet-Boat Adventure offers a rugged, immersive experience. Starting with a 30-minute scenic bus ride along the Haines Scenic Byway into the Chilkat Bald Eagle Preserve, this trip is as much about the journey as the destination. Your narrator shares stories about the valley’s history, giving context to the stunning scenery.
Once on the river, the specially designed jet boat takes you through a maze of channels, covering 20 miles into the remote wilderness. The vessel’s design allows it to navigate silt-laden rivers, giving access to areas where most boats can’t go. The main highlight is bald eagles, which you can observe in their natural habitat, along with the chance to see moose and other wildlife. The trip emphasizes wildlife viewing and untouched scenery, making it a favorite for nature buffs and photo enthusiasts.
This tour is priced at $348.44 per person, reflecting its unique access to a pristine environment. It’s suitable for travelers who enjoy adventure, don’t mind a little bumpy ride, and want a genuine wilderness experience. It’s worth noting that the trip is longer and more physically active than a typical boat tour, with some bouncing over waves and navigating narrow channels.
Bottom Line: Perfect for wildlife lovers and adventure seekers, this jet-boat ride into the Chilkat Bald Eagle Preserve delivers an authentic Alaskan wilderness experience. It’s best suited for those comfortable with a more active, sometimes splashing, journey.
How to Choose
When deciding between these two, consider your interests and physical comfort. If you prefer a relaxed day with some exercise, combined with sailing and scenic views, the Skagway Trail and Sail is your best bet. It’s excellent for history buffs, food lovers, and travelers who want a gentle introduction to Skagway’s waterways.
On the other hand, if you’re craving wildlife encounters, adventure, and don’t mind a rougher ride, the Chilkat River Jet-Boat Adventure offers a more dramatic, immersive wilderness experience. It’s ideal for active travelers or those eager for a true Alaskan expedition.
Booking early is advised, especially during peak cruise season, as these tours tend to fill quickly. Both tours provide a chance to see Skagway from different angles—one from the calm, scenic side, the other from the wild, untamed backcountry.
Final Thoughts
Skagway’s boat tours each offer a distinct way to experience its natural beauty. The Skagway Trail and Sail blends history, scenery, and relaxation, making it perfect for those who want a peaceful yet engaging experience. Meanwhile, the Chilkat River Jet-Boat Adventure provides a full-on wilderness immersion that thrill-seekers and wildlife enthusiasts will love.
If your time is limited or you prefer a gentle exploration, the sail and bike tour will deliver a memorable, balanced experience. But if you have a passion for wildlife and don’t mind a bumpy ride, the jet-boat adventure is well worth the splashes and bumps. Either way, booking ahead guarantees you a spot for these unique Skagway experiences—each promising a different, authentic taste of Alaska’s wild coast.