Skagway is a fantastic place for boat tours and cruises, thanks to its unique location on Alaska’s Inside Passage. Unlike many ports, Skagway offers a blend of historic charm and pristine natural beauty, making it ideal for those who want to combine sightseeing with active experiences.
We’re especially fond of Skagway Trail and Sail, which perfectly balances eco-friendly exploration and scenic sailing, all wrapped into a six-hour adventure.
It’s a great way to experience the area’s waterfalls, historic sites, and the breathtaking upper Inside Passage — a highlight in itself.
While Skagway offers a variety of boat experiences, the best ones tend to emphasize small-group sailing, local history, and environmental consciousness. Whether you’re a nature lover or a history buff, these tours promise memorable moments on the water. Below, we’ve rounded up the top two boat tours in Skagway, each with its own unique appeal and standout features.
1. Skagway Trail and Sail
At number one is the Skagway Trail and Sail, an eco-friendly tour that offers a mix of self-guided biking and sailing. The day begins at Klondike Electric Bicycles, where you’ll hop on a self-guided electric bike to explore some of Skagway’s most iconic spots.
You’ll visit the Gold Rush Cemetery, providing a vivid glimpse into the town’s rough-and-tumble days. The Lower Reid Falls is a short walk from the bike route, offering stunning photos of a 65-foot waterfall.
The biking tour also includes a ride along Broadway Street in historic downtown Skagway, where you can admire the well-preserved Gold Rush-era buildings. Afterward, you’ll meet Captain Brendan at the Small Boat Harbor to board the 50-foot sailing sloop Hopscotch for a three-hour sail through the Inside Passage.
This sail explores waterfalls along Taiya Inlet, providing a chance to see Alaska’s coast from a different perspective. The tour concludes with a bird’s-eye view of Skagway from the overlook, making this a well-rounded experience.
What makes this tour stand out is its commitment to sustainability and personalized exploration. The self-guided bike segment allows you to explore at your own pace, and the combined land-and-sea adventure offers a thorough taste of Skagway’s natural and historic highlights.
Rave reviews mention the “excellent combination of activity and relaxation,” and the $265 price is quite reasonable considering the full day of varied experiences.
Bottom Line: This tour is perfect for active travelers who appreciate a mix of biking, history, and sailing, all with an eco-conscious approach.
2. Skagway: Trail and Sail
Ranking second is the Skagway: Trail and Sail, which provides a similar combination of electric biking and sailing for about $278 per person. It’s slightly more expensive but offers a comprehensive experience that’s ideal for those wanting a full day of active exploration and scenic cruising.
This tour starts with electric bikes to visit key points of interest in Skagway, including the Gold Rush Cemetery and picturesque viewpoints. The highlight is sailing along North America’s longest fjord, which offers spectacular views of glaciers, waterfalls, and wildlife.
The trip emphasizes eco-friendly practices and small-group intimacy, making it a favorite among travelers seeking a more personal experience.
The review for this tour is highly positive, with a perfect 5/5 rating. Participants mention the “beautiful scenery” and “fun, easy biking,” making this a top choice for families and outdoor enthusiasts. The exclusive sailing along the fjord offers a chance to see parts of Alaska rarely experienced on larger cruise ships.
Bottom Line: If you want a more comprehensive, scenic cruise paired with active exploration, this tour provides excellent value and a memorable adventure.
How to Choose
When deciding between these two beautiful boat tours, consider your interests and fitness level. The Skagway Trail and Sail is best for those who want a mixture of self-guided activity and sailing, plus a focus on local history. Meanwhile, the Skagway: Trail and Sail leans more toward scenic cruising and wildlife viewing along the fjord, perfect for nature lovers.
Both tours are ideal for active travelers comfortable with biking and sailing, but if your priority is exploring Alaska’s coast and glaciers from a small boat, the second option offers a slightly more focused cruising experience. Booking early is recommended, especially in summer months, as these tours tend to fill up quickly.
Final Thoughts
Skagway’s boat tours and cruises offer a fantastic way to enjoy Alaska’s stunning coastline, historic sites, and wildlife. For a balanced day of biking, history, and sailing, Skagway Trail and Sail is a top pick. If you prefer a scenic fjord cruise with a focus on wildlife and natural beauty, the Skagway: Trail and Sail is a perfect choice.
Both tours deliver memorable experiences for different interests—whether active exploration or scenic cruising—and are well worth booking in advance. Whichever you choose, you’ll leave with a deeper appreciation for Skagway’s natural wonders and historic charm.