Skagway Trail and Sail

If you’re heading to Skagway and looking for a way to see the area beyond the typical cruise ship excursions, the Skagway Trail and Sail tour might just be worth considering. It’s a combination of e-biking through scenic spots and sailing along one of North America’s longest fjords, which means you get a diverse and active day out that’s pretty unique.

What makes this tour stand out? First, the self-guided e-bike ride lets you set your own pace and soak up the views without feeling rushed. Second, sailing on the sailing sloop Hopscotch offers a peaceful, scenic cruise—plus a chance to spot eagles, whales, or seals if luck is on your side.

Of course, this experience isn’t perfect for everyone. It’s geared toward those with moderate physical fitness, since there’s some biking involved, and it’s a small group tour, which means a more personalized vibe. If you’re someone who loves nature, quiet exploration, and a dash of adventure, this could be just the ticket.

Key Points

• Eco-friendly travel combining biking and sailing offers a low-impact way to explore Skagway’s natural beauty.
• The self-guided e-bike ride provides flexibility and scenic stops like waterfalls and historic sites.
• The sailing portion takes you through the Inside Passage, with chances for wildlife sightings.
• The tour is limited to 6 travelers, making for a more intimate experience.
• It’s a full 6-hour excursion, ideal if you want a relaxed but active day.
• The overall ratings are perfect at 5.0 based on three reviews, indicating strong satisfaction.

A Deep Dive into the Tour Itself

This tour kicks off at Klondike Electric Bicycles, a well-reviewed shop that supplies high-quality e-bikes and helpful staff. From the start, it’s clear they aim to make your experience smooth—they give instructions and a map, making the biking part approachable even for those new to e-bikes. The bike ride is self-guided, which means you set the pace, stop where you like, and really take in Skagway at your leisure.

The Stops on the Bike Route

Your first destination is the Gold Rush Cemetery. It’s a poignant spot where you hear stories of Skagway’s rough-and-tumble past, described by one reviewer as “Only a little better than hell on Earth.” It’s a simple 15-minute stop, but it packs a lot of history into that short time. It’s a great way to get context about the town’s colorful past.

Next, you’ll visit Lower Reid Falls, just a quick five-minute walk from the bike route. At 65 feet tall, this waterfall makes for some pretty memorable photos. According to reviews, the ease of the walk and the natural beauty make this a highlight, especially if you love nature.

Then, you’ll cycle along Broadway Street in downtown Skagway, where historic buildings echo the gold rush era. It’s a brief 30-minute look at the town’s past and present. The architecture and stories from guides or signage can really bring the old town to life.

Transition to Sailing

After your cycling adventure, you’ll head to the Small Boat Harbor, where Captain Brendan and the sailing vessel Hopscotch await. This part of the tour is where the magic of the Inside Passage unfolds. Spending about three hours on the water, you’ll explore waterfalls, spot hanging glaciers, and possibly eagle, whale, or seal sightings if the weather cooperates.

The sailing experience is described as peaceful and scenic, with the boat gliding past some of North America’s most impressive fjords. It’s a perfect way to unwind after the biking, with a charcuterie box provided to enjoy during your cruise.

The View from the Skagway Overlook

Before wrapping up, you’ll visit the Skagway Overlook—a quick 15-minute stop offering panoramic views of the town. It’s another photo opportunity and a moment to appreciate the rugged beauty surrounding Skagway.

What to Expect and Practical Info

The entire tour lasts roughly six hours, making it a solid half-day activity that balances physical activity with relaxing sailing. The price of $265 per person reflects the multi-part nature of the experience, including bike rental, guided stops, and the sailing trip—so, it’s a competitive option if you’re after variety and quality.

Because the tour is small—max six travelers—you’re likely to get more personalized attention, which many reviewers appreciated. The group size also helps maintain a flexible, laid-back vibe.

Considerations

The tour requires moderate physical fitness, mainly for the biking portion. While electric bikes make pedaling easier, you should be comfortable riding on somewhat uneven terrain. The sailing is more relaxed, but be prepared for the weather—if it’s rainy or too windy, the sailing might be canceled, but you’d be offered a different date or a refund.

Booking is recommended well in advance—on average, most people reserve about 143 days ahead—showing how popular this experience is among cruise passengers. The cost might seem high, but given it combines two different activities and offers stunning scenery, many find it excellent value.

Authentic Feedback from Travelers

Reviewers praise this tour for its stunning views and knowledgeable guides. One reviewer noted that the e-bikes were very good quality and that staff was helpful and clear with instructions. They mentioned the experience as “a great day,” highlighting how well-organized the tour was.

Another appreciated the chance to avoid crowds and enjoy Skagway’s natural beauty in a more serene setting. They described the activity as perfect for adventurous cruisers seeking quieter, more scenic options.

Even those who couldn’t do the biking still enjoyed the sailing, with one reviewer emphasizing excellent communication and the adventure on the water. It’s clear that even if the biking isn’t available, the sailing alone makes for a memorable outing.

Final Thoughts: Should You Book This Tour?

This Skagway Trail and Sail experience offers an engaging blend of outdoor activity and tranquil sailing, ideal for travelers who enjoy experiencing nature up close without the crowds. The small group size and personalized pace make it particularly appealing for those who want a more intimate look at Skagway’s natural and historic beauty.

If you’re an active traveler comfortable with moderate biking and looking for a scenic, peaceful day on the water, you’ll likely find this tour a real highlight. It’s especially suitable if you appreciate wildlife sightings and stunning fjord views.

However, keep in mind that the activity level is moderate, and weather can impact the sailing, so flexibility is key. It’s worth booking early to secure your spot, especially during peak cruise season.

FAQ

Is this tour suitable for someone who doesn’t bike often?
Yes, the e-bikes are high quality, and staff give clear instructions. Since it’s self-guided, you can ride at your own pace. The bikes make it easier, but some physical effort is still involved.

How long does the biking portion last?
The bike ride itself is flexible, but the stops include a 15-minute visit to the Gold Rush Cemetery, a 5-minute walk to Lower Reid Falls, and a 30-minute ride along Broadway Street. It’s a ride designed to be manageable and scenic.

What can I expect on the sailing trip?
You’ll sail the Inside Passage, exploring waterfalls and viewing glaciers. There’s a chance to see eagles, whales, and seals. It’s peaceful and scenic, perfect for relaxing and taking photos.

How much does the whole experience cost?
The tour is priced at $265 per person. This includes bike rental, the stops, and the sailing trip—offering a multi-layered experience for the price.

What if the weather is bad?
The tour relies on good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.

How many people are in the group?
The maximum group size is six travelers, ensuring a more personal and less crowded experience.

Where does the tour start and end?
It begins at Klondike Electric Bicycles on 5th Avenue and ends at the Skagway Small Boat Harbor, with easy access back to port or town.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund. Less notice means no refund, so plan accordingly.

If you’re craving a day that combines active exploration with the tranquil beauty of Skagway’s fjords, this Trail and Sail experience might just be your perfect match. It’s a balanced day of history, nature, and peaceful sailing—all in one package.