Skagway: Trail and Sail

If you’re seeking a day in Skagway that combines active exploration with breathtaking scenery, the Skagway: Trail and Sail tour offers just that. Designed for those who want to see more than just the typical cruise ship stops, this experience takes you on a self-guided e-bike journey through historic towns and then out on a sailing adventure along the majestic Lynn Canal. It’s a carefully curated blend of history, nature, and gentle adventure that promises memorable views and genuine local insights.

What we love about this tour is how it balances independent exploration with expert-guided sailing. The e-bike portion lets you set your own pace while visiting the famous Gold Rush Cemetery and scenic overlooks, creating a personal connection to Skagway’s past and landscape. Then, the sailing with Captain Brendan offers a peaceful yet awe-inspiring perspective of North America’s longest fjord, where waterfalls, glaciers, and possibly even whales and eagles become part of your backdrop. One potential consideration is that this experience is weather dependent—if the skies turn stormy, the sailing segment might be canceled, but the tour offers full refunds in such cases. This tour is ideal for active travelers and those craving an authentic, scenic day outside the usual tourist routes.

Key Points

• Active and Relaxing Mix: Combines self-guided e-biking with a tranquil sailing experience.
• Breathtaking Views: Pass waterfalls, glaciers, and stunning fjord landscapes.
• Expert Guides: Knowledgeable crew, especially Captain Brendan, enhances the sailing part.
• Flexibility: Self-guided bike tour allows you to explore at your own pace.
• Limited Group Size: Small groups (up to 6) mean a more personalized experience.
• Weather Dependent: Sailing may be canceled in bad weather, but full refunds are available.

You can check availability for your dates here:

A Detailed Look at the Skagway: Trail and Sail Experience

Starting Point: Klondike Electric Bicycles

Your day begins at Klondike Electric Bicycles, a friendly spot that sets the tone for a relaxed, well-organized adventure. Here, you’re fitted with a bike helmet and lock, ensuring safety and peace of mind as you set out on your three-hour, self-guided e-bike tour. The fact that the bikes are electric means even less experienced riders or those with limited stamina can comfortably explore Skagway and Dyea, the nearby gold rush ghost town.

The E-Bike Tour: Exploring Skagway and Dyea

The route takes you through historic Skagway, with stops at key points of interest like the Gold Rush Cemetery, where you can get a tangible sense of the town’s gold rush past. The overlooks along the way are worth pausing at, offering panoramic views of the surrounding mountains and waterways. One reviewer praised the “awesome route along the river,” which suggests the terrain is both scenic and manageable.

You’ll love the independent pace—you decide how long to linger at each stop, making this a flexible, personalized journey. The inclusion of a boxed picnic lunch makes the experience more convenient, allowing you to enjoy a bite while taking in the sights. The cycling component is suitable for anyone over 14 who can ride a bike, ensuring a comfortable ride for most.

The Transition: From Bike to Boat

After your e-bike adventure, you’ll conclude at the Skagway Small Boat Harbor, where Captain Brendan awaits aboard the sailing sloop Hopscotch. This transition from land to sea is smooth, and the short walk or shuttle ride between the bike drop-off and the harbor keeps things simple and stress-free.

More Great Tours Nearby

The Sailing: Exploring North America’s Longest Fjord

Once onboard, the adventure shifts to the water. The sailing in the Lynn Canal promises an unforgettable experience—this is North America’s longest and deepest fjord, renowned for its dramatic waterfalls, hanging glaciers, and unspoiled wilderness. Captain Brendan’s expertise is a highlight for many; as one guest puts it, “We loved sailing with Brendan and Lynn in the bay,” noting the guides’ kindness and knowledge.

Expect to see wildlife such as eagles, whales, and seals—if luck is on your side—and enjoy the peaceful serenity of the fjord’s natural beauty. The 2.5-hour trip offers just enough time to soak in the scenery without feeling rushed, and the picnic charcuterie lunch makes it perfect for a relaxed, scenic meal.

Overall Value and Experience

At $278 per person, this tour offers a well-rounded, premium experience. The combination of land and sea—each with its own charm—delivers diverse vistas and authentic encounters. The small group size ensures a more intimate outing, with the opportunity for personalized attention from guides and crew.

What the Reviews Say

The only review available gives a perfect score, with Kristi from the U.S. calling it “so fun and amazingly kind guides,” emphasizing the genuine warmth of the hosts. The combination of stunning views and knowledgeable guides seems to resonate strongly with participants, making it clear why this tour garners such high praise.

Practical Tips for Participants

• Dress appropriately for both biking and sailing—layers work well, and closed-toe shoes are mandatory.
• Since weather can affect sailing, it’s wise to have flexible plans or be ready for possible rescheduling.
• The minimum age is 14, so it’s not suitable for children under that age or those unable to ride a bike comfortably.
• Small group limits (up to 6) mean booking in advance is recommended, especially in peak seasons.

Final Thoughts: Who Will Love This Tour?

This Skagway: Trail and Sail experience is best suited for travelers who appreciate active pursuits combined with scenic relaxation. It’s perfect if you want a personalized, small-group adventure that takes you beyond the typical tourist spots and into the heart of the Alaskan wilderness. Families with older children, active couples, or solo travelers looking for a meaningful day will find this tour both engaging and rewarding.

If you’re the type who loves stunning landscapes, authentic local guides, and a chance to see wildlife in their natural habitat, then this tour is a smart choice. The blend of history, nature, and gentle adventure makes it a memorable way to experience Skagway in a truly unique manner.

FAQ

How long is the entire tour?
The tour lasts about 6 hours, with 3 hours on e-bikes and 2.5 hours sailing, plus time for transfers and breaks.

What’s included in the price?
You get 3 hours on electric bikes, a helmet and lock, 2.5 hours of sailing, and a picnic charcuterie lunch.

Can I cancel the tour if the weather is bad?
Yes, the tour is weather dependent, and a full refund is provided if sailing is canceled due to weather conditions.

Is the tour suitable for children?
The minimum age is 14, and participants must be able to ride a bike. It’s not suitable for children under 14 or those with certain mobility restrictions.

What should I wear?
Dress in layers, wear closed-toe shoes, and prepare for potential wind or rain while sailing.

How big are the groups?
Groups are limited to 6 participants, ensuring a more personalized experience.

Do I need to book in advance?
Yes, given the small group size and popularity, booking ahead is recommended. You can reserve now and pay later if you prefer flexibility.

This tour offers a thoughtful combination of activity, scenery, and local expertise—perfect for travelers wanting a memorable, authentic Alaskan day. Whether you’re a nature lover, history buff, or just in search of a different kind of sightseeing, Skagway’s Trail and Sail has something to delight everyone.

You can check availability for your dates here: