Skagway Trail and Sail

Imagine combining the thrill of exploring Skagway’s historic streets on a quiet, electric bicycle with the serenity of sailing through North America’s deepest fjord. This tour, offered by Klondike Electric Bicycles for $265 per person, lasts about six hours and is designed for those eager to see the region’s highlights without the crowds. Starting with a self-guided e-bike ride, you’ll visit iconic sites like the Gold Rush Cemetery, Reid Falls, and the Skagway overlook, before ending with a scenic three-hour sail aboard the Hopscotch.

What we love about this experience is how it blends active exploration with relaxing sea vistas. The e-bike provides a smooth, eco-friendly way to cover more ground comfortably, especially with well-maintained bikes and helpful instructions. Plus, sailing past waterfalls and glaciers in the Inside Passage offers a rare chance to see marine wildlife, with eagle sightings and whale spouts likely to make your day even more memorable.

A possible consideration is the physical aspect—while the tour is suitable for those with moderate fitness, some stops involve walking, and the overall activity level might be a stretch for less active travelers. Also, availability of bikes can vary, so booking well in advance helps ensure the full experience.

This tour suits adventurous travelers who appreciate a mix of history, nature, and authentic Alaska scenery. It’s ideal if you want to avoid cruise ship crowds and explore at your own pace, enjoying both land and sea highlights with a knowledgeable guide and crew.

Key Points

• Eco-friendly Exploration: Ride a quality e-bike to see Skagway’s top sites comfortably and quietly.
• Rich Historic Context: Visit the Gold Rush Cemetery and learn about Skagway’s colorful past.
• Spectacular Views: Enjoy bird’s-eye vistas from the Skagway overlook and waterfalls along the route.
• Scenic Sailing: Experience the Inside Passage’s waterfalls, glaciers, and potentially marine wildlife during a three-hour sail.
• Authentic Experience: This tour offers a genuine, crowd-free way to appreciate Alaska’s natural beauty.
• Limited Group Size: With a maximum of six travelers, it’s an intimate way to see the area.

Starting Point: Klondike Electric Bicycles in Downtown Skagway

Your adventure kicks off at Klondike Electric Bicycles on 5th Avenue. The shop’s reputation for quality e-bikes and helpful staff is well earned—reviewers praise how easy it is to get set up and how clear the instructions are. We found that their bikes are in excellent condition, making the ride smooth and effortless, especially for those unfamiliar with electric bikes.

The shop is conveniently located near public transportation and within walking distance of the cruise docks, making logistics straightforward for cruise passengers. Since the tour is limited to six participants, booking in advance (average booking time is about 143 days) is highly recommended. This small group size ensures personalized attention and a more relaxed experience.

The E-Bike Ride: Exploring Skagway’s Historic and Natural Sites

This self-guided ride is one of the highlights. It allows you to set your own pace, giving ample time to stop and enjoy each location. The route includes:

Gold Rush Cemetery

A visit here offers a glimpse into Skagway’s tumultuous past. The cemetery tells stories of those who shaped the town during the Gold Rush era—some heroes, some villains—and their often dramatic ends. With only 15 minutes allocated, it’s a quick stop but packed with history. Visitors often comment that learning about Skagway’s early days deepens the entire experience, making the scenic tour more meaningful.

Lower Reid Falls

A short walk from the bike route takes you to Lower Reid Falls, a 65-foot waterfall named after a local hero. The combination of a brief walk and stunning cascade makes it a favorite photo spot. One reviewer called it “sure to make for some amazing photos,” which is exactly what you’ll want to capture.

Downtown Skagway and Broadway Street

Riding along Broadway provides a taste of Gold Rush-era architecture. The historic buildings and lively streets tell stories of a town that boomed and faded in the span of a few years. Many travelers appreciate this part for its authenticity and the chance to imagine the bustling rush that once filled these streets.

Skagway Overlook

The ride culminates at the Skagway overlook, giving you a bird’s-eye view of the town and surrounding mountains. It’s a perfect spot for photos and for soaking in the landscape. The 15-minute stop allows for a quick rest and some reflection on the scenic beauty around you.

Transition to the Sailing Adventure

After completing your bike tour, you’ll head to the Skagway Small Boat Harbor at 205 Congress Way. Here, Captain Brendan and crew await aboard the sailing sloop Hopscotch. The boat’s reputation for smooth sailing and friendly crew makes for a relaxing transition from land to sea.

The Inside Passage Sail

This three-hour voyage is the real showstopper. You’ll sail through Alaska’s famous Inside Passage, the longest and deepest fjord in North America. The boat glides past waterfalls cascading from hanging glaciers, and if luck’s on your side, you might spot eagles soaring overhead, whales breaching, or seals lounging on ice floes.

The sailing experience is nothing short of spectacular. The crew, including guides like Brandon and Sierra as mentioned in reviews, are knowledgeable and eager to share insights about the landscape and wildlife. The boat itself provides a cozy, intimate setting, ideal for relaxing and taking photos.

A charcuterie box is waiting for you to enjoy during the sail, adding a touch of luxury to the adventure. Whether you’re a nature lover, a birdwatcher, or simply seeking tranquil vistas, this part of the tour delivers.

The Final Stop: Return to Town and Practicalities

The tour concludes at the harbor, with easy access back to the cruise ships or town. The harbor’s proximity to the town center and shuttle services make logistics straightforward. This seamless transition means you can extend your time exploring or head back for the next port of call without hassle.

Value and Considerations

While $265 per person might seem steep, it reflects the quality of the experience—small group size, high-quality equipment, and professional crew—plus the unique combination of land and sea exploration in a stunning setting. The reviews underscore the “great outdoors experience” and the knowledgeable guides, both of which add severe value.

One thing to keep in mind is the physical requirement—moderate fitness is advised, as you’ll be biking and walking. Also, availability of bikes can be limited, so early booking is advisable. Weather can influence the sailing, but the company offers rescheduling or refunds if conditions are poor.

Who Will Love This Tour?

This experience is perfect for travelers seeking adventure without overexertion, those interested in history and natural scenery, and anyone who wants a personalized, crowd-free cruise experience. It’s especially suited for those who enjoy combining active exploration with relaxing, scenic sailing.

FAQs

Is this tour suitable for all fitness levels?
Yes, as long as you have moderate physical fitness, since it involves some biking and walking. The bikes are electric, making the ride easier.

How long does the entire tour last?
Approximately six hours, including the bike ride, sightseeing stops, and the three-hour sailing.

Can I book just the sailing or the biking?
This tour offers both activities as a package. If the biking isn’t available on your date, you might still be able to enjoy the sailing portion by contacting the provider directly.

Do I need to bring my own equipment?
No, the bikes are provided, and the sailing includes all necessary gear. Just bring your sense of adventure and appropriate clothing.

What’s included in the price?
The cost covers the e-bike rental, sightseeing stops, the sailing trip, and the charcuterie box.

What if the weather is bad?
The company offers full refunds or rescheduling if poor weather cancels the sailing or biking.

Is there a limit on group size?
Yes, a maximum of six travelers ensure a more personalized experience.

Where do I meet for the tour?
At Klondike Electric Bicycles on 5th Avenue for the start, and at the Small Boat Harbor for the sailing.

How far in advance should I book?
Booking about 143 days in advance is typical, so plan early for the best chance to secure your preferred date.

The Skagway Trail and Sail tour offers a beautifully balanced day of land and sea adventures, perfect for those who want to see more than just the usual cruise port hustle. The combination of self-guided e-biking through historic streets and scenic sailing past glaciers and waterfalls makes it a rich experience packed with authentic Alaska sights. The small-group format, knowledgeable guides, and stunning vistas provide excellent value.

If you’re the kind of traveler who enjoys active, immersive experiences that steer clear of crowds, this tour is an excellent choice. It’s especially well suited for those who appreciate history, wildlife, and breathtaking scenery all wrapped into one memorable day.

Note: Always check weather conditions and book in advance to ensure availability. Consider your physical comfort with biking and walking, and prepare for a day of genuine exploration and relaxation in one of Alaska’s most scenic regions.