Sherri Kyle

Hi, I’m Sherri. For over a decade, I’ve worked in the adventure travel industry as a guide, trip researcher, and logistics planner. I’ve led and designed trips across Japan, Austria, Czech Republic, Canada, Mexico, and the U.S., with a special love for bikepacking and hiking. Whether it’s helping first-time adventurers or seasoned athletes, I love sharing insights to make outdoor experiences smoother and more rewarding.

Country Expertise

Japan: Kyushu; Hokkaido; Nagano Region Czech Republic: Southern Bohemia; Prague Austria: Wachau Valley; Northern Austria; Vienna Canada: Whole Country Mexico: Whole Country United States: Whole Country
Bikepacking: Mexico; Japan; Czech Republic; Austria; Canada; United States Hiking: Japan; Czech Republic; Austria; Canada; United States Skiing: Japan; Austria; Canada; United States
Kyushu: Whole Area Hokkaido: Whole Area Nagano Region: Whole Area Southern Bohemia: Whole Area Prague: Whole Area Wachau Valley: Whole Area Northern Austria: Whole Area Vienna: Whole Area Canada: Whole Country Mexico: Whole Country

The outdoors has been both my escape and my career. It’s where I challenge myself, find clarity, and explore new places—whether on foot, on skis, or on my bike.  But in my own time, I’ve also mapped out and completed multi-day to year-long bikepacking trips, always looking for the next challenge.

Where I Can Help

📍 Japan – I know the island of Kyushu’s hiking trails inside and out, and I can help you plan ski adventures in Hokkaido and Nagano.

📍 Czech Republic – From the trails of Southern Bohemia to the historic streets of Prague, I can offer insider tips on active adventures in the region.

📍 Austria – I’ve spent time in the Wachau Valley and Northern Austria, exploring everything from wine country to biking the legendary Danube bike path.

📍 Canada & the U.S. – Whether it’s hiking, biking, or skiing, I’ve got experience guiding and designing adventures in both countries.

📍 Mexico – My latest bikepacking trip took me through remote parts of Mexico, testing my limits and connecting with incredible locals.

My Favorite Adventure

One of my most rewarding adventures was bikepacking through remote regions of Mexico. The landscapes were rugged, the terrain was challenging, and the people I met along the way made it unforgettable. There’s something about pushing yourself through the unknown that makes every mile worth it.

Specializations & Interests

🚵 Bikepacking Logistics – I’ve planned and executed everything from short multi-day rides to year-long expeditions.

❄️ Ski Touring & Alpine Adventures – Particularly in Japan and Austria, where I’ve spent time exploring major ski regions.

🗺️ First-Time Adventurers – I love helping people ease into adventure travel, whether it’s their first hike, their first bike tour, or their first trip abroad.

What you get:

  • 25-min Zoom call with your expert
  • Personalized TripGuide with your recommendations, logistics info, and a day by day approach following the call
  • Custom Google map, curated by your expert

Note: your map and TripGuide are shareable so you can give to your travel companions

Send me a message

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Common Questions

How does Outdoorable work?
Outdoorable connects you with experienced outdoor pros through 1:1 video calls. Whether you’re deciding between destinations, need insider tips for a specific trail, or want advice tailored to your skill level, our experts are here to help. Simply browse expert profiles, book a call, and get the guidance you need to plan your next adventure with confidence.
What can I ask an Outdoorable expert?
Anything about your outdoor trip! Need advice on hiking routes, family-friendly trails, or navigating backcountry terrain? Want to know the best time to visit Patagonia or if a specific climb is doable for your skill level? Our experts are here to give personalized insights based on their firsthand experience.
How long are the calls?
Calls are 30 minutes, giving you plenty of time to ask questions, explore options, and get personalized advice. If you need more time, you can always book a follow-up session.
Can I choose which expert to talk to?
Yes! You can browse detailed expert profiles to find someone who matches your destination or activity needs. Whether it’s a hut-to-hut trek in the Alps or beginner-friendly kayaking in Croatia, you’ll find an expert who’s been there and done that.
What happens after I book a call?
Once you book a call, you’ll get a confirmation email with a link to share your questions or trip details in advance. This helps the expert prepare and ensures you get the most out of your session. You’ll also receive a link for the video call closer to the appointment.
How much does it cost?
A 30-minute call costs $60, with $45 going directly to the expert. We believe in fair pay for our pros who have invaluable expertise while keeping it affordable for adventurers.
What if I need to reschedule or cancel?
We get it—plans change. You can reschedule or cancel your call up to 24 hours before the scheduled time. Just head to your confirmation email for details on how to make changes.
What if I don’t find the call helpful?
We strive to connect you with the best experts and provide actionable advice. If you feel your call didn’t meet your expectations, let us know. We’ll work with you to make it right. All Pros can see your questions in advance, and they will let us know beforehand if they don’t think they are the best person to provide insight.
Can I share the call with someone else?
Yes! Whether you’re planning a trip with friends or family, feel free to include them in the call. Just make sure everyone’s ready to hop on when the session starts.
Do experts plan my trip for me or give me an itinerary?
No, Outdoorable is not a trip-planning service. Our experts provide personalized advice, answer questions, and guide you with insights to help you plan your trip. Think of it as having a knowledgeable friend with all the lowdown so you can plan your perfect trip.
How do you choose your experts?
Our experts are handpicked for their firsthand experience, regional knowledge, and ability to give actionable advice. Many are professional guides, trip designers, or seasoned adventurers with years of expertise. That means their jobs are to find the best places off the beaten path. Needless to say… you’re in good hands.
What kind of trips can Outdoorable help with?
Outdoorable is perfect for all types of nature-based adventures:
• Planning a big bucket-list adventure
• Deciding between destinations based on your outdoor skill level and interests
• Finding hidden trails, parks, routes
• Preparing for a solo trip, family outing, or group adventure