How to Plan a Cycling Vacation: Tips & Gear for First-Time Bike Trips

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In this episode of Vacation Mavens, we are joined by adventure traveler and blogger Sherry Ott of OttsWorld. We dive into what it takes to plan a successful cycling vacation — everything from choosing destinations and tour types, to picking the right gear, training beforehand, and recovering well. Whether you’re a biking newbie or looking to level up your next bike‐based trip, this one’s packed with insights and practical advice.

Sherry Ott is a long-time travel blogger (since 2006) specializing in adventure travel, especially for women. She started leading small group trips in 2018, including unique “cat lady tours” in Japan. Sherry began serious biking during the pandemic, upgrading to gravel bikes and exploring both domestic (U.S.) and international routes (Chile, France, Prince Edward Island). She is passionate about making bike travel accessible, safe, and fun for all skill levels.

Episode Highlights

Planning & Choosing a Trip

Decide between guided and self-guided tours — guided trips offer support and community, while self-guided give you more flexibility.
Research destinations with strong bike infrastructure (trail networks, signage, support).
Check elevation, distance, and trail type (paved vs. gravel) to match your comfort level.
Look for tour companies that provide e-bike options if you want extra support.
Read reviews, ask about group size, and confirm whether you can bring your own gear (seat, mirror, pedals).

Training & Fitness Prep

Start riding regularly at home to build saddle time and comfort.
Practice on terrain similar to your trip (gravel, hills, road).
Work on balance, confidence, and endurance.
Don’t underestimate elevation — even moderate climbs can feel tough over multiple days.

Safety & Comfort Gear

Always bring your own helmet for the best fit and safety.
Pack a rear-view mirror (handlebar or helmet mount) for traffic awareness.
Wear bright, high-visibility clothing so drivers and riders can see you.
Bring rain gear and layers — weather can shift quickly.
Prioritize comfort over style on the bike.

Recovery & Wellbeing

Use compression socks or leggings (e.g. Vim & Vigor) to reduce muscle fatigue.
Hydrate often and refuel with snacks during rides.
Allow time for rest and stretching after long days.
Be mindful of long flights post-trip — keep circulation flowing with compression wear and movement.

Helpful Resources

Adventure Cycling Association – maps, routes, and trip planning tools.
Tour operators like Experience Plus, Biketours.com, and Backroads.
Tourism boards for bike-friendly regions with trail networks and infrastructure.