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Konnichiwa Reader,

I’ve officially settled into life in Japan for a while—leading tours, scouting new adventures, and basically eating and 'cocktailing' my way through the country (all in the name of research, of course). My Michinoku Coastal Trail hiking tour just wrapped up, and it was everything I love about travel rolled into one trip: an amazing group, bluebird skies, jaw-dropping coastal views, and endless local food, cocktails, and culture.

Next up? My Cat Tour of Japan! (Yes, that’s really a thing—and yes, it’s as adorable and quirky as it sounds.) You can follow along with all the furry encounters on my social channels.

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After the cat chaos, I’m trading paws for pedals and diving into Japan’s growing cycling scene. The country is investing heavily in cycling tourism, and I’m testing a few routes—one along the Michinoku Coastal Trail and another across the Shimanami Kaido, a stunning 70km ride that hops six islands via a string of soaring bridges.

How to Choose the Right Bike Tour For You

If you’ve ever dreamed of doing a bike tour but weren’t sure where to start, you’ll want to check out my recent Vacation Mavens Podcast interview where I share what I’ve learned as a newbie cyclist—plus my best tips on how to choose the right bike tour for you.

• Guided vs. Self-Guided: Guided tours offer built-in support, social connection, and local insight. Self-guided tours are great if you like flexibility and a little independence.
• Research destinations with solid bike infrastructure. Check local tourism board websites to see what trail networks and routes they recommend—and which companies operate there.
• Match your comfort level. Review elevation, distance, and terrain type (paved vs. gravel) before you commit.
• Consider e-bikes! They open up a lot of possibilities—especially if you’re new to cycling or tackling hilly terrain.

What you should look for when looking at bike tour companies:

• Check the bikes. What kind of fleet do they have? Are e-bikes available? How new are the bikes, and what brands do they use? Don't be afraid to call them and talk to them about their bikes.
• Find out their focus. Is the company all about the cycling—or more about the destination? Choose the one that matches your travel style.
• Ask about flexibility. Can you bring your own seat, pedals, or bike computer? Can you switch to an e-bike mid-trip? And will they install them?
• Understand the terrain and traffic. Is it mostly backroads, gravel, or highways with shoulders? How much traffic can you expect?
• Evaluate their pre-trip support. Do they offer training tips, group calls, or pre-departure resources?
• Check group size and guide setup. How many people per tour? Are guides cycling alongside you or driving support vehicles? Can you ride at your own pace or must you stick with the group?

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Good companies and resources I recommend:

For bike travel in the US: Adventure Cycling Association is a fantastic resource for routes, maps, and bike-friendly trail systems across the U.S.

For bike travel in Europe: Experience Plus Cycling tours. Operating for over 50 years and perfect for all levels. I love that you can ride at your own pace instead of staying in a group.

Specifically for Ireland, I like Ireland Walk Hike Bike offers wonderful self-guided options in Ireland. Ottsworld readers get a discount below!

Check out my upcoming cycling tours and join me on one of these trips!

• Portugal Cycling - Join me on a Portugal Camino Cycling Tour with Experience Plus Cycling. Dates: June 2 - 13, 2026 (8 day option also possible) Cost: $6650 - get $300 off with code 'Sherry2026'
  ​Read about my Southern France biking trip with them last spring.
• Patagonia Ebiking - Pedal through the raw, untamed beauty of Patagonia on my ​Patagonia eBike Small Group Tour​—an epic 7-day journey from Puerto Natales to Torres del Paine that blends gravel-road cycling, estancia stays, local cuisine, and wild landscapes. Dates: November 1 - 7, 2026 - 8 spots only! Cost: $5400 ($1350 deposit)​
• Coming soon - Ride Capitol to Capitol with me! Maine/New Hampshire/Vermont cycling trip Autumn 2026

A final thought - one thing I’ve learned over years of travel is that curiosity and movement go hand in hand. Whether I’m hiking a rugged coast, pedaling across a suspension bridge, or chasing cats through Japan’s backstreets, I’m reminded that exploration doesn’t have to be epic—it just has to be intentional.

So here’s to staying curious, moving forward, and finding joy in the unexpected paths.

Happy Travels!

Travel News

Since I'm all about traveling off the beaten track - this article caught my eye - Is it Time to Ditch the Bucket List? There's nothing wrong with having one, but increasingly, they're starting to look remarkably similar.

Combining overnight accommodation and transport in one, night trains are the smart, scenic, and fun way to travel around Europe. Europe’s Most Exciting New Sleeper Train Routes

Ottsworld Tours

Ireland Hiking Tour Through Donegal​
Dates: May 16 - 26, 2026 - only a few spots left!
Cost: 3800€ (aprox. $4434 USD) ( 400€ Deposit)

If you’ve been dreaming of stepping off the beaten path and into landscapes that feel untamed and alive, my Donegal Ireland Hiking Tour will light that fire in you. Think towering sea cliffs taller than the Cliffs of Moher, remote islands, abandoned villages whispering of history, and ridge walks where you can feel the wind roll off the Atlantic. You’ll hike through wild terrain, meet local farmers and tweed weavers, and end each day sleeping in cozy guesthouses where every meal tastes of sea salt and tradition. If you want to truly discover the heart of Ireland—rugged, beautiful, and full of soul—this tour is made for you - and there are only 4 spots left!

NEW - Patagonia ebike Small Group Tour
Dates: November 1 - 7, 2026 - 8 spots only!
Cost: $5400 ($1350 deposit)

Ride an e-bike across the Patagonian steppe and into the shadows of the Paine Massif, stay in remote ranches, meet seasoned baqueanos, spot guanacos and wild horses, and end every day closer to one of Earth’s most iconic parks. It’s more than a vacation—it’s a transformational adventure that challenges, inspires, and delivers a story you’ll remember forever.

I've done this trip twice now - and both times I didn't want it to end - that's how special it is. See some of my highlights from my first trip. It's challenging - you are in remote Patagonia, and you have to be ready for anything weather-wise - but it's one of the most rewarding trips I run. There are only 8 spots available for this trip - act fast and let's head to Patagonia in 2026!

Panama Surf & Yoga Camp - Women Only - 2 spots left!
Dates: January 10-17, 2026
Cost: $3195 ( $800 Deposit)

Ottsworld Blog Posts

Here are a few of my favorite biking tours I've taken around the world - guided and self-guided!

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Ottsworld Travel Discounts

If you want to experience Ireland but couldn't make one of my tours this year - check out Ireland Walk Hike Bike - they do custom tours, group tours, and self-guided itineraries through the west coast of Ireland! Use code OttsWorld2023 for 5% off their offerings - not good with other offers.

Get $100 off at Adventure Life on your next custom trip anywhere in the world. Just tell them Ottsworld sent you!

Get 5% off your Patagonia travels with my friends at Chile Nativo! They will be running my Patagonia ebiking trip and I love them! Use code Ottsworld for 5% off ANY of their regular, non-custom programs (including W hiking and puma tracking).

If you plan a trip to Japan, check out OKU Japan for its incredible multiday hikes and cultural activities in lesser-known areas. Get a 5% Discount for people using code OTTSWORLD5.

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If you've been finding value in these newsletters and the info I've been sharing, please forward this along to any travel-loving friends whom you think might find them useful!

Use these helpful links to book and plan your next trip:

• Schedule a call with me - ditch the overwhelm, avoid the cookie-cutter tourist traps, and craft travel experiences that inspire and energize you. Whether you’re planning your first big adventure, dreaming of a career break, or just need someone to help make sense of it all, I’ve got your back.
• Get my Free ebook Where to Go & When
• Read through my 99 Travel Tips before you go
• Book your travel insurance with the company I use, Allianz Travel Insurance
• Check out my Gear Shop on my Amazon Store

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