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Hello Reader ,

What if “someday” didn’t live in that fuzzy future where dreams go to nap… what if someday was 2026?

We all have those trips (or goals) we say we’ll do “when things slow down,” “when I have more time,” or “one of these days.” Trust me, I’ve used those excuses too. But here’s what I’ve learned after almost two decades of chasing adventures around the world:

Life doesn’t magically make space for adventure — we have to decide it’s worth prioritizing.

So what if this was the year you finally:
• tried something new, a little uncomfortable, and wildly rewarding
• hiked trails most tourists don’t even know exist
• cycled through jaw-dropping landscapes with me
• gave yourself permission to do something bold and unforgettable

Let’s make 2026 the year you shake things up!

And lucky you — I have a couple of perfect ways to turn daydreams into plane tickets:

Patagonia E-Bike Adventure – A “Someday” Trip You’ll Actually Do

If Patagonia has been whispering your name, this is your sign. Think soaring mountains, glacial lakes, sweeping pampas, and an e-bike pedal assist that makes epic feel achievable. Small group, incredibly scenic, immersive, fun, and yes… doable.

This is one of those trips people talk about forever because it changes how you see the world and yourself.
​ 👉 Learn more & grab a spot​

And if you'd rather cycle through Europe or the US, check out my other Ottsworld bike trips below!

Join Me at the DIY Trip Summit Jan 13 - 15

If you’re not ready to hop on a plane tomorrow, how about getting inspired, educated, and empowered first? I’ll be presenting at the DIY Trip Summit, talking about one of my absolute favorite topics:

Europe on Foot: Pilgrimage Routes & Hiking Adventures You Haven’t Heard Of

It’s full of the lesser-known long-distance walks, soulful routes, culture-rich experiences, and the kind of slow travel that changes you in the best possible way. So be sure to tune in on Jan. 13th to see my presentation.

The summit is FREE to attend (yes, free!)
Want more bonuses, replays, and extra goodies? Upgrade to a First Class Pass and watch my presentation whenever you want. Plus so many other perks - like a 6 week hiking training plan from personal trainer, Becki Rupp, that I'm giving away.​
And yes — when you sign up, you’re also supporting me, so thank you!

👉 Register for the DIY Trip Summit here​

Need Help Turning “Someday” Into a Real Plan?

If you’re feeling inspired but also a little overwhelmed about where to start — that’s exactly why I offer travel consulting. Whether you want help choosing the right destination, building an adventurous-but-doable itinerary, planning logistics, or figuring out how to make a big dream trip actually happen, I’m here to guide you. Think of it as having a travel-savvy friend in your corner who’s been there, done it, and wants you to experience it too.

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​ 👉 Learn more or book a session​

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So… what if someday wasn’t a vague wish anymore?
What if someday was 2026… and what if you actually said YES?

Let’s make it a year of stories you’ll never stop telling. I’ll be right here cheering you on — and hopefully traveling alongside you!

Where Next?

I'm in Vegas right now, attending the Consumer Electronics Show (CES), checking out the latest travel technology! I've already been so impressed with products for translation, travel safety, and more! Watch my social media for more updates on CES!

Then I'm off to Panama for my favorite way to kick off the year - surf and yoga camp! I hope you'll follow along and get soaked in some inspiration that it's never too late to try new things!

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Happy Travels!

2025 Travel Wrap Up!

Get a little inspiration from my travels last year - nearly 84,000 miles of travel around the globe in 2025! Thank you so much for following along, joining me on my travels and tours, and just supporting what I do. I can't thank you all enough for allowing me to do what I love.

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Ottsworld Tours

🍁 NEW TOUR ALERT: Ride the Capitol Quest with Me 🚲
This fall, I’m opening up something I usually do solo — my Capitol-to-Capitol Quest. Join me cycling from Augusta, Maine to Montpelier, Vermont during peak leaf-peeping season, when New England explodes in golds, reds, and fiery oranges.

Dates: October 7-14, 2026
Cost: $3550 Max: 12 people - only 4 spots remain!

This isn’t just a bike tour — it’s purposeful travel. Quiet backroads, car-free trails, charming small towns, and a front-row seat to one of the most beautiful times of year in the U.S. Every detail is handled, local guides have our backs, and you get to be part of an epic story that connects generations, places, and people.
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Aren't familiar with the Capitol Quest? 👉 See what it is all about! or Watch my YouTube Docuseries on the quest!​

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I have partnered with Maine bike operator ,Summer Feet Cycling, to design and lead the route between capitols. They have come up with a great route that will be scenic, have few cars, and introduce us to their home, the beautiful Northeastern US. In fact - we'll be riding the Cross New Hampshire Adventure trail and the Vermont adventure trail most of the way. These are quiet, gravel roads and trails that will keep us immersed in nature and off the busy roads.

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.

Portugal Cycling Tour with Experience Plus Cycling

Dates: June 2 - 13, 2026
Cost: $6650 - get $200 off with code 'Sherry2026'
(8 day option also possible for June 6 - 13 for $5095 + $200 off w code)

I'm going back to Europe with Experience Plus again next spring! You can join me on this trip hosted by Experience Plus and see Portugal and the Camino de Santiago at a cycling pace. Explore the UNESCO World Heritage sites of Coimbra, Porto, Ponte de Lima and Santiago de Compostela, Spain. Cruise along the Douro, Minho and Lima rivers – on your bike. Take the time to taste and savor the gastronomic specialties and wines of the area.

​See the Itinerary at Experience Plus!​

Ireland Hiking Tour Through Donegal​
Dates: May 16 - 26, 2026 - FULL - Waiting List Only

Other Tours I'm working on launching for 2027:

• South Africa Surf & Safari - February 2027
• Nepal Annapurna Hiking - April 2027
• Spain's Camino Ronda and Catalonia - Sep 2027
• Japan's Michinoku Coastal Trail - Nov 2027

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Ottsworld Blog Posts

As the world returned to travel post-COVID, one thing quickly became clear: most of us don’t want to simply “go back” to travel… we want to travel better. We crave places that feel meaningful, uncrowded, authentic, a bit unexpected — and maybe even a little wild. Whether that means remote landscapes, quiet coastal villages, quirky lesser-known cities, small-town charm, or remote outdoor adventures, travelers are rethinking where and how they explore.

Lucky for you… that’s been my specialty for nearly two decades. That's why I wrote this book. ​

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​

Did you know that you can get my blog posts into your inbox as soon as they are published? Click here to sign up!​!​

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