Twenty years ago today, I stood in Penn Station with a one-way ticket to Africa to kick off a year-long career break. I thought I was starting a new chapter. I had no idea I was starting an entire novel.
I did not expect any of this. Not the 75+ countries, not the tour company, not the career, and definitely not you — the people who read this thing, take my advice, book the trips, come on my tours, and have somehow stuck around for two decades of me figuring it out in public!
So I’m throwing a party, and you’re all invited. There are 11 prizes from five brands whose gear I actually travel with, and 11 separate winners — because one giant prize means one happy person, and I’d rather have eleven.
Enter below. It’s free, it takes about thirty seconds, and it’s open through September 30th. I’m announcing every winner live on October 4th at my 20-year celebration call, which you should also come to (more on that below).
The Prizes
Two Oboz gift certificates — $200 each (2 winners)
I am a huge fan of the Oboz brand boots and shoes. I use their winter Bridger Insulated hiking boots, their regular Bridger boots, and their Sawtooth Low hiking shoe. I also take the Katabatics or Crosscuts along for light hiking and general travel. Their footbed and arch support are great, and that’s really important to me.
Plus, they are a certified B Corp, and they plant a tree for every pair of shoes sold! Oboz makes footwear that holds up to real mileage on real terrain, and $200 is enough to properly outfit yourself for whatever you’re planning next. Two people are getting one!
Two Thule Compression Cube Sets — $54 each (2 winners)
It took me five years of full-time travel before I started using packing cubes. Five! I thought they were frivolous — an extra thing to buy for a problem I’d already solved with plastic grocery bags. Reader, I had not solved it.
Discovering packing cubes was one of those genuinely life-changing travel moments for me. I lived out of a suitcase for 11 years, and these are the difference between a bag you can actually live out of and a bag you dread opening every night.
I’ve tried a lot of brands since. Most have garbage zippers that fall apart or separate, and many skip compression entirely. These Thule ones are the best I’ve used, full stop — they’re just built better.
Three pairs of Vim & Vigr compression socks — $38 each (3 winners)
This is the one I want you to pay attention to.
In 2018, on what turned out to be the last Niece Project trip, I got off a long flight to India and ended up with three blood clots in my lungs. Pulmonary emboli. I am lucky to be alive — travel, the thing I’ve trusted with my entire adult life, very nearly killed me that year.
I now wear compression socks on every single long flight, and I get up and walk the aisle every 2 hours, and I will talk about it to anyone who will listen. Vim & Vigr makes compression socks that don’t look like medical equipment, which matters more than it should, because the ones you’ll actually wear are the ones that work.
Three of you are getting a pair. Please wear them.
And if you don’t want to wait to win a pair – so pick up your own now with my promo code, OTTSWORLD, and get 15% off your entire order!
Two TESSAN Aero 70 Smart Travel Adapters — $129 each (2 winners)
The single most annoying travel problem nobody warns you about: you’ve got one working outlet, four things that need charging, and a plug that doesn’t fit the wall. The Aero 70 solves all three at once. This is one thing that has really changed in my 20 years of travel…the amount of items you need charging while you travel is crazy.
TESSAN is a newer relationship for me, and I’ve really enjoyed working with them. What I like is that they stay in their lane — electronics and charging, that’s it — and the products are genuinely excellent and have reduced the amount of chargers and plugs that I have to pack!
One TESSAN Magic Charging Station — $49 (1 winner)
Same problem, different setting — this one’s for the nightstand, the desk, or wherever your devices pile up at the end of the day. Wireless charging plus USB-C ports in one thing instead of a tangle of four. Check out the Magic Charging Station!
One Royal Robbins Spotless Collection piece — $120 (1 winner)
Royal Robbins has been making travel clothing since before I started blogging — they were already an established name in 2006, which is not something I can say about many brands I work with now.
The Spotless Collection is exactly what you’re actually hunting for when you’re packing a suitcase: lightweight, quick-drying, and it doesn’t wrinkle. They’re also seriously sustainable, which matters more to me the longer I do this. Winner picks the piece.
How to Enter
Use the widget below. Entering your email gets you in the drawing — everything after that is optional and just gets you more entries.
Ottsworld 20th Anniversary Giveaway
One thing I want to be upfront about: entering adds you to the Ottsworld newsletter. That’s where I send the trip reports, the honest gear opinions, and the tour announcements. You can unsubscribe from any email in one click and it won’t affect your entries at all. If you’d rather enter without joining, there’s a free email alternative in the official rules at the bottom of this post.
The one ‘extra entry’ I’d actually push you toward: share your referral link. You get 3 bonus entries every time someone enters through it, and after 20 years of you telling friends about Ottsworld, this is the one time I can actually thank you for it properly.
Giveaway closes September 30, 2026 at 11:59pm MT.
Open to US and Canada, 18+.
And Come Celebrate on October 4th Online!
I’m drawing all 11 winners live on a video call on October 4th, and I’d love you there whether you win anything or not.
No pitch, no agenda. Just travel talk (bring any questions you want!), a conversation about making the big scary decisions in your own life, how to make travel purposeful, and a chance to raise a glass with people from all over the world who’ve been part of this. Twenty years is worth marking properly.
REGISTER HERE FOR THE VIDEO CALL EVENT!
Thank You
I never wanted a wedding or a nursery, so I’ve never had one of those big everyone-gather-round moments in my life. This is mine, and I’m not going to be shy about it. Thank you for reading, for traveling with me, for telling your friends, and for being supportive of an entire life out of a one-way ticket!
I can hardly wait to see what the next 20 years hold!
Official Rules
NO PURCHASE OR PAYMENT OF ANY KIND IS NECESSARY TO ENTER OR WIN. ENTRY IS FREE. VOID WHERE PROHIBITED BY LAW.
PLEASE NOTE: BY ENTERING THROUGH THE ENTRY FORM YOU WILL BE AUTOMATICALLY SUBSCRIBED TO THE OTTSWORLD EMAIL NEWSLETTER. YOU MAY UNSUBSCRIBE AT ANY TIME USING THE LINK IN ANY EMAIL, AND UNSUBSCRIBING WILL NOT AFFECT YOUR CHANCES OF WINNING. If you would prefer to enter without joining the newsletter, see the free alternate entry method in Section 4.
1. SPONSOR. The Ottsworld 20th Anniversary Giveaway (the “Giveaway”) is sponsored by Ottsworld LLC, a Colorado limited liability company, Denver, Colorado, USA (“Sponsor”). Questions regarding this Giveaway may be directed to sherry@ottsworld.com.
2. ELIGIBILITY. Open to legal residents of the fifty (50) United States and the District of Columbia, and legal residents of Canada (excluding the Province of Quebec), who are eighteen (18) years of age or older, or the age of majority in their province or state of residence, whichever is greater, at the time of entry. Employees, members, and contractors of Sponsor, and the immediate family members (spouse, parent, child, sibling, and their respective spouses) and household members of each, are not eligible. Void in Quebec, Puerto Rico, all U.S. territories and possessions, and wherever else prohibited or restricted by law.
3. ENTRY PERIOD. Begins September 8, 2026 at 12:00:01 a.m. Mountain Time and ends September 30, 2026 at 11:59:59 p.m. Mountain Time. Sponsor’s computer is the official time-keeping device.
4. HOW TO ENTER. During the Entry Period, complete one or more of the entry actions shown on the entry widget on this page. Entrants must provide a valid email address to be eligible. Additional entries may be earned by completing optional bonus actions displayed on the widget, including sharing a unique referral link, following Sponsor’s social media accounts, and visiting designated pages. The number of entries awarded for each action is displayed on the widget. Some actions may be completed once per day during the Entry Period, as indicated.
Newsletter subscription: By submitting your email address through the entry form, you are automatically subscribed to the Ottsworld email newsletter, published by Ottsworld LLC. You may unsubscribe at any time using the unsubscribe link in any email you receive. Unsubscribing does not affect your entries or your chances of winning.
FREE ALTERNATE ENTRY: To enter without joining the newsletter or completing any social media action, send an email with the subject line “20th Anniversary Giveaway Entry” to sherry@ottsworld.com, including your full name, city, state/province, and country. Such entries must be received by September 30, 2026 at 11:59 p.m. MT and will be awarded one (1) entry. Limit one (1) such entry per person.
Entries become the property of Sponsor and will not be returned or acknowledged. Use of any automated system, bot, script, or other device to enter or generate entries is prohibited and will result in disqualification.
5. PRIZES. There are eleven (11) prizes available. Each prize will be awarded to a separate winner. Eleven (11) individual winners will be selected.
Two (2) Oboz Footwear gift certificates — ARV $200.00 USD each
Two (2) Thule Compression Cube Sets — ARV $53.95 USD each
Three (3) pairs of Vim & Vigr compression socks — ARV $38.00 USD each
Two (2) TESSAN Aero 70 Smart Travel Adapters — ARV $129.00 USD each
One (1) TESSAN Magic Charging Station — ARV $49.00 USD
One (1) Royal Robbins Spotless Collection clothing item — ARV $120.00 USD
Total Approximate Retail Value (ARV) of all prizes: $1,048.90 USD.
Prize specifics — including size, color, style, and model — are subject to availability and will be determined by Sponsor or the applicable prize provider in its sole discretion. Gift certificates are subject to the terms, conditions, and expiration dates imposed by the issuer. No substitution, transfer, assignment, or cash redemption of any prize is permitted, except by Sponsor, who reserves the right to substitute a prize of equal or greater value if the advertised prize becomes unavailable. All costs, fees, taxes, and expenses not expressly stated above are the sole responsibility of the winner, including without limitation any customs duties, brokerage fees, or import fees applicable to shipments to Canada. All federal, state, provincial, and local taxes on prizes are the sole responsibility of the winner.
6. ODDS. Odds of winning depend on the total number of eligible entries received during the Entry Period.
7. WINNER SELECTION AND NOTIFICATION. Eleven (11) potential winners will be selected in a random drawing from among all eligible entries received during the Entry Period. The drawing will be conducted on or about October 1, 2026 by Sponsor or its designated giveaway platform, whose decisions are final and binding. Winners will be announced during Sponsor’s online celebration event on October 4, 2026, and will additionally be notified by email at the address provided at entry. Each potential winner must respond to the notification email within five (5) days of the date the notification is sent. If a potential winner does not respond within that period, cannot be contacted, is found to be ineligible, declines a prize, or fails to comply with these Official Rules, the prize may be forfeited and an alternate winner may be selected at random, time permitting. Limit one (1) prize per person and per household.
CANADIAN ENTRANTS — SKILL-TESTING QUESTION: Before being declared a winner, each selected Canadian entrant must correctly answer, without assistance of any kind, whether mechanical or otherwise, a time-limited mathematical skill-testing question administered by email.
8. PUBLICITY. Except where prohibited by law, acceptance of a prize constitutes each winner’s consent to Sponsor’s use of the winner’s first name, last initial, and state or province of residence for promotional purposes in any media, worldwide, without further payment, notice, or consideration.
9. PRIVACY. Information collected from entrants is subject to Sponsor’s Privacy and Disclosure Policy. By entering through the entry form, entrants are automatically subscribed to the Ottsworld email newsletter and consent to receive email communications from Ottsworld LLC. Entrants may unsubscribe at any time, free of charge, using the unsubscribe link contained in every email; unsubscribing after entry does not remove an entrant’s entries or affect their chances of winning. Sponsor does not sell, rent, or share entrant email addresses with the prize providers or any other third party.
10. GENERAL CONDITIONS. By entering, entrants agree to be bound by these Official Rules and by the decisions of Sponsor, which are final and binding in all respects. Sponsor reserves the right, in its sole discretion, to cancel, suspend, terminate, or modify the Giveaway, in whole or in part, if fraud, technical failure, human error, or any other factor beyond Sponsor’s reasonable control impairs the integrity or proper functioning of the Giveaway, and to disqualify any individual it determines to be tampering with the entry process or acting in violation of these Official Rules. Sponsor is not responsible for lost, late, incomplete, misdirected, garbled, or delayed entries; technical, hardware, software, network, or other malfunctions of any kind; or any injury or damage to any person’s device related to participation.
11. LIMITATION OF LIABILITY. By entering, each entrant agrees to release, discharge, indemnify, and hold harmless Sponsor and its respective officers, directors, employees, agents, and the prize providers named in Section 14, from and against any and all claims, liability, injury, loss, or damages of any kind arising out of or in connection with participation in the Giveaway or the acceptance, possession, receipt, use, or misuse of any prize.
12. DISPUTES AND GOVERNING LAW. Except where prohibited, each entrant agrees that all disputes arising out of or connected with this Giveaway shall be resolved individually, without resort to any form of class action, and exclusively in the state or federal courts located in the State of Colorado, United States. These Official Rules are governed by the laws of the State of Colorado, without regard to its conflict of laws principles.
13. NOT AFFILIATED WITH SOCIAL MEDIA PLATFORMS. This Giveaway is in no way sponsored, endorsed, administered by, or associated with Instagram, Facebook, Meta Platforms, Inc., YouTube, Google LLC, Pinterest, TikTok, X/Twitter, or any other social media platform. Entrants understand that they are providing their information to Sponsor and not to any such platform. Any questions, comments, or complaints regarding the Giveaway must be directed to Sponsor.
14. PRIZE PROVIDERS. Prizes are provided to Ottsworld LLC courtesy of Oboz Footwear, Thule, Vim & Vigr, TESSAN, and Royal Robbins. These companies are prize providers only and are not sponsors, administrators, or co-sponsors of this Giveaway.
15. WINNERS LIST. The names of the winners (first name, last initial, and state or province) will be posted on this page within seven (7) days following the October 4, 2026 announcement, and will remain posted for at least thirty (30) days. A written winners list may also be requested by emailing sherry@ottsworld.com no later than December 31, 2026.
Last updated: September 8, 2026
The post 20 Years of Ottsworld — Let’s Celebrate With a Giveaway appeared first on OttsWorld.