way·ward
\ ˈwā-wərd \
(adj.)
not going or moving in the intended direction
—
About Me
Hi, I’m Alyssa—chronic overthinker, boutique hotel enthusiast, and firm believer that a weekend getaway can be just as fulfilling as a long vacation. Welcome to Wayward, my corner of the internet dedicated to smart, stylish, and accessible travel. I’m so glad you’re here.
A decade ago, while working full-time in higher ed, I started trading movie nights and takeout lunches for budget-friendly weekend trips. With an open mind and a packed itinerary, I made it my mission to experience as much as possible before returning to my desk on Monday morning. Along the way (and after a few mishaps educational moments), I became an expert at finding cheap flights, planning seamless itineraries, and traveling light.
In 2017, after fielding endless questions about how I made it all work, I launched Wayward to share my favorite hidden gems and practical travel tips (trust me, you can only be asked “How do you do it?” so many times…)—all while still juggling a full-time job. With the help of my photographer partner, Michael, I began capturing every detail of my travels, bringing each destination to life through the lens and my stories, while organically growing an incredible community along the way.
Since its early days, Wayward has helped over a million readers plan their best trips yet, becoming a go-to resource for:
- In-depth travel guides to over 100 destinations, both on- and off-the-beaten-path
- Real-life packing lists (because we all know the struggle of over- or under-packing!)
- Boutique hotel reviews that spotlight unique stays
- Curated recommendations for travel, style, and home
- Restaurant roundups and reviews for meals worth your money
And while I love discovering new places more than anything, I also believe in making home a place you love coming back to. That’s why you’ll also find home content and insider guides to my adopted home city, Charlotte, woven throughout the blog.
—
Where to Start?
Looking to shake up your weekends through travel? You’re in the right place! Whether you’re planning a day trip, scoping out cheap flights, searching for the perfect hotel, or choosing the right suitcase, I’ve got you covered:
- How to Find Cheap Flights
- All Travel Guides by Destination
- My Travel Essentials
- All Reviews, Sorted by Brand
- How to Split Travel Costs When One Person Makes More Money
- Twenty Questions You Should Ask a Potential Travel Partner
- What it’s Like to Fly Somewhere for the Day
- The Ultimate Carry-On Luggage Size Guide for U.S. Airlines
- I won a trip! (Now what?)
- Weekend Guide to Richmond, Virginia
- Four Days in Cartagena, Columbia
- Day Trip Guide: Tequila, Mexico
- Checking In: Kings Courtyard Inn in Charleston
- Packing List: Two Weeks in Europe in a Carry-On
- Packing List: Five Days in Mexico City
- My Flight Got Canceled and All I Had to Wear Was This Dress
- Why I Changed My Name at Age 32
Snag your companion ticket and join me on this journey in real-time by signing up for the Wayward newsletter, and by following me on Instagram, TikTok, Pinterest, or LTK. Have a question? Check out the answers to your most Frequently Asked Questions.
—
Contact
I love connecting with fellow travelers and soon-to-be friends in Charlotte! Feel free to drop me a line or message me on Instagram.
Looking to collaborate?
I’m committed to sharing evergreen weekend guides, boutique hotel reviews, innovative travel products, and versatile clothing and accessories with my readers. Visit my Work With Me page for details on partnerships and collaborations.
Note: Wayward does not accept collaborations that do not align with the author’s values. This site does not permit guest posts or participate in link insertion schemes.
—
About those links…
Wayward contains affiliate links to offset the cost of running this site ad-free (because no one likes annoying pop-ups!). When you click an affiliate link and make a purchase, I may earn a small commission—at no extra cost to you. I carefully choose the products and services I feature and frequently turn down partnerships that don’t align with my ethics.
If you choose to support Wayward through these links, thank you! It helps me continue to provide helpful resources for travelers and honest reviews, and I appreciate it so, so much. You can read more about my affiliate policy here.