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The Destination: Featured Location

Hello Friends,

I decided to start with my fav part of the newsletter and the reason for being here in the first place—the fancy destination.

So, where are we off to this week?

I’ll give you a hint:

Wild roosters and hens roam freely across the island, thanks to Hurricane Iniki setting them loose in 1992. They’re now part of the island’s charm—and your wake-up call.

Do you know?!?!

That’s right—Kauai. It’s one of my favorite places. If I had to pick one place to go every year, it might just be Kauai.

Also, can you imagine a hurricane with a bunch of chickens just blowing around? It was actually probably devastating, but conjurs up a very cartoon image in my mind.

Here are some other notable reasons to pack up this Christmas and visit the island (like I did 2 years ago, and my kids were mad at me because they missed their Christmas program because they “had to go on a vacation.” Brats).

Anyway, here they are:

• Jurassic Park vibes: Kauai’s dramatic cliffs, waterfalls, and jungles doubled as the set for Jurassic Park. A helicopter tour is the ultimate way to see these cinematic landscapes.

• Hidden beaches: Polihale Beach feels like the edge of the earth—miles of golden sand with hardly anyone around. Just don’t forget a 4WD for the bumpy access road!

• Shave ice magic: For the fluffiest, tastiest shave ice, head to local gems like Wailua Shave Ice. Bonus points if you add macadamia nut ice cream on the bottom.

• Na Pali Coast by sea or air: The epic cliffs are stunning from a helicopter or boat, but kayaking along this coast is next-level adventure (if you’re up for a workout).

• Waimea Canyon: Known as the “Grand Canyon of the Pacific,” it’s smaller but more colorful. Try the Pu’u Hinahina lookout for jaw-dropping views.

• Tunnels Beach snorkeling: One of the island’s best underwater spots, where you’ll swim with turtles and colorful reef fish against a backdrop of lush cliffs.

• Hanalei Valley taro fields: This postcard-perfect valley is where you can see the taro plants that fuel Kauai’s iconic poi dishes.

• Random waterfalls: Drive almost anywhere, and you’ll stumble upon cascading waterfalls like Opaeka’a Falls or Wailua Falls (the one from Fantasy Island!).

• Legendary sunsets: Sunsets on the west side (think Polihale or Waimea) will leave you speechless, with the sun sinking into the Pacific in a blaze of colors.

Have you been to Kauai? Do you have a fav island? I would love to hear.

This will likely be the last time I pop in your inbox in 2024—unless I get some wild motivation or something. See ya next year!

-Ashley R. Cummings

The Money: Creative Ways to Earn On The Go

So, what if you don’t want to take your full-fledged career on the go? You know, because getting away sometimes is a break from work. Or what if you just want a little extra cash to support you on your travels?

This week, I’ve been thinking about some fun and creative things I’ve heard other travelers doing to make money while traveling.

Maybe one will strike a chord. Remember, it doesn’t have to be your forever career—but it may help line your pockets while chilling on the Oregon Coast or diving with whale sharks in the Philippines.

Try one of these ideas:

Remote Mystery Shopping
Pose as a customer to evaluate businesses and services.
Get started: Secret Shopper | Market Force

Freelance Tour Guide
Offer niche tours like food crawls or hidden gem explorations.
Get started: Airbnb Experiences

Housesitting or Pet Sitting
Care for homes or pets while enjoying free accommodation.
Get started: TrustedHousesitters

Mobile Massage Therapist or Yoga Instructor
Provide wellness services to travelers or locals.
Get started: How to Start a Mobile Massage Business | Yoga Alliance Certification

Odd Jobs via Gig Apps
Find short-term tasks like errands, organizing, or repairs.
Get started: TaskRabbit

Campervan Advertising
Turn your vehicle into a rolling billboard for extra cash.
Get started: Wrapify | Carvertise

Ship Transporter
Deliver cars, boats, or goods to various destinations.
Get started: uShip

I’ve also heard of people renting their things on platforms like Yoodlize. It might be a good way to pay off that paddle board—or rent one if you don’t want to lug one all around Key West.

Need motivation? Check out these resources

One of the biggest obstacles to embarking on a travel journey is—well—ourselves.

It’s easy to get stuck in the grind and forget to _{permit ourselves} to live our best lives.

If you need a little extra motivation to help give you the push, may I recommend these resources?

• The Wonder Year (Amazon): Fun stories from real worldschooling families. They give advice, to boot.

• Chasing Slow by Erin Loechner (Amazon): A reflective and inspiring memoir about stepping back from the fast-paced grind and embracing a life that prioritizes joy and purpose. Perfect for those dreaming of a simpler, travel-rich life.

• Vagabonding by Rolf Potts (Amazon): A timeless guide to long-term travel and embracing the freedom it offers. It’s packed with practical tips and philosophical insights to get you out the door.

• You Are a Badass by Jen Sincero (Amazon): Need a confidence boost? This funny, no-nonsense book helps you tackle self-doubt, align with your goals, and create a life you love—including one that involves globetrotting.

• The Bucket List Family: Traveling the World Through Adventure by Jessica Gee (Amazon): Written by Jessica Gee herself, this family-centered memoir and guide showcases how to make travel a reality, even with kids in tow. Full of inspiration and practical tips!

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