Winter on Maui – The Ultimate Survival Guide

That’s why you can’t be a true Yankee without winter: because all the best pleasures are earned – the fire, the fried oysters; the warmer seasons, too. Who knows the real worth of summer at the beach without a good taste of the seaside in winter? -Julia Glass

Aloha Hawaii-lovin’ amigos!

In case you don’t follow me on Instagram or Facebook, it’s been a *tad* cold here on Maui the last several days. That quote up there? Yeah, Julia Glass, I’m not a Yankee. Y’all, we don’t do cold here on the Hawaiian Islands (if you live here & you do “do cold” kuddos to you…this post is for the rest of us). It’s snowing on Haleakala today.


If you live on Maui or happen to visit when the weather is weirdly “wintry,” this “Ultimate Survival Guide” will get you through it.


1. Drink hot tea.

Lots of hot tea. Or hot coffee. Or hot water. Just keep drinking hot liquids. Trust me.


2. Over-post on Instagram.

Guilty. When you’re stuck inside due to gloomy, cold, icky weather, you’ve got some time on your hands…so why not over-post on IG? Yeah. It happens.

3. Doodle.

Grab your dusty journal off the desk and go old school, doodling the day away. It’s almost as good as the beach. (I’m gonna keep telling myself that – haha!)

4. Text your friends around the island to find out if the sun is shining where they live.

“Hey! How’s the weather in Kihei?” “What’s it look like on the Westside?”

Jennifer Poppy

We aren’t built for winter!

5. Don’t shave.

Ladies, this is our one opportunity, possibly out of a million, to finally just “go natural.” We’re wearing jeans and socks, so live it up like folks in the rest of the world in winter: skip shaving. (Sorry, no photographic evidence.)

6. Go shopping.

In case you were hiding in a cave over on Hana-side, and did not know, Target just opened last week. Bless. Or shop at a mom-n-pop shop...


Target’s on Maui! Eeee!

7. Dance.

Yeah, dance. Also, pull out your infinity scarf and contemplate these harsh winter days while taking a selfie. It always makes me feel better.

Jennifer Poppy

8. Get your taxes done.

(That one’s for my hubby…love you, sweetie!)

9. Go to work.

Well, no reason to go beach it today…brr!!! Might as well work.

10. Get laughed at by mainlanders.

LOLOLOLOLOLOL – direct quote

11. Remember the good ole’ days of sun and surf…last week.

Word. Hold those memories close to your heart.

Jennifer Poppy

Good times! (Chantelle Kanani Photography)

12. Thank God you live on Maui, and this, too, shall pass!

I had to encourage my kitty today: Hang in there, Layla! It will warm up again, the sun will shine…promise! xoxo

Jennifer Poppy

Winter on Maui – how are you surviving it?

Livin’ la vida aloha,

PS If you enjoyed this “Ultimate Survival Guide,” you may also like “Things Maui Mamas Say When Preparing for a Hurricane.” Also, be sure to subscribe to Island Gypsy Hawaii (via the sidebar) to stay up to date on life on the islands, adventures on Maui, as well as the other Hawaiian islands, and general awesomeness. :)


Travel Maui: How to Fit Hawaiian Culture, Adventure & Beauty into One Morning

For those of you enjoying my Oahu Travel Series, I promise I will be back soon with more of my trip, highlighting some of the lesser-traveled areas, like Northshore & the Windward side. However, today I’m writing about my home island: Maui.

Jennifer Poppy - Hawaiian Paddle Sports

The big question is whether you are going to be able to say a hearty yes to your adventure.

-Joseph Campbell

You’re only on Maui for a week and you really want to experience all that the island has to offer. One way to fulfill that desire is to go on a Hawaiian Paddle Sports tour. Recently my fellow adventure-loving amiga, Bridgett, and I had the opportunity to go on one of their outrigger canoe tours. (It was such a treat to get to “play tourist” on our own island, and we loved every minute of it!)

Jen & Bridgett

Jennifer & Bridgett


While I was impressed with the leadership of our guide, Hawaiian Paddle Sports owner Tim Lara, I was equally impressed by his understanding of Hawaiian culture and the importance of caring for the land. Whether you’re simply visiting Hawaii or live on one of the islands, it is essential to make an effort to learn about Hawaiian history so that you may honor the culture.


Bridgett and I met up at the Ma’alae’a Harbor then headed over to the Westside, driving through a cold wintry rain. I was worried it would still be raining once we arrived, but was pleasantly surprised to find that it was dry and the sun was shining!

Island Gypsy Hawaii - Jennifer Poppy

We arrived at Olowalu Reserve, with friendly faces there to greet us, which was nice since we had no idea about what we were doing. The kind tour guides pointed us in the direction of Tim Lara, our guide for the day, and after signing a waiver, our group of eleven “adventurers” circled up to hear Tim share a glimpse into Hawaiian culture. He began by explaining the value of privilege and responsibility. We share the privilege of enjoying the outdoors, and with that comes the responsibility of cleaning up after ourselves and caring for the people and world around us.


Tim Lara - HPS

Tim Lara – Hawaiian Paddle Sports

I appreciated the fact that Hawaiian Paddle Sports uses reusable water bottles, rather than plastic water bottles for its guests, and offer non-toxic sunscreen as a safer alternative than sunscreens that may harm you and the environment. (I personally use organic coconut oil, as it contains a natural SPF, protecting you and the environment without harmful ingredients.)


After our circle up time, we headed down the beach to our outrigger canoe. We worked as a team to prepare the canoes for our adventure. It was inspirational to hear how the ancient Hawaiians would make canoes from tall, wide koa trees, floating the wood in the ocean for about thirty days to cure it, then preparing the vessel for the sea. Our canoe was made of fiberglass (read about its blessing here), but it was fun imagining how exciting it must have been to finally set off in a handmade koa canoe back in the day!

Before we hopped aboard our outrigger canoe, Tim had us watch for whales as he sang out a Hawaiian chant – “E Ho Mai”.

Jennifer Poppy - Hawaiian Paddle Sports

I found some whales!

With a blow of the conch shell, we were ready to enter the Hawaiian waters on our outrigger canoes. Working as a team, we all made it into our canoes and into the water. I was worried about having to use my arms paddling all morning, and was relieved to find out during our training time that you actually use your entire body to paddle, with power coming up through your legs into your upper-body. Whew! Such a relief because I’m all about that bass (no treble) and knew I could handle paddling that way!

Jennifer Poppy - Hawaiian Paddle Sports

You must live in the present, launch yourself on every wave, find your element in each moment.

-Henry David Thoreau

As we made our way across the water, Tim reminded us that it’s not just one person propelling the canoes, but all twelve of us working together, just as in ancient Hawaiian days when they would travel, paddling in synch with one another. Amazingly, all of us were able to do our part, despite being all different shapes and sizes! I was told that nearly anyone could paddle, and I have to say, it’s true.


We saw several whales breech and fluke, but one of my favorite parts of the whale tour was the ability to actually hear them singing through the hull of the canoe. It’s one thing to hear a recording of a whale or hear one over a ship’s loudspeaker, but it takes the experience to a richer level when you can listen to the whale sing just as they did in days of old, through the canoe’s natural amplification. Add in the fact that you are actually in the water with the singing whale – whoa – mind blowing!



In addition to seeing humpback whales, we also saw honu (sea turtles) and baby reef sharks. I felt 100% safe, even though I’d never been on a canoe in the ocean before. Between our guide’s expertise and my bright red life jacket, I rested easy. (Side note: Bridgett and I were stoked to wear life jackets, as neither one of us had worn one in 20+ years. We were hoping to get a “life jacket selfie” but maybe next time!)


On top of the awesomesauce life jackets, we got to enjoy our most favorite thing: rainbows! Two separate times there were these full rainbows gracing the sky onto the land. Imagine yourself paddling in an outrigger canoe, seeing Hawaiian islands surrounding you, listening to whales singing and enjoying huge rainbows in the sky. That’s a “Maui Moment” right there, and I soaked it all in that morning!


After an amazing couple of hours on the water, we headed back to land. What a wonderful escape from the winter rain! I will cherish my time on that outrigger canoe for years to come…and now the only problem is I want to go again! The ocean is calling my name…and I cannot wait to explore!

Jennifer Poppy - Hawaiian Paddle Sports

Have you ever gone on a whale watching tour or been on an outrigger canoe in the ocean? If you’re looking for a way to enjoy Hawaiian culture, adventure and beauty, this activity is a must!

Livin’ la vida aloha,

*Mahalo Hawaiian Paddle Sports for supplying the beautiful photos for this article. You guys rock! For those interested in an adventure, check out their Maui Kayak Tours, Outrigger Canoe Tours, etc.

If you enjoyed this travel post, then subscribe to Island Gypsy Hawaii for more fun on the islands!

Free Swag and Nine Other Reasons I attended WordCamp Maui

A few weeks ago, my friend Bridgett Loves Maui begged me to go to WordCamp Maui with her. She was excited about the free T-shirts (the WCMaui logo is way cool) and wanted to learn more about using WordPress for her business. Intrigued by the thought of getting to hang out with my friend, meet some new people and learn more about using WordPress, I agreed to go.

Jennifer Poppy - Island Gypsy Hawaii

(The Liza Pierce of A Maui Blog and Bridgett Loves Maui helping me show off our cute WordCamp Maui mugs)

Maybe you’re sitting there wondering what exactly a “WordCamp” is, just as I did a few weeks ago. According to the WordCamp Maui website,

WordCamps are informal, community-organized events that are put together by WordPress users like you. Everyone from casual users to core developers participate, share ideas, and get to know each other.  WordCamps happen all around the world, and each camp has a unique flavor based on the local community.

I’m not a hardcore computer tech genius, however, I do enjoy learning new things and WordPress allows me to write blogs, share my upcycled furniture and art, as well as help other businesses and community websites get off the ground. (I love helping people!) So, if you’re like me, a writer, artist, community-enthusiast, here are nine other reasons (besides the amazing free swag) why I attended WordCamp Maui.

9.  Connect with Maui business owners, photographers, writers, humans.

8. Escape the rain and learn about amazing topics, such as Viral Blogging, Living Off the Grid and Still Doing Business, How to Not Design Like a Develper and How to Self-Publish, just to name a few. (Find links to the slides/video of all the topics here.)

7. Hang out at “The Happiness Bar” – where fresh coffee (yay!) and sweet treats were available for us to scoop up and enjoy, while connecting with other WordCamp Maui speakers and attendees.

6. Take selfies with friends, new and old. Part of connecting is simply having fun, and that is something we most definitely did while attending camp!

Jennifer Poppy & Liza Pierce

5. Gain wisdom from those who have used WordPress for their own businesses and developed amazing brands through it. My friends and I were encouraged by the speakers who were candid in sharing their personal experience and knowledge with us, so we can be successful as well, whatever our ideas of “success” may be in life.


4. Eat gourmet food! Seriously, Maui probably has the best WordCamp food in the world. Soup to Nuts in Wailuku, HI, catered the event, and served out of this world lunches both days!

(Our lunch boxes had fun phrases written on them…everyone had a blast reading them all. Attention to detail makes all the difference.)

3. Hang out with Erik Blair. Need I say more? Also, he is helping bring the Tiny House movement to Maui, so yay!

Word Camp Maui

(Bridgett, me, Erik, Malia, another guy, Tania, living it up at WordCamp Maui. Not pictured: Chris Norberg who took our picture.)

2. Encouragement to find inspiration by spending time outdoors. Several of the guest speakers shared this valuable wisdom, which made my heart go pitter-patter. We live on Maui, after all, inspiration surrounds us for design, writing, photography…the sky is the limit! In fact, on my 15-mile drive from home to the campus where we met, I saw six rainbows (some double-rainbows). Where else in the world can you do that? WordCamp Maui is the best!


1. Okay, I was kidding, the free swag was amazing, hence it deserves a second nod. From free T-shirts, to cool honu stickers, to the fun coffee mugs, a phone case and the food, the first-ever WordCamp Maui was the bomb(d0t)com. Mahalo for doing an outstanding job!

IMG_4993(Pictured: Liza, @heyadamsilver, me & Bridgett.)

Have you ever attended a WordCamp? Looking forward to another one in the future!

Livin’ la vida aloha,